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CHM 331 > Final > Flashcards

Final Flashcards

1
Q
A

C. only 1 and 2

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2
Q
  1. Which of the following reactions corresponds to a substitution?
    A. propene ® 1,2-dibromopropane
    B. 1-iodopropane ® propene
    C. propene ® propane
    D. 1-iodopropane ® 1-bromopropane
A

D. 1-iodopropane ® 1-bromopropane

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3
Q

10) Which of the following are the substitution products of the reaction shown below?

CH3CH2Br + -OH → ?

A) CH3CH2BrH+ + O-

B) HOCH2CH2Br

C) CH3CH2OH + Br-

D) CH2CH2 + Br- + H2O

E) CH2CHBr + H2O

A

C) CH3CH2OH + Br-

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4
Q
  1. The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction?
    A. the rate remains the same
    B. the rate decreases by a factor of 2
    C. the rate increases by a factor of 2
    D. the rate increases by a factor of 4
A

C. the rate increases by a factor of 2

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5
Q
  1. What is the correct assignment of the names of the following heterocycles?

A. 1 = pyrrole; 2 = thiophene; 3 = pyridine
B. 1 = thiophene; 2 = furan; 3 = pyrrole
C. 1 = furan; 2 = pyrrole; 3 = thiophene
D. 1 = furan; 2 = thiophene; 3 = pyrrole

A

C. 1 = furan; 2 = pyrrole; 3 = thiophene

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6
Q
  1. What is the index of hydrogen deficiency of a compound with a molecular formula of C6H8?
    A. 0
    B. 1
    C. 2
    D. 3
A

D. 3

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7
Q
A

A. 3,4-dimethyl-1-hexen-5-yne

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8
Q
A

C. 3

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9
Q

11) Due to electron delocalization, one would predict that the carbon-oxygen bond in acetamide, CH3CONH2, ________.

A) is nonpolar

B) has more double bond character than the carbon-oxygen bond of acetone, (CH3)2CO

C) is longer than the carbon-oxygen bond of dimethyl ether, (CH3)2O

D) is longer than the carbon-oxygen bond of acetone, (CH3)2CO

E) is formed by overlapping sp3 orbitals

A

D) is longer than the carbon-oxygen bond of acetone, (CH3)2CO

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10
Q
  1. The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?
    A. the rate remains the same
    B. the rate decreases by a factor of 2
    C. the rate increases by a factor of 2
    D. the rate increases by a factor of 4
A

A. the rate remains the same

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11
Q
A

C. ethynylcyclohexane

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12
Q
A

C. 3

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13
Q
  1. The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction?
    A. the rate remains the same
    B. the rate decreases by a factor of 2
    C. the rate increases by a factor of 2
    D. the rate increases by a factor of 4
A

A. the rate remains the same

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14
Q
A

B. (S)-4-methyl-2-hexyne

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15
Q
A

B. 2

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16
Q
A

D. only 1 and 4

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17
Q
A

A. (R)-3-methyl-1-penten-4-yne

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18
Q
A

B. 2

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19
Q
  1. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?
    A. 1-fluorohexane
    B. 1-chlorohexane
    C. 1-bromohexane
    D. 1-iodohexane
A

D. 1-iodohexane

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20
Q
A

B. only 1 and 2

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21
Q
A

C. 3

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22
Q
  1. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?
    A. methyl iodide
    B. ethyl iodide
    C. 2-iodopropane
    D. tert-butyl iodide
A

A. methyl iodide

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23
Q

Which of the following is the strongest acid?
A. propane
B. cyclopropane
C. propene
D. propyne

A

D. propyne

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24
Q
A

C. 3

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25
Q
  1. Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?
    A. methyl iodide
    B. ethyl iodide
    C. 2-bromopropane
    D. tert-butyl chloride
A

A. methyl iodide

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26
Q
  1. Which of the following has the lowest pKa?
    A. butane
    B. 1-butene
    C. 1-butyne
    D. 2-butyne
A

C. 1-butyne

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27
Q
A

C. only 2 and 4

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28
Q
  1. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2?
    A. C5H8O2
    B. C5H10O
    C. C6H15N
    D. C5H10Br2
A

A. C5H8O2

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29
Q

16) Which of the following compounds will undergo an SN2 reaction most readily?

A) (CH3)3CCH2I

B) (CH3)3CCl

C) (CH3)2CHI

D) (CH3)2CHCH2CH2CH2Cl

E) (CH3)2CHCH2CH2CH2I

A

E) (CH3)2CHCH2CH2CH2I

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30
Q
A

B. 1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid

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31
Q
A

B. 2

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32
Q
  1. Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?
    A. tert-butyl fluoride
    B. tert-butyl chloride
    C. tert-butyl bromide
    D. tert-butyl iodide
A

D. tert-butyl iodide

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33
Q
  1. Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 1?
    A. C5H8N2
    B. C5H11N
    C. C6H11N
    D. C5H13NO2
A

B. C5H11N

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34
Q

17) Which of the following is a secondary alkyl halide?

A) CH3Br

B) (CH3)3CBr

C) (CH3)2CHBr

D) (CH3)2CHCH2Br

A

C) (CH3)2CHBr

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35
Q
A

B. 2

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36
Q
  1. Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?
    A. methyl chloride
    B. ethyl chloride
    C. 2-chloropropane
    D. tert-butyl chloride
A

D. tert-butyl chloride

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37
Q
A

D. only 1,3 and 4

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38
Q

18) Which of the following SN2 reactions is the fastest?

A) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br-

B) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr

C) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br-

D) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr

A

A) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br-

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39
Q
A

B. 2

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40
Q
  1. Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH?
    A. methyl fluoride
    B. ethyl bromide
    C. 2-chloropropane
    D. tert-butyl bromide
A

D. tert-butyl bromide

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41
Q
A

D. 4

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42
Q
A

D. i = p;; ii = sp2

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43
Q

19) Which of the following SN2 reactions is the slowest?

A) CH3CH2CHBrCH3 + OH- → CH3CH2CHOHCH3 + Br-

B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr

C) CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br-

D) CH3CH2CH2CH2Br + H2O → CH3CH2CH2CH2OH + HBr

A

B) CH3CH2CHBrCH3 + H2O → CH3CH2CHOHCH3 + HBr

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44
Q
A

B. only 2

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45
Q
A

C. 3

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46
Q
  1. Which of the following does not correspond to a molecular formula of a neutral compound?
    A. C5H5Br
    B. C5H7Cl2
    C. C5H5Br3
    D. C5H8Cl4
A

B. C5H7Cl2

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47
Q
  1. Which of the following is best set of conditions for the preparation of tert-butanol?
    A. tert-butyl fluoride in water
    B. tert-butyl bromide in water
    C. tert-butyl fluoride and NaOH in DMSO
    D. tert-butyl bromide and NaOH in DMSO
A

B. tert-butyl bromide in water

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48
Q
  1. What is the approximate value of the H-C-H bonds angle in ethene?
    A. 90
    B. 109
    C. 120
    D. 180
A

C. 120

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49
Q
A

B. only 2

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50
Q
  1. Which of the following reactions corresponds to a substitution?
    A. tert-butanol ® tert-butyl chloride
    B. tert-butanol ® 2-methylpropene
    C. 3,3-dimethyl-2-butanol ® 2,3-dimethyl-2-butene
    D. cyclohexene ® 1,2-dichlorocyclohexane
A

A. tert-butanol ® tert-butyl chloride

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51
Q

20) Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

A) reaction products when CH3I is used as the substrate

B) reaction products when (CH3)3CCH2I is used as substrate

C) the stereochemistry of nucleophilic substitutions

D) the effect of nucleophile concentration on rate

A

A) reaction products when CH3I is used as the substrate

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52
Q
A

B. only 3

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53
Q
A

B. 2

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54
Q
  1. Which of the following does not correspond to a molecular formula of a neutral compound?
    A. C6H9NO2
    B. C5H7N2O2
    C. C8H12O3
    D. C7H7N
A

B. C5H7N2O2

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55
Q
  1. Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?
    A. tert-butyl fluoride and NaOCH3 in CH3OH
    B. methanol and sodium tert-butoxide in tert-butanol
    C. fluoromethane and sodium tert-butoxide in tert-butanol
    D. tert-butyl bromide and CH3OH
A

D. tert-butyl bromide and CH3OH

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56
Q

21) What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide?

A) (R)-2-pentanol

B) (S)-2-pentanol

C) racemic pentanol

D) 1-pentanol

E) 3-pentanol

A

B) (S)-2-pentanol

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57
Q
A

C. only 3

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58
Q
A

B. 2-methyl-3-heptyne

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59
Q
A

B. 2

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60
Q
  1. What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?
    A. (R) 1-cyano-4-methylhexane
    B. (S) 1-cyano-4-methylhexane
    C. (R) 4-methyl-1-hexene
    D. (S) 4-methyl-1-hexene
A

A. (R) 1-cyano-4-methylhexane

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61
Q
  1. Which of the following does not correspond to a molecular formula of a neutral compound?
    A. C4H8BrNO
    B. C5H9ClN2O
    C. C7H14BrO3
    D. C8H14ClN
A

C. C7H14BrO3

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62
Q
A

C. 3

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63
Q
A

D. 3-methyl-4-nonyne

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64
Q
A

C. 3

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65
Q
  1. What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide?
    A. (R) 2-cyanohexane
    B. (S) 2-cyanohexane
    C. 1-hexene
    D. 2-hexene
A

B. (S) 2-cyanohexane

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66
Q
A

B. 2

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67
Q
  1. Which of the following reaction coordinate diagrams explains the formation of different thermodynamic (T) and kinetic products from the same reactants (R)?
A

C. 3

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68
Q
A

C. (E) 2,3-dibromobutene

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69
Q
A

B. 2

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70
Q
A

A. (E) 3,4-dibromohexene

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71
Q
A

C. 3

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72
Q
A

B. 2

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73
Q
  1. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
    A. -CH(CH3)2
    B. -CH2OCH3
    C. -CH2CH3
    D. -CH2Br
A

D. -CH2Br

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74
Q
A

B. 2,2,3,3-tetrabromobutane

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75
Q
A

D. 4

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76
Q
  1. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds?
    A. -COOH
    B. -Cl
    C. -CH2OH
    D. -CH3
A

B. -Cl

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77
Q
A

D. 3,3,4,4-tetrabromohexane

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78
Q
A

A. 1 > 2 > 3

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79
Q
A

C. only 3

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80
Q
A

D. 2,2-dibromobutane

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81
Q
A

A. 1 > 2 > 3

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82
Q
A

B. 3,5-dimethyl-1,4-hexadiene

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83
Q
A

D. only 1 and 2

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84
Q
A

B. 3,3-dibromohexane

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85
Q
A

A. 1 > 2 > 3

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86
Q
A

A. butanal

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87
Q
A

B. 2

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88
Q
A

B. 2 > 3 > 1

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89
Q

3) Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

A) nonpolar; no dipole

B) polar; δ+ at carbon and δ- at chlorine

C) polar; δ- at carbon and δ+ at chlorine

D) ionic

E) none of the above

A

B) polar; δ+ at carbon and δ- at chlorine

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90
Q

How many alkynes are there with the molecular formula C6H10?
A. 4
B. 5
C. 6
D. 7

A

D. 7

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91
Q
A

C. 3,4-dimethyl-1,3-pentadiene

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92
Q
A

C. 3,4-dimethyl-1,3-pentadiene

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93
Q
A

C. 3,4-dimethyl-1,3-pentadiene

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94
Q
  1. Which of the following statements related to SN1 reactions is not true?
    A. The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion
    B. The charged carbon atom of a carbocation has a complete octet of valence shell electrons
    C. Carbocations are Lewis acids
    D. Nucleophiles seek centers of low electron density
A

B. The charged carbon atom of a carbocation has a complete octet of valence shell electrons

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95
Q
A

D. 1,6-dimethylcyclohexene

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96
Q
A

B. hexanal

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97
Q
A

A. 1

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98
Q
A

D. 2 > 1 > 3

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99
Q
A

A. 1

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100
Q
A

A. butanal

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101
Q
A

D. 4

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102
Q
A

D. only 1 and 2

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103
Q
A

D. cis-4-methyl-1-vinylcyclohexane

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104
Q
A

B. hexanal

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105
Q

33) Identify the most stable structure(s).

A

Answer: A

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106
Q
A

B. allylcyclohexane

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107
Q
A

C. only 3

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108
Q
A

A. 1

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109
Q
  1. In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?
    A. acetic acid
    B. ethanol
    C. water
    D. acetonitrile
A

D. acetonitrile

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110
Q
A

A. only 1

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111
Q
A

D. 4

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112
Q

35) Which of the following is the strongest nucleophile in an aqueous solution?

A) HO-

B) F-

C) Cl-

D) Br-

E) I-

A

E) I-

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113
Q
A

D. OsO4; followed by NaHSO3

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114
Q
A

D. 4

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115
Q
  1. Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?
    A. dimethylsulfoxide
    B. water
    C. hexane
    D. toluene, PhCH3
A

A. dimethylsulfoxide

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116
Q

36) Which of the following is the best leaving group?

A) HO-

B) F-

C) Cl-

D) Br-

E) I-

A

E) I-

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117
Q

36) Which of the following statements concerning resonance contributors and resonance hybrids is not correct?

A) The fewer nearly equivalent resonance contributors are in the structure, the greater the resonance energy.

B) A resonance hybrid is more stable than the predicted stability of any of its resonance contributors.

C) The greater the number of relatively stable resonance contributors, the greater the resonance energy.

D) The greater the predicted stability of a resonance contributor, the more it contributes to the resonance hybrid.

E) none of the above

A

A) The fewer nearly equivalent resonance contributors are in the structure, the greater the resonance energy.

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118
Q
A

C. Br2, H2O

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119
Q
A

D. 4

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120
Q
  1. Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?
    A. water
    B. N,N-dimethylformamide
    C. hexane
    D. toluene, PhCH3
A

B. N,N-dimethylformamide

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121
Q

37) Which of the following species is most reactive in an SN2 reaction?

A) CH3CH2—Cl

B) CH3CH2—Br

C) CH3CH2—I

D) CH3CH2—F

E) CH3CH2—OH

A

C) CH3CH2—I

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122
Q
A

C. B2H6; followed by H2O2, NaOH

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123
Q
A

B. 2

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124
Q
  1. Which of the following anions is the most nucleophilic in polar protic solvents?
    A. F-
    B. Cl-
    C. Br-
    D. I-
A

D. I-

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125
Q

38) Aromatic molecules contain ________ π electrons.

A) no

B) 4n + 2 (with n an integer)

C) 4n + 2 (where n = 0.5)

D) 4n (with n an integer)

E) unpaired

A

B) 4n + 2 (with n an integer)

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126
Q

38) Which of the following species is the least nucleophilic?

A) (CH3)3CO-

B) H2O

C) (CH3)3N

D) BF3

E) CN-

A

D) BF3

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127
Q
A

A. O3; followed by (CH3)2S

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128
Q
  1. Which of the following anions is the most nucleophilic in polar aprotic solvents?
    A. F-
    B. Cl-
    C. Br-
    D. I-
A

A. F-

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129
Q

39) Which of the following is the best nucleophile in water?

A) I-

B) CH3SCH3

C) CH3OCH3

D) Cl-

A

A) I-

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130
Q
  1. How many alkenes have the formula C5H10?
    A. 4
    B. 5
    C. 6
    D. 7
A

C. 6

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131
Q
A

B. Hg(OAc)2 and H2O; followed by NaBH4

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132
Q
A

C. 3

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133
Q
  1. Which of the following compounds is the most nucleophilic in polar protic solvents?
    A. H2O
    B. NH3
    C. H2S
    D. PH3
A

D. PH3

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134
Q

How many terminal alkynes are there with the molecular formula C7H12?
A. 5
B. 7
C. 8
D. 9

A

C. 8

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135
Q
A

C. 3-methyl-1,4-pentadiene

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136
Q
  1. What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation?
    A. 3 C 2p atomic orbital + 3 C sp2 atomic orbital
    B. 3 C 2p atomic orbital + methyl C-H s molecular orbital
    C. 3 C sp2 atomic orbital + methyl C-H s molecular orbital
    D. 3 C 2p atomic orbital + methyl C 2s atomic orbital
A

B. 3 C 2p atomic orbital + methyl C-H s molecular orbital

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137
Q
  1. Which of the following statements related to SN1 reactions is not true?
    A. The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack
    B. Carbocations are electrophilic
    C. The charged carbon atom of a carbocation has an unfilled valence shell
    D. Nucleophiles are Lewis acids
A

D. Nucleophiles are Lewis acids

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138
Q

40) Which of the following statements concerning SN2 reactions of alkyl halides is not correct?

A) The rate of reaction depends on the concentration of the nucleophile.

B) The rate of reaction depends on the concentration of the alkyl halide.

C) The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond.

D) All alkyl iodides react more rapidly than all alkyl chlorides.

E) The rate of reaction depends on the relative nucleophilicity of the nucleophile.

A

D) All alkyl iodides react more rapidly than all alkyl chlorides.

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139
Q
  1. How many constitutional isomeric alkenes are there with the formula C6H12?
    A. 9
    B. 11
    C. 12
    D. 13
A

C. 12

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140
Q
A

D. 4

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141
Q
  1. Which of the following is the most nucleophilic?
    A. sodium ethoxide
    B. acetic acid
    C. methanol
    D. water
A

A. sodium ethoxide

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142
Q

41) Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom.

B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects.

C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.

D) tert-Butoxide is more nucleophilic because it is more basic.

E) none of the above

A

B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects.

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143
Q
  1. How many isomers of 1,6-heptadiene exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

A. 1

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144
Q
A

D. trans-2-butene

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145
Q
  1. Which of the following anions is the best leaving group in an SN1 reaction?
    A. F-
    B. HO-
    C. NH2-
    D. Cl-
A

D. Cl-

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146
Q

42) Which of the following bromides reacts readily via an SN2 reaction with NaN3?

A) C6H5Br

B) CH3CH2CH=CHBr

C) (C6H5)3CBr

D) (CH3)3CCH2CH2CH2Br

E) 1-bromo-1-methylcyclohexane

A

D) (CH3)3CCH2CH2CH2Br

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147
Q
  1. How many isomers of 1,3-heptadiene exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

B. 2

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148
Q
A

B. 2

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149
Q
  1. Which of the following is the best leaving group in an SN2 reaction?
    A. F-
    B. H3C-
    C. CH3O2SO-
    D. HO-
A

C. CH3O2SO-

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150
Q

43) Which halide reacts most rapidly via an SN2 mechanism?

A) (CH3)CCH2CH2F

B) (CH3)CCH2CH2Cl

C) (CH3)CCH2CH2Br

D) (CH3)CCH2CH2I

E) All primary halides react at the same rate in SN2.

A

D) (CH3)CCH2CH2I

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151
Q

43) Which of the following is an aromatic hydrocarbon?

A

C) III

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152
Q
  1. How many isomers of 2,4-heptadiene exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

D. 4

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153
Q
A

C. cis-2-butene

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154
Q

44) Which of the following is aromatic?

A

C) III

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155
Q
  1. How many isomers of 1,3,5-heptatriene exist?
    A. 1
    B. 2
    C. 4
    D. 8
A

C. 4

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156
Q
A

A. 1

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157
Q

45) Which of the structures below would be aromatic?

A

C) III and IV

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158
Q
A

C. cis-2-butene

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159
Q
A

D. 4

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160
Q

46) Which of the following is aromatic?

A

B) II

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161
Q
A

A. 1

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162
Q
A

C. 3

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163
Q

47) Which of the following is aromatic?

A) cyclopentadienyl cation

B) 1,3-cyclohexadiene

C) cyclobutenyl anion

D) 1,3,5-hexatriene

E) cycloheptatrienyl cation

A

E) cycloheptatrienyl cation

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164
Q
A

D. 2 moles of HBr

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165
Q
A

A. 1 > 2 > 3

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166
Q
A

C. only 3

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167
Q
A

A. 1 mole of Br2

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168
Q

49) Which of the following compounds is aromatic?

A

D) IV

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169
Q

49) Which of the following iodides undergoes SN2 reaction with cyanide (CN-) the fastest?

A) 1-iodo-3-methylpentane

B) 2-iodopentane

C) 2-iodo-2-methylpentane

D) 3-iodopentane

E) 1-iodo-2,2-dimethylpentane

A

A) 1-iodo-3-methylpentane

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170
Q
A

D. only 1 and 2

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171
Q
A

B. 1. 3 moles of NaNH2; 2. H3O+

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172
Q
  1. Which of the following is not true regarding alkenes?
    A. alkenes are non polar
    B. alkenes burn in air to give H2O and CO2
    C. alkenes are highly miscible with water
    D. the strongest intermolecular force between alkene molecules is the van der Waals interaction
A

C. alkenes are highly miscible with water

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173
Q
  1. Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide?
    A. the reaction proceeds with inversion of configuration
    B. the rate is proportional to the concentration of sodium cyanide
    C. the rate is proportional to the concentration of (R)-2-bromobutane
    D. the rate of the reaction is independent of the identity of the solvent
A

D. the rate of the reaction is independent of the identity of the solvent

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174
Q
  1. What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?
    A. Rate = k [t-BuBr]
    B. Rate = k [t-BuBr][H2O]
    C. Rate = k [H2O]
    D. Rate = k [t-BuBr]2
A

A. Rate = k [t-BuBr]

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175
Q
A

A. (3S,4E)-3-ethyl-3,4-dimethyl-1,4-hexadiene

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176
Q
A

A. (3S,4E)-3-ethyl-3,4-dimethyl-1,4-hexadiene

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177
Q
  1. Which of the following concepts explains Markovnikov’s rule as applied to the addition of HBr to propene?
    A. the relative stability of carbocations
    B. the nucleophilicity of bromide anion
    C. the acidity of HBr
    D. the Aufbau principle
A

A. the relative stability of carbocations

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178
Q

50) Which of the following is aromatic?

A

A) I

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179
Q
A

C. Na/NH3

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180
Q
  1. Which of the following compounds is most reactive (least stable)?
    A. (Z)-cycloheptene
    B. (E)-cycloheptene
    C. (Z)-cyclooctene
    D. (E)-cyclooctene
A

B. (E)-cycloheptene

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181
Q
  1. Which of the following statements is true regarding the reaction of tert-butyl bromide with water?
    A. the rate is proportional to the concentration of tert-butyl bromide
    B. the rate is proportional to the concentration of water
    C. the rate is independent of the identity of the solvent
    D. the rate of the reaction is independent of the temperature
A

A. the rate is proportional to the concentration of tert-butyl bromide

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182
Q
A

B. H2/Lindlar catalyst

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183
Q
  1. Which of the following is not a characteristic of SN2 reactions?
    A. the electrophilic carbon undergoes inversion of stereochemistry
    B. the rate is proportional to the concentration of substrate
    C. the rate is proportional to the concentration of nucleophile
    D. the rate is independent of the solvent
A

D. the rate is independent of the solvent

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184
Q
A

C. (sia)2BH; followed by H2O2, NaOH

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185
Q
  1. Which of the following is not a characteristic of SN1 reactions?
    A. the electrophilic carbon undergoes inversion of stereochemistry
    B. the rate is proportional to the concentration of substrate
    C. the reaction proceeds faster in a more polar solvent
    D. the rate is independent of the concentration of nucleophile
A

A. the electrophilic carbon undergoes inversion of stereochemistry

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186
Q
A

D. BH3; followed by H2O2, NaOH

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187
Q
A

A. 1

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188
Q
  1. Which of the following statements is not true regarding SN2 reactions?
    A. A carbocation intermediate is formed.
    B. The mechanism has only one step.
    C. Aprotic solvents are good choices for SN1 reactions.
    D. The stereochemical outcome is inversion at the carbon bearing the leaving group.
A

A. A carbocation intermediate is formed.

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189
Q

55) Which of the following is antiaromatic?

A

D) IV

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190
Q
A

D. butanone, CH3COCH2CH3

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191
Q
  1. Which of the following statements is not true regarding SN1 reactions?
    A. A carbocation intermediate is formed.
    B. The mechanism has only one step.
    C. Polar, protic solvents are good choices for SN1 reactions.
    D. The stereochemical outcome is racemization at the carbon bearing the leaving group.
A

B. The mechanism has only one step.

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192
Q

56) Identify the alkyl halide that reacts the fastest in an SN1 reaction.

A) 2-chloro-2-methylpropane

B) 2-chlorobutane

C) 1-chlorobutane

D) chloromethane

A

A) 2-chloro-2-methylpropane

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193
Q
A

C. (Z)-6-phenyl-2-hexene

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194
Q

57) Identify the alkyl halide that reacts the fastest in an SN1 reaction.

A) 2-chloropropane

B) 2-bromopropane

C) 2-fluoropropane

D) 2-iodopropane

A

D) 2-iodopropane

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195
Q
A

D. heptane

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196
Q
A

B. (E)-2-heptene

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197
Q
A

D. only 1 and 2

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198
Q

6) Which of the following pairs are resonance structures?

A

C) III

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199
Q

6) Which of the following pairs are resonance structures?

A

C) III

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200
Q

6) Which of the following pairs are resonance structures?

A

C) III

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201
Q
  1. What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism?
    A. Rate = k [BuCl]
    B. Rate = k [BuCl][NaI]
    C. Rate = k [NaI]
    D. Rate = k [BuCl]2
A

B. Rate = k [BuCl][NaI]

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202
Q
A

C. 3

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203
Q

63) Which of the following factors has no effect on the rate of SN1 reactions?

A) the nature of the alkyl halide

B) the nature of the leaving group

C) the concentration of the alkyl halide

D) the concentration of the nucleophile

E) the value of the rate constant

A

D) the concentration of the nucleophile

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204
Q

64) Which of the following statements about the π molecular orbital description of cyclobutadiene is not correct?

A) Cyclobutadiene has two degenerate nonbonding π molecular orbitals.

B) Cyclobutadiene has a single bonding π molecular orbital.

C) Cyclobutadiene has two electrons in nonbonding π molecular orbitals.

D) Cyclobutadiene has one electron in an antibonding π molecular orbital which makes it antiaromatic.

E) none of the above

A

D) Cyclobutadiene has one electron in an antibonding π molecular orbital which makes it antiaromatic.

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205
Q

65) Which of the following is the rate law for SN1 mechanisms?

A) Rate = k[Alkyl Halide] [Nucleophile]

B) Rate = k[Nucleophile]

C) Rate = k[Alkyl Halide]

D) Rate = k[Alkyl Halide] [Nucleophile] + k2[Alkyl Halide]

E) Rate = k1[Alkyl Halide] + k2[Nucleophile]

A

C) Rate = k[Alkyl Halide]

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206
Q

66) Which of the following is an allylic cation?

A

B) II

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207
Q

67) Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

A) cyclohexyl bromide

B) methyl iodide

C) isopropyl chloride

D) 3-chloropentane

E) 3-iodo-3-methylpentane

A

E) 3-iodo-3-methylpentane

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208
Q

67) Which of the following is a benzylic cation?

A

D) IV

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209
Q

68) In the SN1 hydrolysis mechanism of (CH3)3CBr, there are ________ elementary steps, ________ distinct transition states, and ________ distinct intermediates.

A) 2, 2, 2

B) 2, 2, 3

C) 2, 3, 2

D) 3, 2, 3

E) 3, 3, 2

A

E) 3, 3, 2

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210
Q

68) Which of the following is the most stable cation?

A

C) III

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211
Q
  1. Which of the following sets consists of only polar aprotic solvents?
    A. water, hexane, methanol
    B. acetic acid, DMF, toluene
    C. DMSO, ethanol, acetonitrile
    D. DMF, acetonitrile, DMSO
A

D. DMF, acetonitrile, DMSO

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212
Q

69) How many allylic hydrogen atoms are present in the following molecule?

A

E) zero

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213
Q
  1. Which of the following sets consists of only polar protic solvents?
    A. water, DMF, DMSO
    B. acetic acid, methanol, water
    C. DMSO, ethanol, acetonitrile
    D. DMF, acetonitrile, DMSO
A

B. acetic acid, methanol, water

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214
Q

7) Identify the alkyl halide that reacts the fastest in a SN2 reaction.

A) 2-chloro-2-methylpropane

B) 2-chlorobutane

C) 1-chlorobutane

D) chloromethane

A

D) chloromethane

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215
Q

7) Which of the following pairs are resonance structures?

A

C) III

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216
Q
A

B. 3 > 1 > 2

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217
Q
  1. What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)?
    A. Rate = k [i-PrBr]
    B. Rate = k [i-PrBr]2
    C. Rate = k [NaOCH3]
    D. Rate = k [i-PrBr][NaOCH3]
A

D. Rate = k [i-PrBr][NaOCH3]

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218
Q

70) How many benzylic hydrogens are present in the following molecule?

A

E) zero

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219
Q

71) Which of the following is the most stable diene?

A

C) III

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220
Q

74) What descriptive term is applied to the type of diene represented by 2,4-hexadiene?

A) conjugated diene

B) cumulated diene

C) isolated diene

D) alkynyl diene

E) none of the above

A

A) conjugated diene

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221
Q

74) Which of the following iodides undergoes SN1 solvolysis in water the fastest?

A) 1-iodo-3-methylpentane

B) 2-iodopentane

C) 2-iodo-2-methylpentane

D) 3-iodopentane

E) 1-iodo-2,2-dimethylpentane

A

C) 2-iodo-2-methylpentane

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222
Q

75) What descriptive term is applied to the type of diene represented by 1, 5-octadiene?

A) conjugated diene

B) cumulated diene

C) isolated diene

D) alkynyl diene

E) none of the above

A

C) isolated diene

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223
Q

76) Which of the following is a cumulated diene?

A

C) III

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224
Q

77) Which of the following is a conjugated diene?

A

A) I

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225
Q

8) Identify the alkyl halide that reacts the fastest in an SN2 reaction.

A) 1-chloropropane

B) 1-bromopropane

C) 1-fluoropropane

D) 1-iodopropane

A

D) 1-iodopropane

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226
Q

8) Which of the following is not a resonance structure of the species shown?

A

D) IV

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227
Q

8) Which of the following is not a resonance structure of the species shown?

A

D) IV

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228
Q
A

D. i = sp2; ii = sp2; iii = sp3

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229
Q
  1. What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol?
    A. Rate = k [i-PrBr]
    B. Rate = k [i-PrBr]2
    C. Rate = k [CH3OH]
    D. Rate = k [i-PrBr][CH3OH]
A

A. Rate = k [i-PrBr]

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230
Q
A

B. 2

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231
Q

80) SN1 reactions usually proceed with ________.

A) equal amounts of inversion and retention at the center undergoing substitution

B) slightly more inversion than retention at the center undergoing substitution

C) slightly more retention than inversion at the center undergoing substitution

D) complete inversion at the center undergoing substitution

E) complete retention at the center undergoing substitution

A

B) slightly more inversion than retention at the center undergoing substitution

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232
Q

85) Identify the halide(s) that react in a SN2 reaction.

A) benzyl bromide

B) bromobenzene

C) 1-bromo-1-butene

D) 1-bromo-2-butene

E) 2-bromo-2-phenylpropane

A

A and D

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233
Q

86) Identify the most stable carbocation.

A
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234
Q

87) Identify the most stable carbocation.

A
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235
Q

88) Which of the following is classified as a vinyl halide?

A) CH3CHCHOH

B) CH3CHCHCl

C) CH3CHCHCH2Cl

D) CH3CH2CH2CH2Br

E) BrCH2CHCH2

A

B) CH3CHCHCl

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236
Q

9) Identify the strongest nucleophile in an SN2 reaction.

A) isopropoxide ion

B) tert-butoxide ion

C) ethoxide ion

D) tert-pentoxide ion

A

C) ethoxide ion

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237
Q

9) In which of the following does resonance delocalization of electron density not play a role?

A) allyl cation

B) benzyl anion

C) CO32-

D) O3

E) cyclohexyl radical

A

E) cyclohexyl radical

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238
Q
  1. The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction?
    A. the rate remains the same
    B. the rate decreases by a factor of 2
    C. the rate increases by a factor of 2
    D. the rate increases by a factor of 4
A

C. the rate increases by a factor of 2

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239
Q
A

C. 1 = pyridine; 2 = thiophene; 3 = furan

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240
Q
  1. What is the index of hydrogen deficiency of a compound with a molecular formula of C5H10?
    A. 0
    B. 1
    C. 2
    D. 3
A

B. 1

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241
Q
A

B. 2

242
Q

96) Which of the following is/are the major product(s) of the following reaction?

A

A) I

243
Q

97) Which of the following is the strongest acid?

A
244
Q

98) Which of the following is the strongest acid?

A

D) IV

245
Q

Aromatic, not aromatic, or antiaromatic?

A

not aromatic

246
Q

Aromatic, not aromatic, or antiaromatic?

A

Not aromatic

247
Q

Aromatic, not aromatic, or antiaromatic?

A

Aromatic

248
Q

Aromatic, not aromatic, or antiaromatic?

A

not aromatic

249
Q

Aromatic, not aromatic, or antiaromatic?

A

antiaromatic

250
Q
A

C. only 1 and 2

251
Q
  1. Which of the following is not one of Hückel’s criteria for aromaticity?
    A. The compound must be cyclic
    B. The compound must have one p-orbital on each atom of a ring
    C. The compound must be planar or nearly planar so that there is a continuous overlap of p orbitals
    D. The compound must have a closed loop of six pi electrons
A

D. The compound must have a closed loop of six pi electrons

252
Q
  1. What is the approximate value of the C-C-C bond angle in propene?
    A. 90
    B. 109
    C. 120
    D. 180
A

C. 120

253
Q
  1. Which of the following concepts explains why tertiary carbocations are more stable than primary and secondary carbocations?
    A. electronegativity
    B. resonance
    C. hyperconjugation
    D. the octet rule
A

C. hyperconjugation

254
Q

What is the approximate C-C-C bond angle in propyne?
A. 90
B. 109
C. 120
D. 180

A

D. 180

255
Q

Heterocyclic compound

A

Has a ring of atoms other than carbon

256
Q

If the conjugated diene is not symmetrical, what do you do?

A

Protonate to form the more stable carbocation

257
Q

monocyclic hydrocarbons with alternating single and double bonds

A

annulenes

258
Q

most of the time, the 1,2 addition product is the …

A

kinetic product

259
Q

most of the time, the 1,4-addition product is the

A

thermodynamic product

260
Q

The kinetic product predominates when the reaction is….

A

irreversible

1,2-addition

261
Q

The thermodynamic product predominates when the reaction is…

A

reversible

262
Q

What is the hybridization of the nitrogen atom of pyridine?
A. s
B. sp
C. sp2
D. sp3

A

C. sp2

263
Q

What is the hybridization of the oxygen atom of furan?
A. s
B. sp
C. sp2
D. sp3

A

C. sp2

264
Q

What is the IUPAC name of the following compound?

(CH3)2CHCH2-CºC-CH(CH3)2
A. 2,6-dimethyl-3-heptyne
B. 2,6-dimethyl-4-heptyne
C. 1,1,5,5-tetramethyl-2-pentyne
D. 4-nonyne

A

A. 2,6-dimethyl-3-heptyne

265
Q

What is the IUPAC name of the following compound?

CH3CH2CH2-CºC-CH(CH3)2
A. 1-isopropyl-1-pentyne
B. 2-methyl-3-heptyne
C. 6-methyl-4-heptyne
D. isopropyl propyl ethyne

A

B. 2-methyl-3-heptyne

266
Q

What is the kinetic product obtained from the addition of 1 mole of bromine to 1,3-butadiene?
A. 3,4-dibromo-1-butene
B. (E)-1,4-dibromo-2-butene
C. (Z)-1,4-dibromo-2-butene
D. (Z)-2,3-dibromo-2-butene

A

A. 3,4-dibromo-1-butene

267
Q

What is the reactive intermediate in the reaction of 1,3-butadiene with HBr resulting in 1,2-addition?
A. cyclic bromonium cation
B. allylic cation
C. allylic radical
D. dienophile

A

B. allylic cation

268
Q

What is the relative stability of carbocations?

A

benzyl cation ~ allyl cation ~ tertiary carbocation > secondary carbocation > primary carbocation > methyl cation > vinyl cation

269
Q

What is the smallest cycloalkyne that is stable at room temperature?
A. cyclohexyne
B. cyclononyne
C. cyclododecyne
D. cycloeicosyne

A

B. cyclononyne

270
Q

What is the thermodynamic product obtained from the addition of 1 mole of bromine to 1,3-butadiene?
A. 3,4-dibromo-1-butene
B. (E)-1,4-dibromo-2-butene
C. (Z)-1,4-dibromo-2-butene
D. (Z)-2,3-dibromo-2-butene

A

B. (E)-1,4-dibromo-2-butene

271
Q

What is this?

A

Tertiary benzylic cation

272
Q
A

purine

273
Q
A

pyrimidine

274
Q

What is this?

A

secondary allylic cation

275
Q

What is this?

A

Secondary benzylic cation

276
Q

What is this?

A

Benzyl cation

277
Q

What is this?

A

Tertiary allylic cation

278
Q

What is this?

A

vinyl cation

279
Q
A

pyrrole

280
Q
A

Furan

281
Q

What is this?

A

secondary alkyl carbocation

282
Q

What is this?

A

Allyl cation

283
Q
A

thiophene

284
Q
A

quinoline

285
Q
A

indole

286
Q
A

pyridine

287
Q
A

imidazole

288
Q

What type of intermediate s formed in the Hg2- catalyzed hydration of an alkyne??
A. an alcohol
B. an enol
C. a 1,2-diene
D. an epoxide

A

B. an enol

289
Q

What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol?
A. nucleophilic addition
B. electrophilic addition
C. radical addition
D. elimination

A

B. electrophilic addition

290
Q

What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide?
A. nucleophilic addition
B. electrophilic addition
C. radical addition
D. elimination

A

B. electrophilic addition

291
Q

What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?
A. carbocation
B. carbanion
C. radical
D. cyclic bromonium ion

A

A. carbocation

292
Q

What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a bromohydrin?
A. carbocation
B. carbanion
C. radical
D. cyclic bromonium ion

A

D. cyclic bromonium ion

293
Q

What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol?
A. carbocation
B. carbanion
C. radical
D. carbene

A

A. carbocation

294
Q

Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne?
A. 2s + sp
B. sp + sp2
C. sp + sp3
D. sp2 + sp3

A

C. sp + sp3

295
Q

Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne?
A. 2s + 2s; sp + sp; 2p + 2p
B. sp + sp; sp + sp; 2p + 2p
C. sp + sp; 2p + 2p; 2p + 2p
D. sp2 + sp2; sp + sp; 2p + 2p

A

C. sp + sp; 2p + 2p; 2p + 2p

296
Q

Which of the following compounds is antiaromatic?
A. ethane
B. cyclobutadiene
C. benzene
D. cyclooctatetraene

A

B. cyclobutadiene

297
Q

Which of the following compounds is aromatic?
A. ethane
B. cyclobutadiene
C. benzene
D. cyclooctatetraene

A

C. benzene

298
Q

Which of the following is not a major organic product obtained from the addition of 1 mole of bromine to (E)-1,3-pentadiene?
A. (E)-4,5-dibromo-2-pentene
B. 3,4-dibromo-1-pentene
C. (E)-1,4-dibromo-2-pentene
D. (E)-1,2-dibromo-2-pentene

A

D. (E)-1,2-dibromo-2-pentene

299
Q

Which of the following is not true about cyclooctatetraene?
A. The planar conformation is antiaromatic
B. In the planar conformation there are two electrons in degenerate nonbonding pi orbitals.
C. In the tub conformation the pi system is not conjugated
D. The tub conformation is aromatic

A

D. The tub conformation is aromatic

300
Q

Which of the following reactions of alkenes is not stereospecific?
A. bromination (treatment with Br2 in CHCl3)
B. hydrogenation (treatment with H2/Pt)
C. acid-catalyzed hydration (treatment with aqueous H2SO4)
D. bromohydrin formation (treatment with Br2/H2O)

A

C. acid-catalyzed hydration (treatment with aqueous H2SO4)

301
Q

Which of the following reactions of alkenes is stereospecific?
A. addition of HCl (treatment with HCl)
B. hydrogenation (treatment with H2/Pt)
C. addition of HBr (treatment with HBr)
D. acid-catalyzed hydration (treatment with aqueous H2SO4)

A

B. hydrogenation (treatment with H2/Pt)

302
Q

Which of the following reactions of alkenes takes place with anti stereospecificity?
A. bishydroxylation (treatment with OsO4 followed by NaHSO3)
B. hydrogenation (treatment with H2/Pt)
C. addition of HBr (treatment with HBr)
D. bromohydrin formation (treatment with Br2, H2O)

A

D. bromohydrin formation (treatment with Br2, H2O)

303
Q

Which of the following reactions of alkenes takes place with syn stereospecificity?
A. addition of bromine (treatment with Br2)
B. hydrogenation (treatment with H2/Pt)
C. addition of HBr (treatment with HBr)
D. acid-catalyzed hydration (treatment with aqueous H2SO4)

A

B. hydrogenation (treatment with H2/Pt)

304
Q

Which of the following statements is not true about the structure of benzene?
A. six atomic 2p-orbitals overlap to form six p-molecular orbitals
B. there are three bonding p-molecular orbitals and three p-antibonding molecular orbitals
C. the ground state electronic configuration of benzene has six electrons in three p-bonding molecular orbitals
D. the bonds alternate in length around the ring

A

D. the bonds alternate in length around the ring

305
Q

Which of the following statements is not true about the structure of benzene?
A. the carbon-carbon bonds are all the same length
B. the structure rapidly transforms between two resonance contributors
C. the structure is an average of two resonance contributors
D. the ring of six carbon atoms is planar

A

B. the structure rapidly transforms between two resonance contributors

306
Q

Which of the following terms describes the mechanism for the addition of Br2 to butadiene?
A. electrophilic addition
B. nucleophilic addition
C. pericyclic addition
D. conjugate addition

A

A. electrophilic addition

307
Q

Which orbital contains the lone pair on the nitrogen atom of pyrrole?
A. s
B. p
C. sp
D. sp2

A

B. p

308
Q

Which orbital contains the lone pair on the nitrogen atom of pyridine?
A. s
B. p
C. sp
D. sp2

A

D. sp2

309
Q

Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne
A. Treatment with Br2; followed by treatment with NaNH2
B. Treatment with Br2, H2O; followed by treatment with NaOH
C. Treatment with Br2; followed by treatment with H2SO4
D. Treatment with HBr; followed by treatment with NaOH

A

A. Treatment with Br2; followed by treatment with NaNH2

310
Q

Which sequence of reactions can be used to convert 1-pentene to 1-pentyne
A. Treatment with HBr; followed by treatment with NaOH
B. Treatment with Br2; followed by treatment with NaNH2
C. Treatment with Br2; followed by treatment with H2SO4
D. Treatment with Br2, H2O; followed by treatment with NaOH

A

B. Treatment with Br2; followed by treatment with NaNH2

311
Q

Which of the following reagents react with 2-butyne to form butane
A. H2/Lindlar catalyst
B. H2/Pd
C. (sia)2BH followed by CH3COOH
D. Na/NH3

A

B. H2/Pd

312
Q
  1. What is(are) the major organic product(s) obtained from the following substitution reaction?
A

D. 1, 2 and 3

313
Q
  1. What is(are) the major organic product(s) obtained from the following substitution reaction?
A

D. 1, 2 and 3

314
Q
  1. Which of the following energy diagrams represents the course of an exothermic SN1 reaction?
A

A. 1

315
Q
  1. Which of the following energy diagrams represents the course of an exothermic SN2 reaction?
A

C. 3

316
Q

1) What is the nucleophile in the reaction shown below?

A

B) II

317
Q

2) Which of the following is not a nucleophile?

A

C) +CH3

318
Q

4) Which of the following is not normally considered to be a nucleophile?

A

D) CH3CH2+

319
Q

11) Which of the following alkyl halides gives the slowest SN2 reaction?

A
320
Q

12) Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN2 reaction?

A

B) doubles the rate

321
Q

13) Assuming no other changes, what is the effect of doubling both the alkyl halide and the nucleophile concentrations in the above reaction?

A) no change

B) doubles the rate

C) triples the rate

D) quadruples the rate

E) rate is halved

A

D) quadruples the rate

322
Q

14) Which of the following SN2 reactions is the fastest?

A

B) CH3CH2CH2I + HO- → CH3CH2CH2OH + I-

323
Q

15) Which of the following SN2 reactions is the slowest?

A
324
Q

44) Which halide reacts most rapidly via an SN2 mechanism?

A

E

325
Q

45) Which halide reacts most rapidly via an SN2 mechanism?

A

Answer: E

326
Q

59) Assuming no other changes, what is the effect of doubling only the concentration of the nucleophile in the above reaction?

A) no change

B) doubles the rate

C) triples the rate

D) quadruples the rate

E) rate is halve

A

A) no change

327
Q

60) Assuming no other changes, what is the effect of doubling both the concentration of the alkyl halide and the nucleophile in the above reaction?

A) no change

B) doubles the rate

C) triples the rate

D) quadruples the rate

E) rate is halved

A

B) doubles the rate

328
Q

64) Which of the following carbocations is the most stable?

A

C

329
Q

66) Which of the following carbocations is the least stable?

A

A) I

330
Q

78) When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-, the product is the compound shown below. What is/are the configuration(s) of the product(s) obtained from this reaction?

A

B) R only

331
Q

87) Which of the following can’t undergo nucleophilic substitution reactions?

A

B) II

332
Q
  1. Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF?
A

A. 1

333
Q
  1. Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water?
A

B. 2

334
Q
  1. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?
A

A. 1

335
Q
  1. Which of the following represents the transition state of the reaction between methyl iodide and ammonia?
A

C. 3

336
Q
  1. Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3
A

D. 4

337
Q

58) Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN1 reaction?

A) no change

B) doubles the rate

C) triples the rate

D) quadruples the rate

E) rate is halved

A

B) doubles the rate

338
Q

61) Which of the following alkyl halides gives the fastest SN1 reaction?

A

C

339
Q

62) Which of the following alkyl halides gives the fastest SN1 reaction?

A

C

340
Q

82) When (S)-1-bromo-1 phenylethane undergoes an SN1 reaction with methanethiol (CH3SH), the product is the compound shown. What is/are the configuration(s) of the product obtained from this reaction?

A

D) a mixture of the enantiomers, with slightly more R than S

341
Q

93) Which of the following solvents is aprotic?

A

C) CH3CH2OCH2CH3

342
Q

94) Which of the following solvents is protic?

A

D) CH3CH2OH

343
Q

105) What is the leaving group in the reaction shown below?

A

A

344
Q

110) Give the name(s) of the product(s) for the following SN2 reaction.

A

C) (S)-3-hexanol

345
Q

95) Protic and aprotic solvents are very similar as solvents except for their ________.

A) polarity

B) dielectric constant

C) ability to stabilize anions by hydrogen bonding

D) ability to stabilize cations by hydrogen bonding

E) ability to stabilize cations with unshared pairs of electrons

A

C) ability to stabilize anions by hydrogen bonding

346
Q

96) Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

A) The substrate is more soluble in polar solvents.

B) The substrate is less soluble in polar solvents.

C) The nucleophile is solvated by polar solvents.

D) Solvation by polar solvents stabilizes the carbocation.

E) Solvation by polar solvents stabilizes the transition state.

A

E) Solvation by polar solvents stabilizes the transition state.

347
Q

97) Which of the following statements is generally true for SN1 reactions?

A) Complete inversion of configuration occurs.

B) These reactions are favored by nonpolar solvents.

C) These reactions are favored by polar solvents.

D) Reaction rates depend only on the concentration of the nucleophile.

E) The mechanism is a one-step back attack.

A

C) These reactions are favored by polar solvents

348
Q

98) The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone. Why?

A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.

B) The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.

C) The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.

D) The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride.

E) none of the above

A

A) The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.

349
Q

107) Give the SN2product(s) for the reaction of (R)-2-bromopentane with an excess of sodium methoxide.

A) (S)-2-methoxypentane

B) (R)-2-methoxypentane

C) (S)-2-ethoxypentane

D) (R)-2-ethoxypentane

E) (R)-2-pentanol

F) (S)-2-pentanol

A

A) (S)-2-methoxypentane

350
Q

108) Give the name(s) of the product(s) of the SN2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

A) 2,2-dimethyl-1-butanol

B) 3,3-dimethyl-2-butanol

C) 3,3-dimethyl-1-butanol

D) 2,3-dimethyl-2-butanol

E) 2,3-dimethyl-1-butanol

A

B) 3,3-dimethyl-2-butanol

351
Q

109) Give the name(s) of the product(s) of the SN1 reaction of 3-bromo-2,2-dimethylbutane with water.

A) 2,2-dimethyl-1-butanol

B) 3,3-dimethyl-2-butanol

C) 3,3-dimethyl-1-butanol

D) 2,3-dimethyl-2-butanol

E) 2,3-dimethyl-1-butanol

A

D) 2,3-dimethyl-2-butanol

352
Q

113) Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

A) (R)-2-bromo-3-ethylpentane

B) (S)-2-bromo-3-ethylpentane

C) (R)-3-bromo-2-methylpentane

D) (S)-3-bromo-2-methylpentane

E) 3-bromo-3-ethylpentane

A

E) 3-bromo-3-ethylpentane

353
Q

114) Which of the following alkyl bromides is likely to undergo rearrangement by a 1, 2-methyl shift?

A) benzyl bromide

B) 2-bromo-3-ethylpentane

C) 3-bromo-3-methylpentane

D) 2-bromo-3, 3-dimethylpentane

E) 3-bromo-2, 3-dimethylpentane

A

D) 2-bromo-3, 3-dimethylpentane

354
Q

115) A 1,2-methyl shift occurs when which of the following iodides is heated in ethanol?

A) C6H5CHICH(CH3)2

B) (CH3)2CHCHICH3

C) (CH3)3CCH2CH2I

D) (CH3)2C=CHI

E) (CH3)3CCHICH2CH3

A

E) (CH3)3CCHICH2CH3

355
Q

106) What compound results from the 1, 4-addition of one equivalent of HBr to 1, 3-butadiene?

A) 1-bromo-1-butene

B) 2-bromo-2-butene

C) 4-bromo-1-butene

D) 3-bromo-1-butene

E) 1-bromo-2-butene

A

E) 1-bromo-2-butene

356
Q

103) Which of the following is/are the main product(s) of the following reaction?

A

E) A and C

357
Q

104) What is/are the product(s) from the following reaction?

A

D) I is major, II is minor

358
Q

105) What is/are the product(s) of the following reaction?

A

E) I and III

359
Q

107) Which of the following is/are the major product(s) of the following reaction?

A

C) II

360
Q

108) What is/are the product(s) from the following reaction?

A

A) I and II

361
Q

119) Which of the following is a correct statement considering thermodynamic versus kinetic control of organic reactions?

A) When a reaction is under thermodynamic control, the relative amounts of products depend on the activation energies of the steps leading to their formation.

B) The kinetic product always predominates when the reaction is reversible.

C) Higher temperatures and longer reaction times typically favor the kinetic product over the thermodynamic product.

D) When the products are in equilibrium under the reaction conditions, the relative amounts of products depend on their stabilities and the reaction is under thermodynamic control.

E) none of the above

A

D) When the products are in equilibrium under the reaction conditions, the relative amounts of products depend on their stabilities and the reaction is under thermodynamic control.

362
Q

133) Which of the following terms best describes a Diels-Alder reaction?

A) a [4+2] cycloaddition

B) a [2+2] cycloaddition

C) a sigmatropic rearrangement

D) a 1, 3-dipolar cycloaddition

E) a substitution reaction

A

A) a [4+2] cycloaddition

363
Q

134) When 1, 3-butadiene reacts with CH2CHCN, which of the terms below best describes the product mixture?

A) a mixture of two diastereomers

B) a single compound

C) a racemic mixture

D) optically active

E) a mixture of bicyclic compounds

A

C) a racemic mixture

364
Q

135) The Diels-Alder reaction is a concerted reaction; this means that ________.

A) a mixture of endo and exo products is formed

B) all bond making and bond breaking occurs simultaneously

C) the products contain rings

D) the reaction follows Markovnikov’s rule

E) the reaction is highly endothermic

A

B) all bond making and bond breaking occurs simultaneously

365
Q

136) Which of the following statements is (are) true of the Diels-Alder reaction?

A) When the diene is electron-rich, the reaction works best when the dienophile contains one or more electron-withdrawing groups conjugated to its CC.

B) Substituents which are cis in the dienophile remain cis in the product.

C) Dienes which cannot achieve an s-cis conformation do not react in Diels-Alder reactions.

D) Secondary orbital interactions typically cause the endo product to be favored kinetically over the exo.

E) all of the above

A

E) all of the above

366
Q

137) When 1, 3-cyclopentadiene reacts with the cis-isomer of NCCH=CHCN, the major product is ________.

A) optically active

B) a meso compound

C) a racemic mixture

D) a spirocyclic compound

E) a fused bicyclic compound

A

D) a spirocyclic compound

367
Q

111) Give the major organic product for the reaction.

A
368
Q

112) Give the major organic product for the reaction.

A
369
Q

113) Give the major organic product(s) for the reaction.

A

Answer: A, B

370
Q

115) Give the major organic product(s) for the reaction.

A

Answer: D, E

371
Q

117) What is the thermodynamic product for the following reaction?

A

D) IV

372
Q

118) What is the kinetic product for the following reaction?

A

E) V

373
Q

120) What is/are the product(s) from the following reaction?

A

B) II Major, III Minor

374
Q

121) What is/are the product(s) from the following reaction?

A

C) III only

375
Q

128) What is the product of the following reaction?

A

E) V

376
Q

129) What is the product from the following reaction?

A

B) II

377
Q

130) Which of the following conjugated dienes would not react with a dieneophile in a Diels-Alder reaction?

A

E) I and III

378
Q

131) Which of the following dienes is the most reactive in a Diels-Alder reaction?

A

C) III

379
Q

132) What diene and what dieneophile would be used to synthesize the following compound?

A

B) II

380
Q

158) Give the major organic product for the reaction.

A
381
Q

159) Give the major organic product for the reaction.

A
382
Q

160) Give the major organic product for the reaction.

A

E) No reaction

383
Q

164) Which of the following is an isolated diene?

A

D) IV

384
Q

166) Give the major organic product for the reaction.

A
385
Q
  1. Which of the following is trigonal planar?
    A. boron trifluoride, BF3
    B. methyl anion, CH3-
    C. methane, CH4
    D. ammonia, NH3
A

A. boron trifluoride, BF3

386
Q
  1. Which of the following molecules is not linear?
    A. H2O
    B. CO2
    C. HCºCH
    D. Cl2
A

A. H2O

387
Q
  1. What is the approximate value of the H-C-H bond angles in methane, CH4?
    A. 90
    B. 109
    C. 120
    D. 180
A

B. 109

388
Q
  1. What is the approximate C-C-C bond angle in propene, CH3CH=CH2?
    A. 90
    B. 109
    C. 120
    D. 180
A

C. 120

389
Q
  1. What is the approximate C-C-C bond angle in propyne, HCºCCH3?
    A. 90
    B. 109
    C. 120
    D. 180
A

D. 180

390
Q
  1. What is the approximate H-C-O bond angle in formaldehyde, H2C=O?
    A. 90
    B. 109
    C. 120
    D. 180
A

C. 120

391
Q
  1. Which of the following elements has the highest electronegativity?
    A. N
    B. C
    C. O
    D. S
A

C. O

392
Q
  1. Which of the following elements has the highest electronegativity?
    A. C
    B. P
    C. Si
    D. Cl
A

D. Cl

393
Q
  1. Which of the following bonds is the most polar?
    A. F-F
    B. H-F
    C. C-H
    D. C-Si
A

B. H-F

394
Q
  1. Which of the following bonds is the most polar?
    A. O-H
    B. C-H
    C. C-C
    D. H-H
A

A. O-H

395
Q
  1. Which of the following is a polar covalent bond?
    A. Na-F
    B. C-H
    C. C-O
    D. Cl-Cl
A

C. C-O

396
Q
  1. Which of the following is a polar covalent bond?
    A. Na-Cl
    B. C-Cl
    C. C-H
    D. Cl-Cl
A

B. C-Cl

397
Q
  1. Which of the following is an ionic bond?
    A. Br-Br
    B. C-Cl
    C. C-S
    D. Na-O
A

D. Na-O

398
Q
  1. Which of the following is an ionic bond?
    A. F-F
    B. C-H
    C. Li-O
    D. C-N
A

C. Li-O

399
Q
  1. Which of the following best represents the shape of the 2s atomic orbital of carbon?
A

A. 1

400
Q
  1. Which of the following best represents the shape of a 2p atomic orbital of carbon?
A

B. 2

401
Q
  1. Which of the following best represents an sp2 hybridized atomic orbital of carbon which overlaps with the 1s atomic orbital of hydrogen to form a C-H s bonding molecular orbital in ethene, H2C=CH2
A

C. 3

402
Q
  1. Which of the following best represents an sp3 hybridized atomic orbital containing the lone pair of electrons of ammonia, NH3?
A

C. 3

407
Q
  1. Which atomic orbitals overlap to form the C=O bond of acetone, (CH3)2C=O?
    A. C 2sp3 + O 2sp2
    B. C 2sp2 + O 2p
    C. C 2sp2 + O 2sp2
    D. C 2sp3 + O 2sp
A

C. C 2sp2 + O 2sp2

408
Q
  1. Which atomic orbitals overlap to form the C-O bond of dimethyl ether, (CH3)2O?
    A. C 2sp3 + O 2sp2
    B. C 2sp2 + O 2p
    C. C 2sp2 + O 2sp2
    D. C 2sp3 + O 2sp3
A

D. C 2sp3 + O 2sp3

409
Q
  1. Which of the following statements is not true regarding resonance structures?
    A. All resonance structures must have the same number of electrons
    B. Each atom in all of the resonance structures must have a complete shell of valence electrons
    C. All resonance structures must have the same arrangement of atoms
    D. All resonance structures must be valid Lewis structures
A

B. Each atom in all of the resonance structures must have a complete shell of valence electrons

410
Q
  1. Which of the following statements is not true regarding resonance structures?
    A. Each resonance structure is in rapid equilibrium with all of the other structures
    B. The resonance structures may have different energies
    C. All resonance structures must have the same arrangement of atoms
    D. All resonance structures must have the same number of electrons
A

A. Each resonance structure is in rapid equilibrium with all of the other structures

411
Q
  1. Which of the following statements is not true about the carbonate anion, CO32-?
    A. All of the oxygen atoms bear the same amount of charge
    B. All of the carbon-oxygen bonds are the same length
    C. The carbon atom bears the negative charge
    D. It is basic
A

C. The carbon atom bears the negative charge

412
Q
  1. Which of the following statements is not true about the acetate anion, CH3CO2-?
    A. The oxygen atoms bear the same amount of charge
    B. The two carbon-oxygen bonds are the same length
    C. The carbon atom bears the negative charge
    D. It is basic
A

C. The carbon atom bears the negative charge

413
Q
  1. How many electrons are there in the valence shell of the carbon atom of a methyl cation, CH3+?
    A. 4
    B. 5
    C. 6
    D. 7
A

C. 6

414
Q
  1. How many electrons are there in the valence shell of the carbon atom of the methyl anion, CH3-?
    A. 2
    B. 4
    C. 6
    D. 8
A

D. 8

415
Q
  1. How many electrons are there in the valence shell of the oxygen atom of water?
    A. 2
    B. 4
    C. 6
    D. 8
A

D. 8

416
Q
  1. How many electrons are there in the valence shell of the nitrogen atom of ammonia?
    A. 4
    B. 5
    C. 6
    D. 8
A

D. 8

417
Q
  1. What is the approximate value of the H-C-H bond angles in a methyl cation, CH3+?
    A. 90
    B. 109
    C. 120
    D. 180
A

C. 120

418
Q
  1. What is the approximate value of the H-C-H bond angles in a methyl anion, CH3-?
    A. 90
    B. 109
    C. 120
    D. 180
A

B. 109

419
Q
  1. Which atomic orbitals overlap to form the carbon-hydrogen s bonding molecular orbitals of ethane, CH3CH3?
    A. C2p + H1s
    B. C2sp + H1s
    C. C2sp2 + H1s
    D. C2sp3 + H1s
A

D. C2sp3 + H1s

420
Q
  1. Which of the following shows curved arrows that correctly accounts for the differences between the two structures?
A

C. 3

421
Q
  1. Which atomic orbitals overlap to form the carbon-hydrogen s bonding molecular orbitals of ethene, H2C=CH2?
    A. C2p + H1s
    B. C2sp + H1s
    C. C2sp2 + H1s
    D. C2sp3 + H1s
A

C. C2sp2 + H1s

422
Q
  1. Which of the following is/are tetrahedral?
A

B. only 1 and 3

423
Q
  1. Which atomic orbitals overlap to form the carbon-carbon s and p bonding molecular orbitals of ethene, H2C=CH2?
    A. C2sp3 + C2sp3, and C2p + C2p
    B. C2sp2 + C2sp2, and C2sp2 + C2sp2
    C. C2sp2 + C2sp2, and C2p + C2p
    D. C2sp3 + C2sp3, and C2sp2 + C2sp2
A

C. C2sp2 + C2sp2, and C2p + C2p

424
Q
  1. Which atomic orbitals overlap to form the carbon-hydrogen s bonding molecular orbitals of ethyne, HCºCH?
    A. C2p + H1s
    B. C2sp + H1s
    C. C2sp2 + H1s
    D. C2sp3 + H1s
A

B. C2sp + H1s

425
Q
  1. Which atomic orbitals overlap to form the carbon-carbon s molecular bonding orbital of ethyne, HCºCH?
    A. C2p + C2p
    B. C2sp + C2sp
    C. C2sp2 + C2sp2
    D. C2sp3 + C2sp3
A

B. C2sp + C2sp

427
Q
  1. Which of the following statements is not true?
    A. The sp3C-H bond of an alkane is weaker than the spC-H bond of an alkyne.
    B. The carbon-carbon triple bond of an alkyne is shorter than the carbon-carbon bond of alkenes.
    C. The carbon-carbon triple bond of an alkene is exactly three times as strong as a carbon-carbon single bond of an alkane.
    D. The sp3C-H bond of an alkane is longer than the spC-H bond of an alkyne.
A

C. The carbon-carbon triple bond of an alkene is exactly three times as strong as a carbon-carbon single bond of an alkane.

429
Q
  1. Which of the following structures is different from the other three?
A

D. 4

430
Q
  1. Which of the following structures is different from the other three?
A

C. 3

431
Q
  1. Which of the following compounds is/are chiral?
A

A. only 1

432
Q
  1. Which of the following is the definition of a pair of enantiomers?
    A. A pair of structures that are superposable mirror images of one another
    B. A pair of stereoisomers that are non-superposable mirror images of one another
    C. A pair of stereoisomers that are not mirror images of one another
    D. A pair of stereoisomers that have equal specific rotations
A

B. A pair of stereoisomers that are non-superposable mirror images of one another

433
Q
  1. Which of the following is the definition of a pair of diastereomers?
    A. A pair of structures that are superposable mirror images of one another
    B. A pair of stereoisomers that are non-superposable mirror images of one another
    C. A pair of stereoisomers that are not mirror images of one another
    D. A pair of stereoisomers that have equal specific rotations
A

C. A pair of stereoisomers that are not mirror images of one another

434
Q
  1. Which of the following is the definition of chirality?
    A. The non-superposability of an object on its mirror image
    B. The superposability of an object on its mirror image
    C. A molecule that has a carbon atom with four different substituents
    D. A molecule with a mirror image
A

A. The non-superposability of an object on its mirror image

435
Q
  1. Which of the following is the definition of a meso compound?
    A. A molecule with stereocenter centers which is chiral
    B. A molecule with stereocenter centers which is not chiral
    C. A diastereomer with no stereocenter centers
    D. A chiral compound with more than one stereocenter center
A

B. A molecule with stereocenter centers which is not chiral

436
Q
  1. Which of the following statements is not true regarding pairs of enantiomers?
    A. They have identical melting points
    B. They have identical boiling points.
    C. They rotate plane polarized light in opposite directions
    D. They react at identical rates with chiral reagents
A

D. They react at identical rates with chiral reagents

437
Q
  1. Which of the following statements is true?
    A. All mirror images are enantiomers
    B. All molecules that have stereocenter centers are chiral
    C. Isomers that are not superposable on their mirror images are enantiomers
    D. Superposable structural isomers are enantiomers
A

C. Isomers that are not superposable on their mirror images are enantiomers

441
Q
  1. Which of the following compounds is/are chiral?
A

A. only 1

442
Q
  1. Which of the following have the S configuration?
A

C. only 1 and 2

443
Q
  1. Which of the following have the R configuration?
A

D. 1, 2 and 3

444
Q
  1. What is the configuration of the two chiral centers in the following molecule?
A

B. 3R,5S

445
Q
  1. What is the configuration of the two chiral centers in the following molecule?
A

C. 3S,5R

446
Q
  1. Which of the following Newman projections represents (2R,3R)-dibromobutane?
A

A. 1

447
Q
  1. Which of the following Newman projections represents meso-2,3-dibromobutane?
A

C. 3

448
Q
  1. Which of the following structures represent the same stereoisomer?
A

C. only 2 and 3

449
Q
  1. Which of the following structures represent the same stereoisomer?
A

C. only 2 and 3

450
Q
  1. Which of the following structures represent the same stereoisomer?
A

A. only 1 and 2

451
Q
  1. Which of the following compounds is a meso compound?
    A. (2R,3R)-dibromobutane
    B. (2R,3S)-dibromobutane
    C. (2R,3S)-3-bromo-2-butanol
    D. (2R,3R)-3-bromo-2-butanol
A

B. (2R,3S)-dibromobutane

452
Q
  1. How many stereoisomers of 2,3-dimethylbutane, (CH3)2CHCH(CH3)2, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

A. 1

453
Q
  1. How many stereoisomers of 3-chloro-2-methylbutane, (CH3)2CHCHClCH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

B. 2

454
Q
  1. How many stereoisomers of 3-bromo-2-butanol, CH3CH(OH)CHBrCH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

D. 4

455
Q
  1. How many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

C. 3

456
Q
  1. How many stereoisomers of 2,4-dimethylpentane, (CH3)2CHCH2CH(CH3)2, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

A. 1

457
Q
  1. How many stereoisomers of 4-chloro-2-methylpentane (CH3)2CHCH2CHClCH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

B. 2

458
Q
  1. How many stereoisomers of 4-bromo-2-pentanol, CH3CH(OH)CH2CHBrCH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

D. 4

459
Q
  1. How many stereoisomers of 2,4-pentanediol, CH3CH(OH)CH2CH(OH)CH3, exist?
    A. 1
    B. 2
    C. 3
    D. 4
A

C. 3

460
Q
  1. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
    A. 3
    B. 4
    C. 5
    D. 6
A

D. 6

461
Q
  1. How many isomers (constitutional and stereoisomers) exist for dimethylcyclohexane?
    A. 3
    B. 5
    C. 6
    D. 9
A

D. 9

462
Q
  1. How many isomers (constitutional and stereoisomers) exist for dimethylcyclopentane?
    A. 3
    B. 5
    C. 7
    D. 9
A

C. 7

463
Q
  1. How many isomers (constitutional and stereoisomers) exist for dimethylpentane?
    A. 2
    B. 3
    C. 4
    D. 5
A

C. 4

464
Q
  1. Which of the following statements regarding optical rotation is not true?
    A. All (+) enantiomers are dextrorotatory.
    B. All R enantiomers are dextrorotatory.
    C. All (-) enantiomers rotate plane-polarized light in a counterclockwise direction.
    D. All (+) and (-) enantiomers rotate plane-polarized light in opposite directions.
A

B. All R enantiomers are dextrorotatory.

465
Q
  1. Which of the following structures has a center of symmetry?
A

C. 3

466
Q
  1. Which of the following structures has a center of symmetry (i.e., center of inversion)?
A

C. 3

467
Q
  1. Which of the following structures have a plane of symmetry?
A

C. only 3 and 4

468
Q
  1. Which of the following structures does not have a plane of symmetry?
A

A. only 2

469
Q
  1. How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is the male hormone testosterone)?
A

C. Six

470
Q
  1. How many stereogenic centers are there in the following molecule (the naturally occurring stereoisomer is camphor, a pungent moth repellent)?
A

A. Two

471
Q
  1. Which of the following structures is chiral?
A

C. 3

472
Q
  1. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?
    A. -COOH
    B. -CHO
    C. -CH2OH
    D. -CH3
A

A. -COOH

473
Q
  1. Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?
    A. -NH2
    B. -NHCH3
    C. -CH2NH2
    D. -CH2NHCH3
A

B. -NHCH3

474
Q
  1. What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)
A

A. 3 > 4 > 2 > 1

C. 3 > 4 > 2 > 1

475
Q
  1. What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking)
A

D. 4 > 3 > 2 > 1

476
Q
  1. What is the relationship between the following pair of structures?
A

D. They are identical

477
Q
  1. What is the relationship between the following pair of structures?
A

B. They are diastereomers

478
Q
  1. What is the relationship between the following pair of structures?
A

A. They are enantiomers

479
Q
  1. How many p orbital electrons are present in furan?
    A. 4
    B. 6
    C. 7
    D. 8
A

B. 6

480
Q
  1. How many p orbital electrons are present in cyclopentadienyl anion?
    A. 4
    B. 6
    C. 7
    D. 8
A

B. 6

481
Q

1) Which of the following statements is incorrect about benzene?

A) All of the carbon atoms are sp hybridized.

B) It has delocalized electrons.

C) The carbon-carbon bond lengths are all the same.

D) The carbon-hydrogen bond lengths are all the same.

E) All twelve atoms lie in the same plane.

A

A) All of the carbon atoms are sp hybridized.

482
Q

2) Which of the following statements about benzene is correct?

A) All of the carbon atoms are sp3 hybridized.

B) It has no delocalized electrons.

C) The carbon-carbon bond length is longer than that of ethane.

D) It is a planar molecule.

E) The carbon-hydrogen bonds are not the same length.

A

D) It is a planar molecule.

483
Q

3) The delocalized π system in benzene is formed by a cyclic overlap of 6 ________ orbitals.

A) s

B) p

C) sp

D) sp2

E) sp3

A

B) p

484
Q

5) Identify the resonance hybrid.

A

D

485
Q

7) Which of the following pairs are resonance structures?

A

C) III

486
Q

8) Which of the following is not a resonance structure of the species shown?

A

D) IV

487
Q

9) In which of the following does resonance delocalization of electron density not play a role?

A) allyl cation

B) benzyl anion

C) CO32-

D) O3

E) cyclohexyl radical

A

E) cyclohexyl radical

488
Q
  1. How many constitutional isomers are there with the molecular formula C4H10?
    A. 2
    B. 3
    C. 4
    D. 5
A

A. 2

489
Q
  1. How many constitutional isomers are there with the molecular formula C5H12?
    A. 2
    B. 3
    C. 4
    D. 5
A

B. 3

490
Q
  1. How many constitutional isomers are there with the molecular formula C6H14?
    A. 3
    B. 4
    C. 5
    D. 8
A

C. 5

491
Q
  1. What is the approximate C-C-C bond angle in propane?
    A. 90
    B. 109
    C. 120
    D. 180
A

B. 109

492
Q
  1. What is the IUPAC name of the following compound?
A

B. 4-ethyl-2,2-dimethyl-heptane

493
Q
  1. What is the IUPAC name of the following compound?
A

D. 3-ethyl-5,5-dimethyl-heptane

494
Q
  1. What is the IUPAC name of the following compound?
A

C. 3-isopropyl-2,4-dimethylpentane

495
Q
  1. Which of the following compounds has 1, 2, 3 and 4 carbon atoms?
    A. hexane
    B. 2-methylhexane
    C. 2,2-dimethylhexane
    D. 2,2,3-trimethylhexane
A

D. 2,2,3-trimethylhexane

496
Q
  1. Which of the following compounds has only 1 and 3 carbon atoms?
    A. hexane
    B. 2-methylpentane
    C. 3-methylpentane
    D. 2,3-dimethylbutane
A

D. 2,3-dimethylbutane

497
Q
  1. Which of the following Newman projections does not represent 2-methylhexane?
A

C. 3

498
Q
  1. Which of the following Newman projections represents 2,4-dimethylpentane?
A

A. 1

499
Q
  1. Which of the following Newman projections represents the most stable conformation of 2,3-dimethylbutane?
A

C. 3

500
Q
  1. Which of the following Newman projections represents the most stable conformation of 2-methylbutane?
A

A. 1

501
Q
  1. Which of the following cycloalkanes has the most ring strain?
    A. cyclopropane
    B. cyclobutane
    C. cyclopentane
    D. cyclohexane
A

A. cyclopropane

502
Q
  1. Which of the following cycloalkanes has the least ring strain?
    A. cyclopropane
    B. cyclopentane
    C. cyclohexane
    D. cycloheptane
A

C. cyclohexane

503
Q
  1. Which of the following structures represents trans-1,3-dimethylcyclohexane?
A

B. 2

504
Q
  1. Which of the following structures represents trans-1,2-dimethylcyclohexane?
A

B. 2

505
Q
  1. Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane?
A

C. 3

506
Q
  1. Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane?
A

D. 4

507
Q
  1. What is the IUPAC name of the following compound?
A

B. cis-1-isopropyl-4-methylcyclohexane

508
Q
  1. What is the IUPAC name of the following compound?
A

C. trans-1-tert-butyl-2-methylcyclopentane

509
Q
  1. Which one of the following structures represents a different compound from the other three?
A

D. 4

510
Q
  1. Which one of the following structures represents a different compound from the other three?
A

C. 3

511
Q
  1. In which of the following compounds are all of the carbon atoms in the same plane?
    A. cyclopropane
    B. cyclobutane
    C. cyclopentane
    D. cyclohexane
A

A. cyclopropane

512
Q
  1. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?
    A. 1,1-dimethylcyclohexane
    B. cis-1,2-dimethylcyclohexane
    C. trans-1,2-dimethylcyclohexane
    D. cis-1,3-dimethylcyclohexane
A

C. trans-1,2-dimethylcyclohexane

513
Q
  1. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?
    A. cis-1,2-dimethylcyclohexane
    B. cis-1,3-dimethylcyclohexane
    C. trans-1,3-dimethylcyclohexane
    D. cis-1,4-dimethylcyclohexane
A

B. cis-1,3-dimethylcyclohexane

514
Q
  1. Which of the following statements is not true regarding the conformation of substituted cyclohexanes?
    A. ring inversion of cyclohexane between two chair conformations takes place via a boat conformation
    B. substituted cyclohexanes are destabilized by 1,3-diaxial interactions
    C. the boat conformation of cyclohexane is usually more stable than the chair conformation
    D. the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy
A

C. the boat conformation of cyclohexane is usually more stable than the chair conformation

515
Q
  1. What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-dichlorocyclohexane?
    A. 0
    B. 60
    C. 120
    D. 180
A

B. 60

516
Q
  1. What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans-1,2-dichlorocyclohexane?
    A. 0
    B. 60
    C. 120
    D. 180
A

B. 60

517
Q
  1. What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans-1,2-dichlorocyclohexane?
    A. 0
    B. 60
    C. 120
    D. 180
A

D. 180

518
Q
  1. Which of the following is not true regarding the properties of alkanes?
    A. alkanes are nonpolar
    B. alkanes burn in air to give H2O and CO2
    C. alkanes are highly miscible with water
    D. the strongest intermolecular force between alkane molecules is the van der Waals inte
A

C. alkanes are highly miscible with water

519
Q
  1. Which of the following is the correct order of decreasing basicity (stronger base > weaker base)?
    A. NH3 > MeNH2 > H2O > HF
    B. MeNH2 > NH3 > MeOH > CH4
    C. NH3 > Me3N > H2O > MeOH
    D. CH3COONa > NaOH > NaOMe > NaNMe2
A

B. MeNH2 > NH3 > MeOH > CH4

520
Q
  1. Which of the following is the strongest acid?
    A. CH3CH3
    B. CH3NH2
    C. CH3OH
    D. CH3F
A

C. CH3OH

521
Q
  1. Which of the following is the strongest acid?
    A. HCl
    B. HI
    C. HF
    D. HBr
A

B. HI

522
Q
  1. Which of the following is easiest to deprotonate?
    A. CH4
    B. CH3CH3
    C. CH2=CH2
    D. HCºCH
A

D. HCºCH

523
Q
  1. Which of the following is the strongest acid?
    A. CH3OH
    B. CH3CHO
    C. CH3COCH3
    D. CH3COOH
A

D. CH3COOH

524
Q
  1. Which of the following is the strongest acid?
    A. CH3NH2
    B. CH3PH2
    C. CH3OH
    D. CH3SH
A

D. CH3SH

525
Q
  1. Which of the following compounds is the strongest acid?
    A. HF
    B. H2O
    C. NH3
    D. CH4
A

A. HF

526
Q
  1. Which of the following compounds is the strongest acid?
    A. CH3OCH3
    B. CH3CH2OH
    C. CH3CHO
    D. CH3CO2H
A

D. CH3CO2H

527
Q
  1. Which of the following compounds is the strongest acid?
    A. CH3COOH
    B. ClCH2COOH
    C. CH3CH2OH
    D. ClCH2CH2OH
A

B. ClCH2COOH

528
Q
  1. Which of the following compounds is the strongest acid?
    A. CH3COOH
    B. FCH2COOH
    C. ClCH2COOH
    D. BrCH2COOH
A

B. FCH2COOH

529
Q
  1. Which of the following compounds is the strongest acid?
    A. CH4
    B. CH3CH3
    C. H2C=CH2
    D. HCºCH
A

D. HCºCH

530
Q
  1. Which of the following compounds is the strongest acid?
    A. CF3OH
    B. CF3CH2 CH2OH
    C. CF3CH2 CH2 CH2OH
    D. CF3CH2 CH2 CH2CH2OH
A

A. CF3OH

531
Q
  1. Which of the following compounds is the strongest acid?
    A. CH3CH2CH2COOH
    B. CH3CH2CHClCOOH
    C. CH3CHClCH2COOH
    D. ClCH2CH2CH2COOH
A

B. CH3CH2CHClCOOH

532
Q
  1. Which of the following is the strongest base?
    A. NaOH
    B. NaCO3
    C. H2O
    D. CH3OH
A

A. NaOH

533
Q
  1. Which of the following is the strongest base?
    A. iodide anion, I-
    B. fluoride anion, F-
    C. bromide anion, Br-
    D. chloride anion, Cl-
A

B. fluoride anion, F-

534
Q
  1. Which of the following anions is the strongest base?
    A. CH3COO-
    B. HO-
    C. NH2-
    D. Cl-
A

C. NH2-

535
Q
  1. Which of the following anions is the strongest base?
    A. NH2-
    B. NH3
    C. CH3CH=N-
    D. CH3CºN
A

A. NH2-

536
Q
  1. Which of the following compounds has the highest pKa?
    A. SiH4
    B. H2S
    C. PH3
    D. HCl
A

A. SiH4

537
Q
  1. Which of the following compounds has the highest pKa?
    A. NH3
    B. H2O
    C. HCl
    D. CH4
A

D. CH4

538
Q
  1. Which of the following compounds has the lowest pKa?
    A. H2O
    B. HBr
    C. NH3
    D. CH4
A

B. HBr

539
Q
  1. Which of the following compounds has the lowest pKa?
    A. H2O
    B. H2S
    C. H2Se
    D. H2Te
A

D. H2Te

540
Q
  1. Which of the following is present in the highest concentration upon dissolution of H2SO4 in water?
    A. H2SO4
    B. H+
    C. H3O+
    D. HO-
A

C. H3O+

541
Q
  1. Which of the following is present in the highest concentration upon dissolution of acetic acid in water?
    A. OH-
    B. H3O+
    C. CH3COOH
    D. CH3COOH+
A

C. CH3COOH

542
Q
  1. Which of the following terms describes the reactivity of boron tribromide, BBr3?
    A. Brønsted-Lowry acid and Lewis acid
    B. Brønsted-Lowry base and Lewis base
    C. Lewis acid and not a Brønsted-Lowry acid
    D. Lewis base and not a Brønsted-Lowry base
A

C. Lewis acid and not a Brønsted-Lowry acid

543
Q
  1. Which of the following terms describes the reactivity of trimethylamine, (CH3)3N?
    A. Brønsted-Lowry acid and Lewis acid
    B. Brønsted-Lowry base and Lewis base
    C. Lewis acid and not a Brønsted-Lowry acid
    D. Lewis base and not a Brønsted-Lowry base
A

B. Brønsted-Lowry base and Lewis base

544
Q
  1. Which set of curved arrows accounts for the deprotonation of an acid (A-H) by a base (:B)?
A

B. 2

545
Q
  1. Which sets of curved arrows accounts for the protonation of propene with HI?
A

D. 4

546
Q
  1. Which of the following terms describes the role of ethene in the acid-base reaction shown?
A

B. Brønsted-Lowry base

547
Q
  1. Which of the following terms describes the role of ethanol in the acid-base reaction shown?
A

B. Brønsted-Lowry base

548
Q
  1. Which of the following terms describes the role of ethanol in the acid-base reaction shown?
A

A. Brønsted-Lowry acid

549
Q
  1. Which of the following terms describes the role of ethyne in the acid-base reaction shown?
A

A. Brønsted-Lowry acid

550
Q
  1. Which species is the conjugate acid in the following acid-base reaction?
A

D. 4

551
Q
  1. Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
    A. CH3COOH
    B. AlCl3
    C. H2O
    D. CH3OH
A

B. AlCl3

552
Q
  1. Which of the following is a feature of a Lewis acid?
    A. proton donor
    B. proton acceptor
    C. electron pair donor
    D. electron pair acceptor
A

D. electron pair acceptor

553
Q
  1. Which of the following is a feature of a Lewis base?
    A. proton donor
    B. proton acceptor
    C. electron pair donor
    D. electron pair acceptor
A

C. electron pair donor

554
Q
  1. Which of the following is a feature of a Brønsted-Lowry acid?
    A. proton donor
    B. proton acceptor
    C. electron pair donor
    D. electron pair acceptor
A

A. proton donor

555
Q
  1. Which of the following is a feature of a Brønsted-Lowry base?
    A. proton donor
    B. proton acceptor
    C. electron pair donor
    D. electron pair acceptor
A

B. proton acceptor

556
Q
  1. Which of the following has the highest bond dissociation energy?
    A. HF
    B. HCl
    C. HBr
    D. HI
A

A. HF

557
Q
  1. Which of the following concepts can be used to rationalize the observation that acetic acid is a stronger acid than methanol?
    A. electronegativity
    B. resonance
    C. valence shell electron pair repulsion theory
    D. Pauli exclusion principle
A

B. resonance

558
Q
  1. Which atom in the following structure is preferentially protonated by a strong acid?
A

A. i

559
Q
  1. What is the approximate pKa value of HCl?
    A. -7
    B. 5
    C. 16
    D. 51
A

A. -7

560
Q
  1. What is the approximate pKa value of acetic acid?
    A. -7
    B. 5
    C. 16
    D. 51
A

B. 5

561
Q
  1. Which of the following has a pKa value of approximately 16?
    A. HBr
    B. CH3COOH
    C. CH3CH2OH
    D. HCºCH
A

C. CH3CH2OH

562
Q
  1. Which of the following has a pKa value of approximately 25?
    A. CH3CH3
    B. CH2=CH2
    C. HCºCH
    D. CH3CH2OH
A

C. HCºCH

563
Q
  1. Which of the following statements is not true?
    A. The position of the equilibrium for an exergonic reaction favors products
    B. The products of an exergonic reaction have a higher Gibbs free energy than the reactants.
    C. The equilibrium constant of a reaction for which DG = 0 is 1.
    D. DG = DH - TDS
A

B. The products of an exergonic reaction have a higher Gibbs free energy than the reactants.

564
Q
  1. Which of the following energy diagrams represents the fastest reaction?
A

B. 2

565
Q
  1. Which of the following energy diagrams represents the slowest reaction?
A

D. 4

566
Q
  1. Which of the following is a definition of the rate-determining step of a reaction mechanism?
    A. the first step
    B. the last step
    C. the step that crosses the highest energy barrier
    D. the most exothermic step
A

C. the step that crosses the highest energy barrier

567
Q
  1. Which of the following is a definition of the activation energy of a reaction?
    A. the difference in Gibbs free energy between the reactants and the transition state
    B. the difference in Gibbs free energy between the reactants and the intermediate
    C. the difference in Gibbs free energy between the reactants and the product
    D. the difference in Gibbs free energy between the transition state and the product
A

A. the difference in Gibbs free energy between the reactants and the transition state

568
Q
  1. Which of the following energy diagrams best represents the changes in energy during addition of HBr to an alkene?
A

A. 1

569
Q
  1. What is the major organic product obtained from the following reaction?
A

A. 1

570
Q
  1. What is the major organic product obtained from the following reaction?
A

B. 2

571
Q
  1. What is the major organic product(s) obtained from the following reaction?
A

B. 2-hexyne

572
Q
  1. What is the major organic product(s) obtained from the following reaction?
A

C. 1-propene + propyne

573
Q
  1. What is(are) the major organic product(s) obtained from the following substitution reaction?
A

A. only 1

574
Q
  1. What is(are) the major organic product(s) obtained from the following substitution reaction?
A

D. a mixture of 1 and 2

575
Q
  1. Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?
A

A. 1 reacts faster than 2

576
Q
  1. What is the major elimination product obtained from the following reaction?
A

B. 2

577
Q
  1. What is the major organic product obtained from the following reaction?
A

A. 1

578
Q
  1. Which of the following is most likely to undergo rearrangement during reaction with methanol?
A

B. 2

579
Q
  1. Which of the following compounds undergoes the most rapid hydrolysis reaction?
A

B. 2

580
Q
  1. Which of the following energy diagrams represents the course of an exothermic E2 reaction?
A

C. 3

581
Q
  1. Which of the following energy diagrams represents the course of an exothermic E1 reaction?
A

A. 1

582
Q
  1. Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?
A

A. 1

583
Q
  1. Which of the following represents the transition state of the rate-determining step in the reaction between 2-chloropropane and sodium amide leading to elimination?
A

C. 3

584
Q
  1. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol leading to elimination?
A

B. 2

585
Q
  1. Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?
A

A. 1

586
Q
  1. Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?
    A. sodium methoxide
    B. sodium ethoxide
    C. sodium isoproxide
    D. sodium tert-butoxide
A

D. sodium tert-butoxide

587
Q
  1. Which of the following most favors elimination rather substitution in a reaction with sodium methoxide?
    A. bromomethane
    B. bromoethane
    C. 1-bromopropane
    D. 2-bromopropane
A

D. 2-bromopropane

588
Q
  1. What is the best choice of reagent to perform the following transformation?
A

D. KOtBu

589
Q
  1. What is the best choice of reagent to perform the following transformation?
A

A. H2SO4

590
Q
  1. What is the IUPAC name of the following compound?
A

C. (R)-3-chloro-1-methylcyclohexene

591
Q
  1. What is the IUPAC name of the following compound?
A

D. (R)-3-bromo-3-methyl-1-hexene

592
Q
  1. What is the IUPAC name of the following compound?
A

D. (Z)-2-chloro-3,4-dimethyl-2-pentene

593
Q
  1. What is the major organic product obtained from the following reaction?
A

A. 1

594
Q
  1. What is the major organic product obtained from the following reaction?
A

D. 4

595
Q
  1. Which of the following compounds is the most reactive dienophile?
A

C. 3

596
Q
  1. Which of the following is the least reactive dienophile?
A

B. 2

597
Q
  1. Which of the following is the least reactive diene in Diels Alder reactions?
A

A. 1

598
Q
  1. Which of the following is the least reactive diene in Diels Alder reactions?
A

B. 2

599
Q
  1. What is the major organic product obtained from the following reaction?
A

B. 2

600
Q
  1. What is the major organic product obtained from the following reaction?
A

B. 2

601
Q
  1. What is the major organic product obtained from the following reaction?
A

C. 3

602
Q
  1. What is the major organic product obtained from the following reaction?
A

A. 1

603
Q
  1. What is the major organic product obtained from the following reaction?
A

C. 3

604
Q
  1. What is the major organic product obtained from the following reaction?
A

A. 1

605
Q
  1. What is the major organic product obtained from the following reaction?
A

B. 2

606
Q
  1. What is the hybridization of carbon atoms labeled i - iii in the following structure?
A

C. i = sp2; ii = sp; iii = sp2

607
Q
  1. What is the IUPAC name of the following compound?
A

B. (E)-3-ethyl-5-methyl-1,4-heptadiene

608
Q
  1. Which is the correct assignment of the names of the following groups?
A

D. 1 = vinyl; 2 = allyl; 3 = phenyl

609
Q
  1. Which is the correct assignment of the names of the following groups?
A

C. 1 = methylene; 2 = phenyl; 3 = vinyl

610
Q
  1. What is the smallest trans cycloalkene that is stable at room temperature?
    A. (E) cyclohexene
    B. (E) cycloheptene
    C. (E) cyclooctene
    D. (E) cyclodecene
A

C. (E) cyclooctene

CHM 331 (9 decks)

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