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OrgChem Flashcards

1
Q

Which of the following statements about carbon is NOT correct?
A. Carbon forms strong covalent bonds to itself, allowing chains and rings to be made.
B. Carbon expands its valence shell to accommodate more than eight electrons and thus forms double and triple bonds.
C. Carbon and hydrogen have similar electronegativity and form strong bonds to each other, thus avoiding the high reactivity shown by metal hydrides.
D. Carbon forms strong covalent bonds to elements like nitrogen and oxygen because it does not have lone pairs of valence electrons to destabilize the bonds.

A

B

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2
Q

Which statement about bonding is TRUE?
A. A pi bond is as twice as strong as a sigma bond
B. A double bond consists of two pi bonds.
C. A sigma bond has cylindrical symmetry about the bonding axis.
D. A sigma bond results from the sideways overlap of hybridized orbitals.

A

C

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3
Q

How many sigma and pi bonds are in acetylene?
A. 2 sigma, 2 pi
B. 3 sigma, 2 pi
C. 2 sigma, 3 pi
D. 3 sigma, 3 pi

A

B

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4
Q

What is the bond angle and molecular geometry around C in CH2=CH2?
A. 120°, tetrahedral
B. 109.5°, tetrahedral
C. 120°, planar
D. 109.5°, planar

A

C

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5
Q

What is the hybridization of O in CH3OH?
A. sp3
B. sp2
C. sp
D. sp3d

A

A

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6
Q

Which of the following orbitals provide the most efficient overlap?
A. s-s
B. sp3-sp3
C. sp-sp
D. p-p

A

C

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7
Q

What is the IUPAC name for CH3CH2C(CH3)2CH2CH(CH3)2?
A. 3,3,5-trimethylhexane
B. 2,2,5-trimethylhexane
C. 2,4,4-trimethylhexane
D. 1,1,3,3-tetramethy|pentane

A

C

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8
Q

What is the IUPAC name of (CH3)2CHCH=CHCH3?
A. 1,2-methyl-isopropylethene
B. 1,1-dimethyl-2-butene
C. 1-isopropyipropene
D. 4-methyl-2-pentene

A

D

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9
Q

How many constitutional isomers are possible for the molecular formula C5H12?
A. 1
B. 2
C. 3
D. 4

A

C

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10
Q

How many distinct branched alkanes are there with the formula C6H14?
A. 1
B. 2
C. 3
D. 4

A

D

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11
Q

Which of the following is TRUE for an optically active compound?
A. The molecular configuration is chiral.
B. The molecular configuration is achiral.
C. The compound is a racemic mixture of enantiomers.
D. The molecular configuration must have two or more stereogenic centers.

A

A

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12
Q

Compounds which have different arrangements of atoms in space while having same atoms bonded to each other are
A. constitutional isomers
B. functional group isomers
C. coordination isomers
D. stereoisomers

A

D

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13
Q

Which of the following statements describes enantiomers?
A. They are achiral stereoisomers.
B. They are stereoisomers having a mirror plane of symmetry.
C. They are stereoisomers having non-identical mirror image configurations.
D. They are stereoisomers that do not have non-identical mirror image configurations.

A

C

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14
Q

Which substance can exist in enantiomeric forms?
А. 3-methylpentane
B. 2-methylpentane
C. 3-methyl-1-butanol
D. 2-methyl-1-butanol

A

D

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15
Q

A racemic mixture consists of equal quantities of
A. cis-trans isomers
B. diastereomers
C. enantiomers
D. structural isomers

A

C

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16
Q

Which of the following is NOT an addition reaction?
A. Hydration
B. Dehydration
C. Halogenation
D. Hydrohalogenation

A

B

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17
Q

An this type of reaction, one sigma bond breaks and another forms at the same carbon atom.
A. Addition
B. Elimination
C. Substitution
D. Rearrangement

A

C

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18
Q

During symmetrical bond breaking, ______ form
A. Radicals
B. Electrophiles
C. Nucleophiles
D. None of the above

A

A

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19
Q

All of the following are electrophiles EXCEPT
A. Br+
B. BF3
C. AICl3
D. NH3

A

D

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20
Q

Which of the following statements is FALSE?
A. It is not necessary for a nucleophile to have an unshared electron pair.
B. A species can react as an electrophile if it contains an atom (other than hydrogen) with an incomplete valence octet.
C. A species can react as an electrophile, even if it has one or more unshared electron pairs.
D. Any species bearing a lone pair can normally react as a nucleophile.

A

A

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21
Q

Liquified petroleum gas is mainly composed of
A. Methane and Ethane
B. Ethane and Propane
C. Propane and Butane
D. Butane and Hexane

A

C

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22
Q

The hydrocarbon having the lowest boiling point is
A. CH4
B. C2H4
C. C4H10
D. C6H6

A

A

23
Q

Compared to ionic compounds of similar molar mass, hydrocarbons typically have
I. Higher water solubility
II. Higher melting points

A. I only
B. II only
C. both I and Il
D. neither I nor lI

A

D

24
Q

Which class of compounds consist exclusively of saturated hydrocarbons?
A. Alkenes
B. Aromatics
C. Alkynes
D. Alkanes

A

D

25
Q

Alkanes undergo halogenation via
A. free radical substitution
B. electrophilic substitution
C. electrophilic addition
D. nucleophilic addition

A

A

26
Q

Alkenes and alkynes, because they contain pi bonds, undergo this type of reaction.
A. Electrophilic addition
C. Electrophilic substitution
B. Nucleophilic addition
D. Nucleophilic substitution

A

A

27
Q

Which of the following reactions can reduce an alkene yielding an alkane?
A. Oxidation
B. Bromination
C. Hydrogenation
D. Polymerization

A

C

28
Q

Which of the following is produced from addition of Cl to 1-butene?
A. CH3CH2CClСН3
B. CH3CH2CH2CHCl2
C. CH3CH2CHClCH2Cl
D. ClCH2CH2CH2Cl

A

C

29
Q

All of the following reactions convert alkenes to alcohols EXCEPT
A. halohydrin formation
B. ozonolysis
C. hydroboration-oxidation
D. oxymercuration-demercuration

A

B

30
Q

What is the position of the bromine atom relative to the methyl group in 3-bromotoluene?
A. meta
B. para
C. ortho
D. trans

A

A

31
Q

Aromatic compounds undergo substitution reactions instead of addition reactions because
A. the benzene ring is electron rich.
B. the hydrogens of benzene are relatively loosely bound.
C. the benzene ring is sterically crowded hence only substitution can occur.
D. the integrity of the benzene ring and the stable aromatic ir system remains intact.

A

D

32
Q

Which of the following substituents is NOT an ortho, para directing group in EAS?
A. -Cl
в. -OH
C. -NO2
D. -CH3

A

C

33
Q

AlCl3 is a catalyst used in the alkylation and acylation of aromatic compounds. It is a(an).
A. Arrhenius acid
B. Bronsted-Lowry acid
C. Lewis acid
D. Lewis base

A

C

34
Q

What is the product from the Friedel-Crafts alkylation of nitrobenzene?
A. ortho-nitrotoluene
B. meta-nitrotoluene
C. para-nitrotoluene
D. ortho-nitrotoluene and para-nitrotoluene

A

B

35
Q

Freon is an example of a(an)
A. hydrocarbon
B. alkyl halide
C. alcohol
D. aldehyde

A

B

36
Q

What is the role of hydroxide ion in the reaction below?
СН3CH2CH2CH2Br + ОН- → СН3CH2CH2CH2OH + Вr-
A. Lewis acid
B. Electrophile
C. Nucleophile
D. Oxidizing agent

A

C

37
Q

Which alkyl halide will most likely react via SN2 mechanism?
A. bromobenzene
B. bromomethane
C. 2-bromo-2-methylpropane
D. 1-bromobutane

A

B

38
Q

Which chloroalkane undergoes substitution with OH- exclusively by an SN1 mechanism?
А. (СН3)3ССІ
B. (CH3)2CHCH2Cl
C. CH3CH2CHClCH3
D. CH3CH2CH2CH2Cl

A

A

39
Q

Among the following group of compounds, which will have the highest boiling point?
A. alkenes
B. alkynes
C. alcohols
D. haloalkanes

A

C

40
Q

An industrial source of alcohol.
A. coal
B. fats
C. sugar
D. ether

A

C

41
Q

Which of the following will react faster with HBr?
A. 1-butanol
B. 2-butanol
C. 2-methyl-1-propanol
D. 2-methyl-2-propanol

A

D

42
Q

Dehydration of an alcohol yields a(an)
A. alkene
B. alkyne
C. aldehyde
D. ketone

A

A

43
Q

Which of the following can react with NaOH?
A. phenol
B. ethanol
C. ethylene
D. diethyl ether

A

D

44
Q

Which of the following is arranged in order of increasing boiling point?
A. 2-methylbutane < n-pentane < butanone < butanol
B. n-pentane < 2-methylbutane < butanone < butanol)
C. 2-methylbutane < n-pentane < butanol < butanone
D. n-pentane < 2-methylbutane < butanol < butanone

A

A

45
Q

Methanal is used as
A. fuel
B. antiseptic
C. preservative
D. refrigerant

A

B

46
Q

The simplest ketone is
A. acetone
B. lactone
C. cyclohexanone
D. ethyl methyl ketone

A

A

47
Q

Carbonyl compounds undergo this type of reaction.
A. Electrophilic addition
B. Nucleophilic addition
C. Electrophilic substitution
D. Nucleophilic substitution

A

B

48
Q

Which compounds react readily with acidic dichromate solution (K2Cr2O7 in aqueous H2SO4)? An alcohol or aldehyde?
A. Alcohol only
B. Aldehyde only
C. Both
D. Neither

A

A

49
Q

Ketones react with reducing agents to form _______
A. phenols
B. primary alcohols
C. secondary alcohols
D. tertiary alcohols

A

C

50
Q

Which of the following will have the highest boiling point?
A. butane (58 g/mol)
B. propanal (58 g/mol)
C. 1-butanol (60 g/mol)
D. acetic acid (60 g/mol)

A

D

51
Q

Carboxylic acids are more acidic than alcohols because
A. of the increased polarity of the O-H due to the carbonyl group.
B. of the stability of the carboxylate anion formed upon ionization.
C. of the higher Ka value.
D. All of the above.

A

D

52
Q

What is formed when an alcohol reacts with a carboxylic acid with an acid catalyst?
A. anhydride
B. acid chloride
C. ester
D. ether

A

C

53
Q

Which of the following will react most rapidly with water?
A. Nitrile
B. —Cl
C. —NH2
D. —OCH3

A

B

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