Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

ORG CHEM > ORG CHEM 1 > Flashcards

ORG CHEM 1 Flashcards

You may prefer our related Brainscape-certified flashcards:
Periodic Table flashcards Chemistry 101 flashcards AP® Chemistry flashcards Organic Chemistry 101 flashcards
1
Q

How many electrons occupy the bonding molecular orbitals of a CN triple bond?

2 4 6 8

A

6

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

Which of the following species is not amphoteric ?

NH3 HF NH4(+) HCO3(-)

A

NH4(+)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

Which of the following molecules will not have a dipole moment?

CH3Cl
CH3OCH3
CH2Cl2
CCl4

A

CCl4

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

Which of the following molecules has a dipole moment?

CBr4
CH2=CH2
BF3
SO2

A

SO2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

Which of the following molecules has a linear shape?

NH3
H2S
CO2
H2CO

A

CO2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

Which of the following intermediates is pyramidal in shape?

H3C(+)
H2C:
H3C:(-)
DHC≡C:(-)

A

H3C:(-)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

In which compound does carbon have the highest oxidation state?

CH4
HCN
H2CO
CH2Cl2

A

HCN

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Which of the following statements applies to a C10H14O2 compound?

it may have 2 double bonds and 2 rings
it may have 3 double bonds and 0 rings
it may have 1 triple bond and 3 rings
it may have 0 double bonds and 3 rings

A

it may have 2 double bonds and 2 rings

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Which of the following compounds would be considered an electrophilic reagent?

NH3
Br2
CH3OH
NH2OH

A

Br2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Which of the following compounds would you expect to be most soluble in water?

CH2Cl2
C6H12 (cyclohexane)
CH3CH2OH
C2H5OC2H5

A

CH3CH2OH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

The following compounds have similar molecular weights. Which has the highest boiling point?

CH3CH=O
C2H5OH
CH3OCH3
CH3CH2CH3

A

C2H5OH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Which of the following compound pairs are constitutional isomers?

CH3CH2OCH3 and CH3CH2CHO
CH3CH2CHO and CH3CH2CH2OH
CH3COCH2CH3 and CH3CH2COCH3
CH3CH2CH2CHO and CH3COCH2CH3

A

CH3CH2CH2CHO and CH3COCH2CH3

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

Which of the following compounds may be classed as a protic solvent?

tert-butanol
diethyl ether
n-hexane
acetone

A

tert-butanol

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Which of the following is not a nucleophile?

H2O
CH3NH2
C2H5SH
C6H12 (cyclohexane)

A

C6H12 (cyclohexane)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Which of the following is not an electrophile?

C2H5OC2H5
BF3
[CH3]3C(+)
HOCl

A

C2H5OC2H5

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Which of the following compounds has a C-H bond with the lowest bond dissociation energy?

C2H6
C6H6
C2H2
CH3CH=CH2

A

CH3CH=CH2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

In order for a reagent to behave as a nucleophile it must have ..

an overall positive charge.
an overall negative charge.
a non-bonding electron pair.
a nitrogen or sulfur atom.

A

a non-bonding electron pair

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

The H–C–O bond angle in H2C=O (formaldehyde) is approximately …..

90º
109º.
120º.
180º.

A

120º.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

Which of the following molecular formulas is reasonable for a stable compound?

C8H14O2Cl
C6H14Br2
C7H10NF
C30H54N2Cl

A

C7H10NF

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

What formal charges are present in the molecule C6H5C≡N-O?
(all heavy atoms have a valence shell octet, and C6H5- is a phenyl group)

N is -1 and C is +1
N is +1 and C is -1
O is -1 and C is +1
O is -1 and N is +1

A

O is -1 and N is +1

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Which statement about members of a homologous series is true ?

they are all constitutional isomers
they are always hydrocarbons
each differs from its nearest neighbors by 14 amu
they may also be classified as tautomers

A

each differs from its nearest neighbors by 14 amu

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

are present in (CH3)3CCH2OCH3?

2
3
4
8

A

3

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

The pKas of H2CO3 are 6.4 & 10.3. The pKa of HOBr is 8.7. If equimolar amounts of Na2CO3 and HOBr are dissolved in water what will be the predominant anionic species in the resulting solution?

HCO3-1 and BrO-1
CO3-2, Br-1 and OH-1
HCO3-1 and Br-1
CO3-2 and 2 BrO-1

A

HCO3-1 and BrO-1

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

Which of the following is a conjugate base of CH3NHOH?

CH3NH-1
CH3NHO-1
CH3NH3+1
CH2=NOH-1

A

CH3NHO-1

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
Q

Which of the following series contain a free radical, a nucleophile and an electrophile?

Br- BF3 NH3
NH3 NO2+ Br2
H2O Cl· NH3
Cl2 CH4 NH3

A

Br- BF3 NH3

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
26
Q

Which of the following species has a planar molecular configuration?

SO3-2
SO3
SOCl2
SO2Cl2

A

SO3

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
27
Q

Which of the following compounds does not have a planar molecular configuration?

H2C=CH2
H2C=CH–C≡CH
H2C=C=CH2
H2C=C=C=CH2

A

H2C=C=CH2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
28
Q

How would the bond strength of the C:C double bond in an alkene compare to that of a C:C single bond in the corresponding alkane?

The double bond would have the same strength as the single bond.

The double bond would be stronger than, but less than twice as strong as the single bond.

The double bond would have exactly twice the strength of the single bond.

The double bond would have more than twice the strength of the single bond.

A

The double bond would be stronger than, but less than twice as strong as the single bond.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
29
Q

Which of the following cations is most stable?

FH2+
OH3+
NH4+
CH5+

A

NH4+

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
30
Q

The toxic environmental pollutant dioxin is 44.8% carbon, 1.25% hydrogen and 44.0% chlorine. Its molecular weight is 320±10
What is the molecular formula of dioxin?

C10H8O4Cl4
C12H6O2Cl4
C6H2OCl2
C12H4O2Cl4

A

C12H4O2Cl4

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
31
Q

Which of the following covalent compounds does not have any formally charged atoms?

(CH3)3NO
CH2=N=N
CH3-O-N=O
CH3C≡NO

A

CH3-O-N=O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
32
Q

Which of the following statements is not generally correct?

endothermic reactions have larger energies of activation than exothermic reactions

the rate of a reaction is proportional to its activation energy

the rate of a reaction generally increases as the temperature is raised

all reactions in which bonds are broken and formed have a significant activation energy

A

endothermic reactions have larger energies of activation than exothermic reactions

33
Q

Which of the following compounds has no isomer?

CH3CH2CH2Cl
CH3CHO
CH2=CHCl
ClCH2CH2Cl

A

CH2=CHCl

34
Q

Which of the following statements about carbon is not correct?

carbon forms strong covalent bonds to itself, allowing chains and rings to be made.

carbon expands its valence shell to accomodate more than eight electrons and thus forms double and triple bonds.

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.

carbon and hydrogen have similar electronegativity and form strong bonds to each other, thus avoiding the high reactivity shown by metal hydrides.

A

carbon expands its valence shell to accomodate more than eight electrons and thus forms double and triple bonds.

35
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-tetramethylpentane
A

2,4,4-trimethylhexane

36
Q

The alkane CH3CH2C(CH3)2CH2CH(CH3)2 has how many 1º, 2º. 3º & 4º carbon atoms?

1º 2º 3º 4º

4 2 2 1
5 1 2 1
5 2 1 1
6 1 1 1

A

5 2 1 1

37
Q

There are four constitutional isomers having the formula C4H9Cl. Which of the following would be a correct IUPAC name for one of these isomers?

1-chloro-2-methylpropane
3-chlorobutane
2-chloro-2-methylbutane
1-chloro-3-methylpropane

A

1-chloro-2-methylpropane

38
Q

Which isomer of hexane has only two different sets of structurally equivalent hydrogen atoms.?

2,2-dimethylbutane
2-methylpentane
3-methylpentane
2,3-dimethylbutane

A

2,3-dimethylbutane

39
Q

Limiting your answer to cycloalkanes and ignoring stereoisomers, how many C6H12 constitutional isomers are there?

6
9
11
13

A

11

40
Q

The IUPAC name for (CH3)2CHCH(CH3)CH2CH=CH2 is …

4,5-dimethyl-1-hexene
4,5,5-trimethyl-1-pentene
2,3-dimethyl-5-hexene
4-methyl-4-isopropyl-1-butene

A

4,5-dimethyl-1-hexene

41
Q

How many isomeric pentenes (C5H10) exist? (count stereoisomers as well)

4
5
6
7

A

6

42
Q

The preferred conformation of cis-1,3-dimethylcyclohexane is …

chair–diaxial
chair–diequatorial
chair–one axial / one equatorial
boat–mixed orientations

A

chair–diequatorial

43
Q

A C6H12 compound reacts with ozone to yield a single C3H6O product. Gas phase free radical bromination of the hydrocarbon gives a single C6H11Br product. A likely identification of this compound is ..

cyclohexane
cyclohexene
3-hexene
2,3-dimethyl-2-butene

A

2,3-dimethyl-2-butene

44
Q

The most typical reaction of simple alkenes is …

electrophilic substitution
nucleophilic substitution
electrophilic addition
nucleophilic addition

A

electrophilic addition

45
Q

Which of the following dimethylcyclobutanes is chiral ?

trans-1,2-dimethylcyclobutane
cis-1,2-dimethylcyclobutane
trans-1,3-dimethylcyclobutane
cis-1,3-dimethylcyclobutane

A

trans-1,2-dimethylcyclobutane

46
Q

Which of the following C6H12 isomers has the largest heat of combustion?

cyclohexane
methylcyclopentane
ethylcyclobutane
propylcyclopropane

A

propylcyclopropane

47
Q

The radical halogenation of 2-methylpropane gives two products: (CH3)2CHCH2X (minor) and (CH3)3CX (major). Chlorination gives a larger amount of the minor product than does bromination, Why?

Bromine is more reactive than chlorine and is able to attack the less reactive 3º C-H.

Bromine atoms are less reactive (more selective) than chlorine, and preferentially attack the weaker 3º C-H bond.

The methyl groups are more hindered to attack by the larger bromine atom.

Bromination is reversible and the more stable 3º-alkyl bromide is formed exclusively.

A

Bromine atoms are less reactive (more selective) than chlorine, and preferentially attack the weaker 3º C-H bond.

48
Q

A tertiary carbocation (carbonium ion) is more stable than either a secondary or primary carbocation because …
A) it carries three positive charges
B) it has a pyramidal configuration
C) it has a trigonal planar configuration
D) it possesses three electron-donating substituent groups

A

it possesses three electron-donating substituent groups

49
Q

Which of the following is not an electrophile?

C2H5OC2H5
BF3
[CH3]3C(+)
HOCl

A

C2H5OC2H5

50
Q

Which of the following olefins would you expect to react most rapidly with concentrated sulphuric acid ?

H2C=CH2
(CH3)2C=CH2
Cl2C=CCl2
CF3CH=CH2

A

(CH3)2C=CH2

51
Q

Which compound is a likely product from addition of Cl2 to 1-butene?

CH3CH2CH2CHCl2
CH3CH2CHClCH2Cl
ClCH2CH2CH2CH2Cl
CH3CH2CCl2CH3

A

CH3CH2CHClCH2Cl

52
Q

The product from OsO4 hydroxylation of trans-2-butene will be …

achiral
optically active
racemic
a meso compound

A

racemic

53
Q

The product from bromine addition to trans-2-butene will be …

optically active
racemic
a meso compound
chiral

A

a meso compound

54
Q

Addition of 1 equivalent of bromine to 2,4-hexadiene at 0º C gives 4,5-dibromo-2-hexene plus an isomer. Which of the following is that isomer?

5,5-dibromo-2-hexene
2,5-dibromo-3-hexene
2,2-dibromo-3-hexene
2,3-dibromo-4-hexene

A

2,5-dibromo-3-hexene

55
Q

How many sp hybridized carbon atoms are present in a molecule of 3-methyl-4-vinyl-1,2-heptadien-5-yne?

2
3
4
5

A

3

56
Q

Treatment of 1-methylcyclohexene with an ether solution of diborane (B2H6), followed by reaction with alkaline H2O2 produces what product?

1-methylcyclohexanol
cis-1-methylcyclohexane-1,2-diol
cis-2-methylcyclohexanol
trans-2-methylcyclohexanol

A

trans-2-methylcyclohexano

57
Q

Two C4H6 isomers give the same C4H8O product from HgSO4 catalyzed hydration in aqueous acid. However, these isomers give different C4H6Br4 products with excess bromine. What are these isomeric hydrocarbons?

cyclobutene and methylenecyclopropane
1,2-butadiene and 1,3-butadiene
1-butyne and 2-butyne
2-butyne and cyclobutene

A

1-butyne and 2-butyne

58
Q

Two C5H8 isomers undergo catalytic (Pt) hydrogenation to form the same C5H10 product. On ozonolysis followed by oxidative workup (H2O2), one isomer gave a C5H8O4 diacid, while the other isomer gave a C5H8O3 ketoacid. Which of the following isomeric pairs correspond to this evidence?

cyclopentene and 1-pentyne
cyclopentene and 1-methylcyclobutene
1-methylcyclobutene and 3-methylcyclobutene
cyclopentene and 3-methylcyclobutene

A

cyclopentene and 1-methylcyclobutene

59
Q

Considering that the angles of a regular pentagon are 108º, why is cyclopentane not planar?

all the carbons are sp2 hybridized, so there is considerable angle strain.

The C-C bonds are formed by overlap of p-orbitals, so the 90º angle results in large angle strain.

The cyclic overlap of bonding orbitals results in anti-aromaticity destabilization.

The five C-C bonds have eclipsing strain.

A

The five C-C bonds have eclipsing strain.

60
Q

Which reaction conditions would best convert 3-hexyne to cis-3-hexene?

Pt catalyst and H2.
Lindlar’s Pd catalyst and H2.
Na in liquid NH3.
NaNH2 in liquid NH3.

A

Lindlar’s Pd catalyst and H2.

61
Q

Question 81
Reaction of 1-hexene with NBS (N-bromosuccinimide) forms two isomeric bromohexenes, one of which is 3-bromo-1-hexene. Which of the following is the other isomer?

1-bromo-2-hexene.
6-bromo-1-hexene.
1-bromo-1-hexene.
2-bromo-1-hexene.

A

1-bromo-2-hexene

62
Q

A C6H10 hydrocarbon forms an insoluble silver salt when treated with silver nitrate in ethanolic ammonia. Acid catalyzed hydration with a HgSO4 catalyst generates a single C6H12O ketone, and pemanganate oxidation yields a C5H10O2 carboxylic acid. This compound is most likely which of the following?

cyclohexene.
methylenecyclopentane.
1-hexyne.
3-hexyne.

A

1-hexyne.

63
Q

Peroxide induced reaction of carbon tetrachloride with 1-butene produces which of the following?

1,1,1,3-tetrachloropentane.
1,1,1,2-tetrachloropentane.
1-chloro-2-trichloromethylbutane.
1,1-dichloro-2-ethylcyclopropane.

A

1,1,1,3-tetrachloropentane.

64
Q

Which of the following isomeric hexenes will have the smallest heat of hydrogenation?

4-methyl-1-pentene.
(E)-4-methyl-2-pentene.
(Z)-4-methyl-2-pentene.
2-methyl-2-pentene.

A

2-methyl-2-pentene.

65
Q

A C8H14 hydrocarbon (X) is reduced by sodium in liquid ammonia to a single C8H16 product (Y). Both of these compounds undergo hydrogenation (Pt catalyst) to give 2,5-dimethylhexane. Ozonolysis of Y with an oxidative workup produces a single C4H8O2 carboxylic acid. Reaction of Y with perbenzoic acid (C6H5CO3H) gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product
What are X and Y?

X is 2,5-dimethyl-3-hexyne ; Y is cis-2,5-dimethyl-3-hexene.

X is 2,5-dimethyl-3-hexyne ; Y is trans-2,5-dimethyl-3-hexene.

X is 2.5-dimethyl-1,5-hexadiene ; Y is 2,5-dimethyl-3-hexyne.

X is 2,5-dimethyl-2,4-hexadiene ; Y is cis-2,5-dimethyl-3-hexene.

A

X is 2,5-dimethyl-3-hexyne ; Y is trans-2,5-dimethyl-3-hexene.

66
Q

What reagent(s) would best achieve conversion of 3,3-dimethyl-1-butyne to the aldehyde (CH3)3CCH2CHO?

H3O(+) and catalytic Hg(+2)

(i) R2BH in ether ( R=C5H11 )
(ii) H2O2 and aqueous NaOH

KMnO4 in aqueous NaOH

(i) HOBr
(ii) aqueous NaOH

A

(i) R2BH in ether ( R=C5H11

67
Q

Reaction of 1,1-dibromopentane with three equivalents of NaNH2 in ether is followed by treatment with 0.1M HCl at 0ºC. What is the product?

cyclopentene.
1,2-pentadiene.
2-pentyne.
1-pentyne.

A

1-pentyne.

68
Q

Which of the following reagents and conditions would best serve to convert 1-butyne to 1,1-dibromobutane?

2 equivalents of HBr, no peroxides.
2 equivalents of HBr, with peroxides.
1 equivalent of Br2.
2 equivalents of Br2 followed by i equivalent of KOH.

A

2 equivalents of HBr, with peroxides.

69
Q

What is the relative rate of addition of HBr to I: 1,3-pentadiene; II: 1,4-pentadiene; and III: 1-pentyne?

I > II > III.
III > II > I.
II > I > III.
III > I > II.

A

I > II > III.

70
Q

A chiral C6H12 hydrocarbon undergoes catalytic hydrogenation to yield an achiral C6H14 product. What is the starting compound?

cis-2-hexene
3-methyl-2-pentene
4-methyl-2-pentene
3-methyl-1-pentene

A

3-methyl-1-pentene

71
Q

Reaction of 3,3,6,6-tetramethyl-1,4-cyclohexadiene, first with excess aqueous mercuric acetate, then followed by sodium borohydride reduction, produces a mixture of isomeric C10H20O2 alcohols. Excluding enantiomers, how many isomeric products may be formed in this reaction?

2
4
6
8

A

4

72
Q

Which of the following reactions of cyclohexene may be considered an oxidation?

addition of hydrogen (Pt catalyst) to give cyclohexane.

addition of HBr to give bromocyclohexane

epoxidation by perbenzoic acid to give cyclohexene oxide

mercuric acetate catalyzed hydration to give cyclohexanol

A

epoxidation by perbenzoic acid to give cyclohexene oxide

73
Q

What structural change takes place when an alkene undergoes a Simmons-Smith reaction?

addition of ethene gives a cyclobutane derivative.

the double bond is shifted to a more substituted location.

the double bond is converted to a triple bond.

a methylene group is added to give a cyclopropane derivative.

A

a methylene group is added to give a cyclopropane derivative.

74
Q

Which one of the following compounds contains the greatest number of sp2 hybridized carbon atoms?

1,4-Cycloheptadiene
2,5-dimethyl-2,3,4-hexatriene
Phenylacetylene
1,1-diallyl-3,3-divinylcyclobutane

A

1,1-diallyl-3,3-divinylcyclobutane

75
Q

Which one of the following compounds contains the greatest number of sp hybridized carbon atoms?

1,4-Cyclooctadiene
2,5-dimethyl-2,3,4-hexatriene
Phenylacetylene
1,1-diallyl-3,3-divinylcyclobutane

A

2,5-dimethyl-2,3,4-hexatriene

76
Q

Which one of the following compounds contains the greatest number of sp3 hybridized carbon atoms?

1,4-Cyclooctadiene
2,5-dimethyl-2,3,4-hexatriene
Phenylacetylene
1,1-diallyl-3,3-divinylcyclobutane

A

Phenylacetylene

77
Q

Which of the following isomers has the lowest heat of combustion?

cis-1,2-dimethylcyclohexane
trans-1,2-dimethylcyclohexane
cis-1,3-dimethylcyclohexane
trans-1,3-dimethylcyclohexane

A

cis-1,3-dimethylcyclohexane

78
Q

Compound Z, C8H14, reacts with excess hydrogen and a Pt catalyst to give 2,5-dimethylhexane as the only product. Z diplays three 13C NMR signals, all at higher field than 100 ppm, and does not absorb in the UV at wavelengths greater than 200 nm. Oxidation of Z by either ozone or potassium permanganate produces a single C4H8O2 carboxylic acid. Deduce the structure of Z.

2,5-dimethyl-3-hexyne
trans-2,5-dimethyl-3-hexene
cis-2,5-dimethyl-3-hexene
2,5-dimethyl-2,4-hexadiene

A

2,5-dimethyl-3-hexyne

79
Q

END

A

END

ORG CHEM (4 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions