Question 1

1) Which of the following best describes the carbon-chlorine bond of an alkyl chloride?    A) nonpolar; no dipole  B) polar; d+ at carbon and d- at chlorine  C) polar; d- at carbon and d+ at chlorine  D) ionic  E) none of the above

Accepted Answer

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

Question 2

2) Which of the following is classified as a vinylic halide?    A) CH3CHCHOH  B) CH3CHCHCl  C) CH3CHCHCH2Cl  D) CH3CH2CH2CH2Br  E) BrCH2CHCH2

Accepted Answer

B) CH3CHCHCl

Question 3

3) The flame retardant below has been found to be an androgen agonist and may have a contribution to an increasing rate of occurrence of prostate cancer (J. Med. Chem. 2006, 7366). What is the correct term that describes the relative position of the bromides in this structure?     A) geminal  B) vinyl  C) vicinal  D) aryl

Accepted Answer

C) vicinal

Question 4

4) What general classification is given to the molecule below?       A) primary chloride  B) secondary chloride  C) tertiary chloride  D) vinyl chloride  E) benzyl chloride

Accepted Answer

C) tertiary chloride

Question 5

11) Which of the following is a secondary halide?  A) ClCH2CH2C(CH3)3  B) ClCH2CH2CH(CH3)2  C) (CH3)2CClCH2CH3  D) (CH3)3CCHClCH3  E) ClCH2C(CH3)CH2CH3

Accepted Answer

D) (CH3)3CCHClCH3

Question 6

12) Which of the following is a tertiary halide?  A) ClCH2CH2C(CH3)3  B) ClCH2CH2CH(CH3)2  C) (CH3)2CClCH2CH3  D) (CH3)3CCHClCH3  E) ClCH2C(CH3)CH2CH3

Accepted Answer

C) (CH3)2CClCH2CH3

Question 7

13) Which of the following is a geminal dihalide?  A) cis-1,2-dibromocyclopentane   B) 3,3-dichloropentane  C) trans-1,4-diiodocyclohexane  D) isobutyl chloride  E) 1,3-dibromoheptane

Accepted Answer

B) 3,3-dichloropentane

Question 8

14) Which of the following is a vicinal dihalide?  A) cis-1,2-dibromocyclopentane  B) 3,3-dichloropentane  C) trans-1,4-diiodocyclohexane  D) isobutyl chloride  E) 1,3-dibromoheptane

Accepted Answer

A) cis-1,2-dibromocyclopentane

Question 9

15) Which of the following is a secondary alkyl halide?  A) methyl bromide  B) isopropyl chloride  C) t-butyl iodide  D) propyl bromide  E) isobutyl chloride

Accepted Answer

B) isopropyl chloride

Question 10

16) Which of the following is a primary alkyl halide?  A) methyl bromide  B) isopropyl bromide  C) t-butyl iodide  D) cyclohexyl bromide  E) isobutyl chloride

Accepted Answer

E) isobutyl chloride

Question 11

17) What is the IUPAC name of the compound shown below?     A) (1S,3S)-1,3-dichloro-1-ethyl-3-methylcyclopentane    B) (1R,3S)-1,3-dichloro-1-methyl-3-ethylcyclopentane    C) (1R,4S)-1,4-dichloro-1-ethyl-4-methylcyclopentane    D) (1R,3S)-1,3-dichloro-1-ethyl-3-methylcyclopentane    E) (1S,3R)-1,3-dichloro-3-ethyl-1-methylcyclopentane

Accepted Answer

D) (1R,3S)-1,3-dichloro-1-ethyl-

Question 12

18) What is the IUPAC name of the compound shown below?       A) (2R,3S,4S)-2-chloro-3,4-dibromo-3-methylhexane    B) (2R,3S,4S)-3,4-dibromo-2-chloro-3-methylhexane    C) (3S,4S,5S)-3,4-dibromo-5-chloro-4-methylhexane    D) (2R,3R,4S)-3,4-dibromo-2-chloro-3-methylhexane    E) (2R,3S,4R)-3,4-dibromo-2-chloro-3-methylhexane

Accepted Answer

B) (2R,3S,4S)-3,4-dibromo-2-chloro-3-methylhexane

Question 13

25) Which of the following best describes DDT?    A) a chlorocarbon used to decaffeinate coffee beans  B) a polybrominated organic compound used as a herbicide  C) a Freon used as a foaming agent  D) a mixed alkyl halide used as an anesthetic  E) a polychlorinated organic compound used as an insecticide

Accepted Answer

E) a polychlorinated organic compound used as an insecticide

Question 14

26) Which of the following alkyl halides has the smallest molecular dipole moment?  A) CH3F  B) CH3Cl  C) CH2I2  D) CH2Cl2  E) CF4

Accepted Answer

E) CF4

Question 15

28) Among the following alkyl halides, choose the one with the lowest boiling point.    A) t-butyl chloride  B) n-butyl chloride  C) t-butyl bromide  D) n-butyl iodide  E) t-butyl iodide

Accepted Answer

A) t-butyl chloride

Question 16

31) When 2,2-dimethylbutane is subjected to free-radical chlorination, ________ distinct monochlorinated products are possible and ________ of these contain asymmetric carbon atoms.    A) 4, 2  B) 5, 0  C) 3, 0  D) 5, 2  E) 4, 0

Accepted Answer

A) 4, 2

Question 17

38) What type of intermediate is present in the SN2 reaction of cyanide with bromoethane?    A) carbocation  B) free radical  C) carbene  D) carbanion  E) This reaction has no intermediate.

Accepted Answer

E) This reaction has no intermediate.

Question 18

43) Which of the following species is the least nucleophilic?    A) H2O  B) BF3  C) (CH3)3N  D) CH3O-  E) CN-

Accepted Answer

B) BF3

Question 19

44) Which of the following compounds is the most nucleophilic?    A) CH3SH  B) CH3OH  C) H2O  D) CH3CO2H  E) BF3

Accepted Answer

A) CH3SH

Question 20

50) Which of the following factors is favorable for nucleophilicity but not basicity?    A) highly polarizable  B) low electronegativity  C) negatively charged  D) sterically hindered

Accepted Answer

A) highly polarizable

Question 21

51) Which of the following solvents could be described as polar and protic?    A) ethanol  B) acetonitrile  C) dimethylformamide  D) acetone  E) 18-crown-6

Accepted Answer

A) ethanol

Question 22

53) Which of the following compounds will undergo an SN2 reaction most readily?    A) (CH3)3CCH2I  B) (CH3)3CCl  C) (CH3)2CHI  D) (CH3)2CHCH2CH2CH2I  E) (CH3)2CHCH2CH2CH2Cl

Accepted Answer

D) (CH3)2CHCH2CH2CH2I

Question 23

54) Which of the following alkyl chlorides will undergo SN2 reaction most readily?    A) 1-chloro-4-methylpentane  B) 2-chloro-4-methylpentane  C) 2-chloro-3-methylpentane  D) 3-chloro-2-methylpentane  E) 2-chloro-2-methylpentane

Accepted Answer

A) 1-chloro-4-methylpentane

Question 24

62) Which of the following statements describe a favorable attribute of a leaving group?  (More than one answer is possible.)    A) The leaving group should be highly polarizable.  B) The lower the electronegativity of the leaving group the better.  C) Good leaving groups need to have low steric hindrance.  D) The departed leaving group should have low basicity.

Accepted Answer

A) The leaving group should be highly polarizable.    D) The departed leaving group should have low basicity.

Question 25

63) Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN?    A) 1-iodohexane  B) 1-fluorohexane  C) (R)-2-bromohexane  D) iodocyclohexane  E) 1-iodo-1-methylcyclohexane

Accepted Answer

A) 1-iodohexane

Question 26

71) 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

Accepted Answer

E) 3-iodo-3-methylpentane

Question 27

72) Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?    A) PhCHBrCH3  B) (CH3)2CHCH2CH2Br  C) (CH3)2CHCH2CHBrCH3  D) CH3CH2CH2CH2Br  E) PhBr

Accepted Answer

A) PhCHBrCH3

Question 28

79) Which of the following alkyl halides reacts most rapidly via an SN1 solvolysis reaction in hot methanol?    A) 1-iodohexane  B) 1-fluorohexane  C) (R)-2-bromohexane  D) iodocyclohexane  E) 1-iodo-1-methylcyclohexane

Accepted Answer

E) 1-iodo-1-methylcyclohexane

Question 29

80) Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting).     A) 3 < 2 < 4 < 5 < 1  B) 2 < 3 < 4 < 1 < 5  C) 5 < 4 < 3 < 2 < 1  D) 2 < 3 < 4 < 5 < 1  E) 1 < 2 < 5 < 4 < 3

Accepted Answer

B) 2 < 3 < 4 < 1 < 5

Question 30

83) When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:    A) achiral.  B) chiral.  C) racemic.  D) optically active.  E) none of the above

Accepted Answer

A) achiral.

Question 31

84) When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.    A) a single, chiral compound  B) a mixture of diasteromeric ethers  C) a mixture of diasteromeric alcohols  D) a single, chiral alcohol  E) a single, chiral ether

Accepted Answer

B) a mixture of diasteromeric ethers

Question 32

86) 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 then inversion at the center undergoing substitution.    D) complete inversion at the center undergoing substitution.    E) complete retention at the center undergoing substitution.

Accepted Answer

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

Question 33

88) Which of the cations below would be subject to a structural rearrangement?         A) 1  B) 3  C) 1, 2, & 3  D) 2 & 3

Accepted Answer

B) 3

Question 34

89) Which of the following alkyl halides is most likely to undergo rearrangement in an SN1 reaction?    A) 3-bromopentane  B) 2-chloro-3,3-dimethylpentane  C) 3-chloropentane  D) bromocyclohexane  E) 1-bromo-4-methylcyclohexane

Accepted Answer

B) 2-chloro-3,3-dimethylpentane

Question 35

90) Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?    A) 2-chloro-4-methylpentane  B) 2-chloro-3-methylpentane  C) 2-chloro-2-methylpentane  D) cis-1-chloro-2-ethylcyclohexane  E) trans-1-chloro-2-ethylcyclohexane

Accepted Answer

C) 2-chloro-2-methylpentane

Question 36

91) A sample of 1-chloro-1-phenylethane with an [?]25D of -94.8? is reacted with NH3 in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [?]25D of -8.6?. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0? and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3?, which of the following statements best describes this reaction?     A) Net inversion 25% with 75% racemization -- SN1 mechanism  B) Net inversion 12% with 88% racemization -- SN1 mechanism  C) Net inversion 75% with 25% racemization -- SN2 mechanism  D) Net inversion 12% with 88% racemization -- SN2 mechanism  E) Net inversion 88% with 12% racemization -- SN2 mechanism

Accepted Answer

A) Net inversion 25% with 75% racemization -- SN1 mechanism

Question 37

95) Which of the following statements correctly describe(s) E1 reactions of alkyl halides (RX)?    I. Rate = k[base]   II. Rate = k[base][RX]  III. Rate = k[RX]  IV. The reactions occur in two or more distinct steps.  V. Rearrangements are sometimes seen.  A) II and IV  B) III and V  C) I, IV, and V  D) I only  E) III, IV, and V

Accepted Answer

E) III, IV, and V

Question 38

100) Dehydration of 1-butanol with concentrated sulfuric acid at 140?C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?    A) The reaction undergoes an E2-type elimination mechanism.  B) The reaction follows a new mechanism involving the formation of a carbanion intermediate.  C) The reaction undergoes an E1-type elimination mechanism in conjunction with a hydride shift.  D) The reaction undergoes an E2-type elimination mechanism in conjunction with a methyl shift.  E) The reaction undergoes an E1-type elimination mechanism with no shifting.

Accepted Answer

C) The reaction undergoes an E1-type elimination mechanism in conjunction with a hydride shift.

Question 39

101) How many distinct alkene products are possible when the alkyl iodide below undergoes E2 elimination?       A) 1  B) 2  C) 3  D) 4  E) 5

Accepted Answer

E) 5

Question 40

102) Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?    A) 2-chloro-2-methylpentane  B) 3-chloro-3-ethylpentane  C) 3-chloro-2-methylpentane  D) 2-chloro-4-methylpentane  E) 2-chloro-3-ethylpentane

Accepted Answer

B) 3-chloro-3-ethylpentane

Question 41

103) How many distinct alkene products results when 1-bromo-1-ethylcyclopentane is treated with NaOCH3?  A) 1  B) 2  C) 3  D) 4

Accepted Answer

B) 2

Question 42

118) When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed  two by substitution and two by elimination.        Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product?       A) KOH, ethanol and heat  B) water/acetone and heat  C) tert-butoxide/tert-butyl alcohol  D) tert-butyl alcohol and heat  E) methoxide/methanol

Accepted Answer

C) tert-butoxide/tert-butyl alcohol

Question 43

123) Which of the following mechanisms (SN1, SN2, E1, E2) feature(s) a carbocation intermediate?    A) SN1 only  B) SN2 only  C) E1 only  D) E2 only  E) both SN1 and E1

Accepted Answer

E) both SN1 and E1

Question 44

124) In which of the following mechanisms (SN1, SN2, E1, E2) are alkenes the major reaction products?    A) SN1 only  B) SN2 only  C) E1 only  D) E2 only  E) both E1 and E2

Accepted Answer

E) both E1 and E2

Question 45

125) Predict the most likely mechanism for the reaction shown below.       A) SN1  B) SN2  C) E1  D) E2  E) E1cb

Accepted Answer

A) SN1

Question 46

126) Predict the most likely mechanism for the reaction shown below.       A) SN1  B) SN2  C) E1  D) E2  E) E1cb

Accepted Answer

D) E2

Question 47

127) Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.    A) SN2 and SN1  B) E1 and E2  C) SN2 and E2  D) E1 and SN1  E) E2 and SN1

Accepted Answer

C) SN2 and E2

Question 48

128) Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.    A) SN2 and SN1  B) E1 and E2  C) SN2 and E2  D) E1 and SN1  E) E2 and SN1

Accepted Answer

D) E1 and SN1

Question 49

129) The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?    A) SN1  B) SN2  C) E1  D) E2  E) E1cb

Accepted Answer

D) E2

Question 50

130) The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?  A) SN1  B) SN2  C) E1  D) E2  E) E1cb

Accepted Answer

A) SN1

Question 51

131) When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ________ that is generated through an ________ mechanism.  A) ether, SN1  B) ether, SN2  C) ether, E1  D) alkene, E2  E) alkene, E1

Accepted Answer

D) alkene, E2

Question 52

132) When 3-iodo-3-ethylpentane is heated in methanol, the major organic product is an ________ that is generated through an ________ mechanism.    A) ether, SN1  B) ether, SN2  C) ether, E1  D) alkene, E2  E) alcohol, E1

Accepted Answer

A) ether, SN1

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