Deck 8: Substitution Reactions of Alkyl Halides

Question 1

Which of the following S_N2 reactions is the slowest?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHBrCH } _ { 3 } + \mathrm { OH } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHOHCH } _ { 3 } + \mathrm { Br } ^ { - }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHBrCH } _ { 3 } + \mathrm { H } _ { 2 } \mathrm { O } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHOHCH } _ { 3 } + \mathrm { HBr }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \mathrm { OH } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { Br } ^ { - }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \mathrm { H } _ { 2 } \mathrm { O } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { HBr }$

Answer 1

$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHBrCH } _ { 3 } + \mathrm { H } _ { 2 } \mathrm { O } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHOHCH } _ { 3 } + \mathrm { HBr }$

Question 2

Which of the following is a secondary alkyl halide?

A)CH₃Br
B) (CH₃)₃CBr
C) (CH₃)₂CHBr
D)(CH₃)₂CHCH₂Br

Answer 2

(CH₃)₂CHBr

Question 3

When (S)-2-bromobutane undergoes an SN2 , the product is the compound shown below. What is the configuration of the product?

A) S only
B) R only
C) both R and S with more R than S
D) both R and S with more S than R
E) equal amounts of R and S

Answer 3

R only

Question 4

Which of the following alkyl halides reacts the fastest in an SN2 reaction?

A) 1-chloropropane
B) 1-bromopropane
C) 1-fluoropropane
D) 1-iodopropane

Question 5

What is the nucleophile in the following reaction?
I.


II. $\mathrm { H } _ { 2 } \mathrm { O }$

III. $\mathrm { H } _ { 3 } \mathrm { O } ^ { \oplus }$

IV. $\mathrm { I } ^ { \ominus }$

V. $\mathrm { HO } ^ { \ominus }$

A) I
B) II
C) III
D) IV
E) V

Question 6

$$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$$

-How does doubling the concentration of both the alkyl halide and the nucleophile in the above S_N2 reaction affect the rate of the reaction?

A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

Question 7

Which of the following alkyl halides undergoes an S_N2 reaction most rapidly?

A) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCH } _ { 2 } \mathrm { I }$
B) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCl }$
C) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHI }$
D) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$
E) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I }$

Question 8

Which of the following S_N2 reactions is the slowest?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br } ^ { - }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl } + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { Cl } ^ { - }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I } + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { I } ^ { - }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \mathrm {~F} + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { F } ^ { - }$
E)

Question 9

Which of the following S_N2 reactions is the fastest?

A)
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I } + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { I } ^ { - }$
C)
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br } ^ { - }$
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I } + \mathrm { H } _ { 2 } \mathrm { O } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { HI }$

Question 10

Which of the following is not a nucleophile?

A) $\mathrm { CH } _ { 3 } \mathrm { NH } _ { 2 }$
B) $\mathrm { H } _2 \mathrm { O }$
C) ${ } ^ { + } \mathrm { CH } _ { 3 }$
D) $\mathrm { CH } _ { 3 } \mathrm { O }^ { \ominus }$
E) $\mathrm { HC } \equiv \mathrm { C }^ { \ominus }:$

Question 11

The specific rotation of $( R ) - \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CHOHCH } _ { 3 } \text { is } - 42.3 \text {. A pure sample of } ( R ) - \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CHClCH } _ { 3 }$ was converted into the corresponding alcohol via a S_N2 eaction. What is the specific rotation of the product?

A) -42.3
B) between 0 and -42.3
C) between +42.3 and 0
D) +42.3

Question 12

Which of the following alkyl halides is the least reactive in an SN2 reaction?

A)CH₃CH₂Cl
B)
C)
D)
E)

Question 13

The specific rotation of (R)-sec-butyl alcohol is -13.52. A pure sample of (R)-sec-butyl bromide was converted to sec-butyl alcohol via an SN2 reaction. What is the specific rotation of
The product, assuming 100% yield?

A) -13.52
B) between 0 and -13.52
C) between 0 and +13.52
D) +13.52
E) zero

Question 14

Which of the following is not a nucleophile?

A) NH₃
B) NH₂CH₃
C) $\mathrm { HC } \equiv \mathrm { C } : ^-$
D) CH₃CH₂⁺

Question 15

What are the substitution products of the following reaction?
$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow \text { ? }$

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { BrH } ^ { + } + \mathrm { O } ^ { - }$
B) $\mathrm { HOCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { Br } ^ { - }$
D) $\mathrm { CH } _ { 2 } = \mathrm { CH } _ { 2 } + \mathrm { Br } ^ { - } + \mathrm { H } _ { 2 } \mathrm { O }$
E) $\mathrm { CH } _ { 2 } = \mathrm { CHBr } + \mathrm { H } _ { 2 } \mathrm { O }$

Question 16

$$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$$

-How does doubling the concentration of the alkyl halide in the above S_N2 reaction affect the rate of the reaction?

A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

Question 17

What product results from the S_N2 reaction between (R)-2-chloropentane and methoxide ion?

A) (R)-2-methoxypentane
B) (S)-2-methoxypentane
C) racemic 2-methoxypentane
D) 1-methoxypentane
E) 3-methoxypentane

Question 18

Which of the following alkyl halides reacts the fastest in an SN2 reaction?

A) 2-chloro-2-methylpropane
B) 2-chlorobutane
C) 1-chlorobutane
D) chloromethane

Question 19

Which of the following S_N2 reactions is the fastest?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \mathrm { OH } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { Br } ^ { - }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \mathrm { H } _ { 2 } \mathrm { O } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { HBr }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHBrCH } _ { 3 } + \mathrm { OH } ^ { - } \rightarrow \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CHOHCH } _ { 3 } + \mathrm { Br } ^ { - }$
D) $\mathrm { CH } _3 \mathrm { CH } _2 \mathrm { CHBrCH } _3 + \mathrm { H } _2 \mathrm { O } \rightarrow \mathrm { CH } _3 \mathrm { CH } _2 \mathrm { CHOHCH } _3 + \mathrm { HBr }$

Question 20

Which of the following is the best nucleophile in an SN2 reaction?

A) isopropoxide ion
B) tert-butoxide ion
C) ethoxide ion
D) tert-pentoxide ion

Question 21

Which alkyl halide undergoes an S_N2 reaction most rapidly?

A) 1-iodo-3-methylpentane
B) 2 -iodopentane
C) 2-iodo-2-methylpentane
D) 3 -iodopentane
E) 1 -iodo-2,2-dimethylpentane

Question 22

Which of the following is the best leaving group?

A) HO^-
B) F^-
C) Cl^-
D) Br^-
E) I^-

Question 23

Which of the following species is the least nucleophilic?

A) (CH₃)₃CO-
B) H₂O
C) (CH₃)₃N
D) HO^-
E) CN^-

Question 24

Which of the following alkyl halides reacts the fastest in an S_N1 reaction?

A)
B)
C)
D)
E)

Question 25

$\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}+\mathrm{I}^{\ominus} \longrightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{Br}^{\ominus}$


-How does doubling the concentration of the alkyl halide affect the rate of the above S_N1 reaction?

A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

Question 26

When (S)-1-bromo-1-phenylethane undergoes an S_N2 reaction with methanethiol (CH₃SH) the product of the reaction is the compound shown below. What is its configuration?

A) S only
B) R only
C) both R and S with slightly more S than R
D) both R and S with slightly more R than S

Question 27

S_N2 reactions usually proceed with ________.

A) equal amounts of inversion and retention at the asymmetric center undergoing substitution
B) slightly more inversion than retention at the asymmetric center undergoing substitution
C) slightly more retention than inversion at the asymmetric center undergoing substitution
D) complete inversion at the asymmetric center undergoing substitution
E) complete retention at the asymmetric center undergoing substitution

Question 28

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.

Question 29

The SN1 reaction of (CH₃)₃)CBr with water has ________ steps, ________ transition states, and ________ intermediates.

A) 2; 2; 2
B) 2; 2; 3
C) 2; 3; 2
D) 3; 2; 3
E) 3; 3; 2

Question 30

Which alkyl halide undergoes an S_N2 reaction most rapidly?

A)
B)
C)
D)
E)

Question 31

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

A) These alkoxides have the same nucleophilicity because the negative charge in both is on an oxygen atom.
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is decreased 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

Question 32

Which of the following factors has no effect on the rate of S_N1 eactions?

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

Question 33

Which of the following compounds is the most reactive in a S_N2 reaction?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { Cl }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { Br }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { I }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { F }$
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { OH }$

Question 34

Which of the following is the rate law for an S_N1 reaction?

A) $\text { rate } = k [ \text { alkyl halide] [nucleophile] }$
B) $\text { rate } = k [ \text { nucleophile } ]$
C) $\text { rate } = k [ \text { alkyl halide } ]$
D) $\text { rate } = k _ { 1 } \left[ \text { alkyl halide] [nucleophile] } + k _ { 2 } [ \text { alkyl halide] } \right.$
E) $\text { rate } = k 1 [ \text { alkyl halide } ] + k 2 [ \text { nucleophile] }$

Question 35

$\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}+\mathrm{I}^{\ominus} \longrightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{Br}^{\ominus}$


-How does doubling the concentration of both the alkyl halide and the nucleophile affect the rate of the abov S_N1 reaction?

A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

Question 36

$\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CBr}+\mathrm{I}^{\ominus} \longrightarrow\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{Br}^{\ominus}$


-How does doubling the concentration of the nucleophile affect the rate of the above S_N1 reaction?

A) no change
B) doubles the rate
C) triples the rate
D) quadruples the rate
E) rate is halved

Question 37

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$
B)
C)
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I }$
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$

Question 38

Which of the following alkyl halides reacts the fastest in a S_N1 reaction?

A) 2-chloro-2-methylpropane
B) 2-chlorobutane
C) 1-chlorobutane
D) chloromethane

Question 39

Which alkyl halide undergoes a SN2 reaction most rapidly?

A)
B)
C)
D)
E)

Question 40

Which alkyl halide is the most reactive in an S_N2 reaction?

A) $\left( \mathrm { CH } _ { 3 } \right) \mathrm { CCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm {~F}$
B) $\left( \mathrm { CH } _ { 3 } \right) \mathrm { CCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$
C) $\left( \mathrm { CH } _ { 3 } \right) \mathrm { CCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$
D) $\left( \mathrm { CH } _ { 3 } \right) \mathrm { CCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I }$
E) All primary halides react at the same rate in S_N2 reactions.

Question 41

What is the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 42

Which of the following alkyl halides reacts the fastest in an E2 reaction?

A) 2-chloro-2-methylbutane
B) 1-chlorobutane
C) 1-chloro-2-methylbutane
D) 2-chlorobutane
E) chloromethane

Question 43

What is the major product of the following E2 reaction?

A)
B)
C)
D)
E)

Question 44

Which of the following alkyl halides reacts the fastest in an E2 reaction?

A)
B)
C)
D)
E)CH₃I

Question 45

Which of the following alkyl chlorides forms only one alkene when it undergoes an elimination reaction?

A) 1-chloropentane
B) 2-chloropentane
C) 3-chloropentane
D) 1-chloro-2-methylbutane
E) 1-chloro-3-methylbutane

Question 46

What stereoisomer is the major product obtained from the following E2 reaction?

A)
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } = \mathrm { CH } _ { 2 }$
C)
D)
E)

Question 47

How many alkenes can be obtained as products (even in minor amounts) when the alkyl halide shown below undergoes an E2 reaction? (Count E/Z stereoisomers as different products.)

A) 1
B) 2
C) 3
D) 4
E) 5

Question 48

What is the major product of the following reaction?

A) 2,3-dimethyl-1-hexene
B) 2,3-dimethyl-2-hexene
C) 2 -isopropyl-1-pentene
D) (Z)-2,3 -dimethyl-3-hexene
E) (E)-2,3 -dimethyl-3-hexene

Question 49

Which of the following alkyl bromides undergo SN1 olvolysis reactions?

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

Question 50

Which of the following are the elimination products obtained from the following reaction?
$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow ?$

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } ^ { + } \mathrm { H } + \mathrm { O } ^ { - }$
B) $\mathrm { HOCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } + \mathrm { Br } ^ { - }$
D) $\mathrm { CH } _ { 2 } = \mathrm { CH } _ { 2 } + \mathrm { Br } ^ { - } + \mathrm { H } _ { 2 } \mathrm { O }$
E) $\mathrm { CH } _ { 2 } = \mathrm { CHBr } + \mathrm { H } _ { 2 } \mathrm { O }$

Question 51

Which of the following alkyl halides reacts the fastest in an E2 reaction?

A)
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { I }$
D)
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$

Question 52

Which of the following alkyl halides reacts the fastest in an E2 reaction?

A) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCH } _ { 2 } \mathrm { I }$
B) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCHICH } _ { 3 }$
C) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { Br }$
D) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { Cl }$
E) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$

Question 53

What kind of reaction is occurring below?

A) S_N1
B) S_N2
C) E1
D) E2
E) none of the above

Question 54

Using the following experimental data for the rate of the reaction given below:


$\begin{array} { | c | c | c | c | } \hline \text { Experiment \#1 } & \text { [Alkyl Halide] } & \text { [Base] } & \text { Rate } \\\hline 1 & 0.01 & 0.01 & 1 \\\hline 2 & 0.02 & 0.01 & 2 \\\hline 3 & 0.01 & 0.02 & 1 \\\hline\end{array}$
What kind of reaction is taking place?

A) S_N1
B) S_N2
C) E1
D) E2
E) none of the above

Question 55

What is the major product of the following reaction?

A)
B) $\mathrm { CH } _ { 2 } = \mathrm { CH } _ { 2 }$
C)
D) A and B
E) A and C

Question 56

Which of the following alkyl halides is the least reactive in an E2 reaction?

A) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCH } _ { 2 } \mathrm { I }$
B) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCHICH } _ { 3 }$
C) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { Br }$
D) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { Cl }$
E) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$

Question 57

Which of the following is least likely to be formed as a product when 2-iodopentane reacts with sodium ethoxide?

A) 1-ethoxypentane
B) 2-ethoxypentane
C) (Z)-2-pentene
D) (E)-2-pentene
E) 1-pentene

Question 58

Which of the following alkyl halides undergoes S_N1 solvolysis most rapidly?

A) cyclohexyl bromide
B) methyl iodide
C) isopropyl chloride
D) 3-chloropentane
E) 3-iodo-3-methylpentane

Question 59

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

A) The reactant is more soluble in polar solvents.
B) The reactant is less soluble in polar solvents.
C) The nucleophile is solvated by polar solvents.
D) Solvation by polar solvents stabilizes the carbocation more than it stabilizes the transition state.
E) Solvation by polar solvents stabilizes the transition statemore than it stabilizes the neutral reactant.

Question 60

Which of the following alkyl iodides undergoes S_N1 solvolysis most rapidly?

A) 1-iodo-3-methylpentane
B) 2-iodopentane
C) 2-iodo-2-methylpentane
D) 3 -iodopentane
E) 1 -iodo-2,2-dimethylpentane

Question 61

What is the substitution product of the following reaction?

Question 62

Draw the product of the following S_N2 eaction:

Question 63

Draw all possible alkene products of the following reaction and circle the major product:

Question 64

What two reactions occur when 2-iodohexane reacts with sodium ethoxide?

A) S_N2 and S_N1
B) $\text { E1 and E2 }$
C) S_N2 and E2
D) E1 and S_N1
E) E2 and E1

Question 65

What are the products of the following reaction?

A)
B) $\mathrm { CH } _ { 2 } = \mathrm { CH } _ { 2 }$
C)
D) A and B
E) A and C

Question 66

What are the products of the following reaction? Select all that apply.

A)
B)
C)
D)
E)
F)

Question 67

Which of the following statements is true about SN1 reactions of alkyl halides?

A) Complete inversion of configuration occurs.
B) The reactions are favored by nonpolar solvents.
C) The reactions are favored by polar solvents.
D) Reaction rates depend only on the concentration of the nucleophile.
E) The reaction occurs via a one-step back-side attack.

Question 68

Draw all possible alkene products of the following reaction and circle the major product:

Question 69

Do all primary alkyl iodides underg S_N2 eactions with sodium hydroxide in a given solvent at the same rate? Explain.

Question 70

Draw the substitution product of the following reaction:

Question 71

Draw the substitution product of the following reaction:

Question 72

Draw the substitution product of the following reaction:

Question 73

Draw the substitution product of the following reaction:

Question 74

Draw the substitution product of the following reaction:

Question 75

For each of the following reactions, indicate the alkyl halide that will form the greatest amount of the given product:

Question 76

What is the substitution product of the following reaction?

Question 77

Draw the substitution product of the following reaction:

Question 78

Draw the substitution product of the following reaction:

Question 79

When the nucleophile and the leaving group are contained in the same molecule, is an intermolecular or an intramolecular reaction more likely to occur? Explain.

Question 80

A student attempted to prepare 1-chlorobutane by reacting 1-butanol with a solution of NaCl. Did the student obtain the desired product? Explain.