Deck 7: Haloalkanes

Question 1

Arrange the nucleophiles in order of increasing reactivity (least reactive first).

A) III, II, I, IV
B) IV, I, II, III
C) I, III, II, IV
D) III, I, IV, II

Answer 1

III, I, IV, II

Question 2

Which is the best reaction condition for preparing 2-iodohexane from 1-hexene?

A) I₂ / CCl₄
B) HI
C) NaI
D) HIO₄

Answer 2

HI

Question 3

Which of the following structures have correct common names?

A) I, II
B) III, IV
C) I, III
D) II, IV

Answer 3

I, II

Question 4

Which of the following haloalkanes is prepared from the following reaction?

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

Question 5

Which of the reactions below are most likely to be S_N2 reactions?

A) I, II
B) II, III
C) III, IV
D) I, IV

Question 6

Which of the following structures have the correct IUPAC names?

A) I, II
B) III, IV
C) I, III
D) II, IV

Question 7

Which of the following halides is prepared from the following reaction?

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

Question 8

Arrange the leaving groups in order of increasing leaving group ability (least reactive first).

A) I, III, II, IV
B) III, I, IV, II
C) IV, II, I, III
D) IV, III, II, I

Question 9

Arrange the leaving groups in order of increasing leaving group ability (least first).

A) IV, I, III, II
B) III, I, IV, II
C) II, IV, I, III
D) II, III, I, IV

Question 10

Which statements apply to an S_N2 reaction?
I. The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II. The order of reactivity is methyl > 1°>2°>3°.
III. The rate limiting step of the reaction involves only the alkyl halide.
IV. There is an intermediate carbocation.

A) I, II
B) III, IV
C) I, IV
D) II, IV

Question 11

Which compounds are primary haloalkanes?

A) I, II
B) III, IV
C) II, III
D) I, IV

Question 12

Which of the reactions below are most likely to be S_N1 reactions?

A) I, II
B) II, III
C) III, IV
D) I, IV

Question 13

Which compounds are tertiary haloalkanes?

A) I and II
B) II and III
C) III and IV
D) II and IV

Question 14

Which statements apply to an S_N1 reaction?
I. The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II. The order of reactivity is methyl < 1°< 2° < 3°.
III. The rate limiting step of the reaction involves only the alkyl halide.
IV. There is an intermediate carbocation.

A) I, II
B) III, IV
C) I, IV
D) II, III

Question 15

Arrange the nucleophiles in order of increasing reactivity (least reactive first).

A) I, IV, II, III
B) IV, II, I, III
C) II, I, IV, III
D) IV, III, I, II

Question 16

Arrange the haloalkanes in order of increasing reactivity in an S_N2 reaction with KI in acetone (least first).

A) I, IV, III, II
B) IV, I, III, II
C) II, III, I, IV
D) III, II, IV, I

Question 17

Which compounds are secondary haloalkanes?

A) I and III
B) II and III
C) I and II
D) II and IV

Question 18

Which of the following compounds are secondary haloalkanes?
I. Isobutyl bromide
II. 2-iodobutane
III. isopropyl fluoride
IV. neopentyl chloride

A) I, II
B) III, IV
C) II, III
D) I, IV

Question 19

Which of the following halides is prepared from the following reaction?

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

Question 20

Arrange the haloalkanes in order of increasing rate of solvolysis (slowest first) in ethanol.

A) IV, III, II, I
B) I, II, III, IV
C) III, II, I, IV
D) II, III, I, IV

Question 21

Which reaction below should give the best yield of isopropyl methyl ether?

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

Question 22

Which nucleophilic substitution reaction will proceed?

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

Question 23

The starting material needed to complete the following reaction is,

Question 24

Which of the following alkyl halides yields the product shown as the only possible product of an E2 reaction?"

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

Question 25

Which reaction proceeds according to an E1 mechanism?

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

Question 26

Which solvents are polar protic?
I. ethanol
II. hexane
III. DMSO
IV. water

A) III, IV
B) II, III
C) I, IV
D) I, III

Question 27

Which solvents are nonpolar (apolar)?
I. DMSO
II. pentane
III. methanol
IV. diethyl ether

A) II, III
B) III, IV
C) I, III
D) II, IV

Question 28

What products are formed in the E2 reaction shown below?

A) I and II
B) II and III
C) III and IV
D) II and IV

Question 29

The major product of the following reaction is,

Question 30

Which reactions will proceed with inversion of configuration?

A) I, II
B) III, IV
C) II, III
D) I, IV

Question 31

What is the major product from an elimination reaction starting with 2-bromopentane?

A) 1-pentene
B) cis-2-pentene
C) trans-2-pentene
D) a mixture of cis and trans-2-pentene

Question 32

What product is formed in the E1 reaction shown below?

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

Question 33

Which solvents are polar aprotic?
I. DMSO
II. H₂O
III. Acetone
IV. Formic acid

A) II, III
B) III, IV
C) I, III
D) II, IV

Question 34

1-bromo-4-(bromomethyl)cyclohexane reacts with potassium methoxide in methanol. What is the chemical structure of the product that is formed at room temperature?

Question 35

Which reaction below proceeds via an E2 mechanism?

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

Question 36

The starting material needed to complete the following reaction is,

Question 37

The major products of the following reaction are,

Question 38

Which statement or statements is/are true for an E1 reaction?
I. The rate limiting step of the reaction involves only the alkyl halide.
II. The rate limiting step of the reaction involves the alkyl halide and the base.
III. There is an intermediate carbocation.
IV. The order of reactivity is 1°>2°>3°.

A) I, III
B) II
C) I, III, IV
D) II, IV

Question 39

Which reactions proceed according to an E2 mechanism?

A) I and II
B) II and III
C) III and IV
D) I and IV

Question 40

Which of the reactions below is most likely to proceed via an S_N1 mechanism?

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

Question 41

The following nucleophiles are listed in decreasing order of S_N2 reactivity.

Question 42

The name of the following compound is (4R, 2E) - 4-bromo-2-pentene.

Question 43

The major products of the following reaction are,

Question 44

1-bromo-4-(bromomethyl)cyclohexane reacts with potassium methylthiolate in dimethylsulfoxide. Draw the chemical structure of the product that is formed at room temperature?

Question 45

The alkyl halides below are listed in decreasing order of S_N1 reactivity.

Question 46

The major product of the reaction of bromocyclohexane and potassium tert-butoxide in water is an ether.

Question 47

The reagent needed to complete the following reaction is,

Question 48

The major product of the reaction of R-2-bromobutane with potassium cyanide in acetone is S-2-methylbutanenitrile

Question 49

The major product of the reaction of R-2-bromobutane with water is a racemic alcohol.

Question 50

1-chloro-4-(chloromethyl)cyclohexane reacts if heated until HCl leaves the molecule. What is the chemical structure of the product?

Question 51

1-Chloro-4-(chloromethyl)cyclohexane reacts with two molecules of potassium-tert-butoxide in dimethylformamide. What are the two intermediate reaction products and the final reaction product formed?

Question 52

The alkyl halides below are listed in decreasing order of S_N2 reactivity.

Question 53

The name of the following compound is cis- (1R,2S)-1-chloro-2-bromocyclohexane.

Question 54

The reagent needed to complete the following reaction is,

Question 55

The reagent needed to complete the following reaction is,

Question 56

Polar aprotic solvents favor S_N1 reactions.

Question 57

Major substitution and elimination products of the following reaction are:

Question 58

The following nucleophiles are listed in decreasing order of S_N2 reactivity.