$$\text{Rate} = k[\text{CH}_3\text{Br}][\text{OH}^-]$$

$$\text{CH}_2=\text{CH}_2 + \text{HBr} \rightarrow \text{CH}_3\text{CH}_2\text{Br}$$

$$\text{F}^- \u003c \text{Cl}^- \u003c \text{Br}^- \u003c \text{I}^- \u003c \text{TosO}^-$$

Question 1

Which of the following statements best describes the functional group present in alkyl halides?

Accepted Answer

A halogen atom bonded to a saturated sp3-hybridized carbon atom

Question 2

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

Accepted Answer

Bromomethane

Question 3

What is the rate equation for an SN2 reaction between methyl bromide and hydroxide ion?

Accepted Answer

$$	ext{Rate} = k[	ext{CH}_3	ext{Br}][	ext{OH}^-]$$

Question 4

Which solvent would most likely increase the rate of an SN2 reaction?

Accepted Answer

Dimethyl sulfoxide (DMSO)

Question 5

Which of the following is the best leaving group for nucleophilic substitution reactions?

Accepted Answer

$$	ext{TosO}^-$$

Question 6

Which of the following statements about SN1 reactions is correct?

Accepted Answer

The reaction involves a carbocation intermediate

Question 7

Which of the following alkyl halides would react fastest in an SN1 reaction?

Accepted Answer

Tertiary bromide

Question 8

What is the order of carbocation stability from least to most stable?

Accepted Answer

Methyl \u003c Primary \u003c Allyl \u003c Benzyl \u003c Secondary \u003c Tertiary

Question 9

Which of the following nucleophiles is most reactive in an SN2 reaction?

Accepted Answer

$$	ext{HS}^-$$

Question 10

What is the expected stereochemical outcome of an SN2 reaction at a chiral carbon?

Accepted Answer

Inversion of configuration

Question 11

Which of the following best explains why tertiary alkyl halides are unreactive in SN2 reactions?

Accepted Answer

Steric hindrance prevents nucleophile attack

Question 12

Which of the following is a real-world application of alkyl halides?

Accepted Answer

They are used as inhaled anesthetics, refrigerants, and pesticides

Question 13

Which of the following reactions is an example of Markovnikov addition?

Accepted Answer

$$	ext{CH}_2=	ext{CH}_2 + 	ext{HBr} ightarrow 	ext{CH}_3	ext{CH}_2	ext{Br}$$

Question 14

Which of the following statements about the SN1 reaction rate is correct?

Accepted Answer

Doubling the alkyl halide concentration doubles the reaction rate

Question 15

Which of the following is a plausible reason why polar solvents enhance the rate of SN1 reactions?

Accepted Answer

They stabilize the carbocation intermediate

Question 16

Which of the following is the correct order of leaving group reactivity for nucleophilic substitution reactions?

Accepted Answer

$$	ext{F}^- \u003c 	ext{Cl}^- \u003c 	ext{Br}^- \u003c 	ext{I}^- \u003c 	ext{TosO}^-$$

Question 17

Which of the following best describes the mechanism of the SN1 reaction?

Accepted Answer

Formation of a carbocation intermediate followed by nucleophilic attack

Question 18

Which of the following would be the most reactive substrate in an SN2 reaction?

Accepted Answer

Methyl bromide

Question 19

Which of the following is a consequence of SN2 reactions at a chiral center?

Accepted Answer

The configuration is inverted

Question 20

Which of the following is NOT a characteristic of SN2 reactions?

Accepted Answer

Reaction involves a carbocation intermediate

Alkyl Halides: Structure, Properties, and Nucleophilic Substitution Mechanisms (SN1 & SN2)

Study Guide - Practice Questions