$$\text{Rate} = k[\text{alkyl halide}][\text{nucleophile}]$$

Question 1

Which of the following best describes a vinyl halide?

Accepted Answer

A halogen bonded to an sp\^2 carbon of an alkene.

Question 2

Which of the following statements about the carbon-halogen bond in alkyl halides is correct?

Accepted Answer

The carbon atom has a partial positive charge, making it susceptible to nucleophilic attack.

Question 3

What is the correct IUPAC name for the following compound: CH\_3CH\_2CH(Br)CH\_2CH\_3?

Accepted Answer

3-bromopentane

Question 4

Which of the following is a geminal dihalide?

Accepted Answer

CH\_2Br\_2

Question 5

Which property most strongly influences the boiling point of alkyl halides?

Accepted Answer

Molar mass

Question 6

Arrange the following alkyl halides in order of increasing boiling point: CH\_3CH\_2Br, CH\_3CH\_2CH\_2Br, (CH\_3)\_3CBr, CH\_3CH\_2F.

Accepted Answer

CH\_3CH\_2F \u003c (CH\_3)\_3CBr \u003c CH\_3CH\_2Br \u003c CH\_3CH\_2CH\_2Br

Question 7

Which of the following alkyl halides is less dense than water?

Accepted Answer

CH\_3CH\_2Cl

Question 8

Why is bromination more selective than chlorination in free radical halogenation?

Accepted Answer

Bromine radicals are less reactive and favor formation at more substituted carbons.

Question 9

Which reagent is commonly used for allylic bromination and keeps Br\_2 concentration low?

Accepted Answer

N-Bromosuccinimide (NBS)

Question 10

What is the rate law for an S\_N2 reaction?

Accepted Answer

$$	ext{Rate} = k[	ext{alkyl halide}][	ext{nucleophile}]$$

Question 11

Which of the following best explains why tertiary alkyl halides do not undergo S\_N2 reactions?

Accepted Answer

Steric hindrance prevents nucleophilic attack from the backside.

Question 12

What is the stereochemical outcome of an S\_N2 reaction at a chiral center?

Accepted Answer

Inversion of configuration (Walden inversion)

Question 13

Which of the following is the strongest nucleophile in a polar protic solvent?

Accepted Answer

$$	ext{I}^-$$

Question 14

Which solvent would most effectively increase the rate of an S\_N2 reaction?

Accepted Answer

Dimethyl sulfoxide (DMSO)

Question 15

What is the key intermediate in an S\_N1 reaction?

Accepted Answer

Carbocation

Question 16

Which of the following alkyl halides would undergo S\_N1 solvolysis most rapidly?

Accepted Answer

3-iodo-3-methylpentane

Question 17

Which of the following is NOT a nucleophile?

Accepted Answer

Cyclohexane

Question 18

Which factor increases the nucleophilicity of an anion in the presence of a crown ether?

Accepted Answer

The cation is solvated, freeing the anion to react.

Question 19

Which of the following best describes the effect of polar protic solvents on nucleophilicity?

Accepted Answer

They decrease nucleophilicity by hydrogen bonding to the nucleophile.

Question 20

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

Accepted Answer

$$	ext{I}^-$$

Alkyl Halides and Nucleophilic Substitution (Chapter 6 Study Notes)

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