Question 1

Which of the following statements best explains why alcohols generally have higher boiling points than alkyl halides of similar molecular weight?

Accepted Answer

Alcohols can form hydrogen bonds, which are much stronger than the dipole-dipole interactions in alkyl halides.

Question 2

Which of the following compounds is a geminal dihalide?

Accepted Answer

$$\mathrm{CH_3CHCl_2}$$

Question 3

What is the IUPAC name for the following compound?

(See image 17)

Accepted Answer

4-bromo-5-ethyl-2-methylheptane

Question 4

Which of the following best describes the effect of polarizability on the boiling points of alkyl halides?

Accepted Answer

Boiling point increases as polarizability increases due to stronger London dispersion forces.

Question 5

Which of the following alcohols is most soluble in water?

Accepted Answer

tert-butyl alcohol

Question 6

Which of the following is the correct order of SN1 reactivity for the C$$_5H$_{12}O $$alcohols I-III?

Accepted Answer

I, III, II

Question 7

Which of the following is the best leaving group for an SN2 reaction?

Accepted Answer

$$\mathrm{I^-}$$

Question 8

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

Accepted Answer

The reaction proceeds through a planar carbocation intermediate.

Question 9

What is the major product of the reaction between 1-methylcyclohexanol and HBr?

Accepted Answer

1-bromo-1-methylcyclohexane

Question 10

Which of the following best explains why SN2 reactions are faster in polar aprotic solvents?

Accepted Answer

Polar aprotic solvents do not solvate anions strongly, increasing nucleophilicity.

Question 11

Which of the following is the rate-determining step in the SN1 reaction of cyclopentanol with HBr?

Accepted Answer

Carbocation formation

Question 12

Which of the following is the least able to serve as a nucleophile in a chemical reaction?

Accepted Answer

$$\mathrm{CH_3$^+}$$

Question 13

Which of the following best describes a vicinal dihalide?

Accepted Answer

Two halogen atoms bonded to adjacent carbon atoms.

Question 14

Which of the following is a correct statement about the stereochemistry of the SN1 reaction?

Accepted Answer

The SN1 reaction often gives a racemic mixture due to attack from either side of the planar carbocation.

Question 15

Which of the following is the correct IUPAC name for the compound shown in image 18?

Accepted Answer

3,4-dimethyl-2-pentanol

Question 16

Which of the following is the best explanation for why tertiary alcohols react faster with hydrogen halides than primary alcohols?

Accepted Answer

Tertiary carbocations are more stable, making carbocation formation easier.

Question 17

Which of the following is a real-life application of fluorinated hydrocarbons such as $$-\mathrm{CF_2$-CF_2$}-$$?

Accepted Answer

Used as a non-stick coating for frying pans (Teflon).

Question 18

Which of the following is the correct IUPAC name for the compound shown in image 19?

Accepted Answer

trans-2-methylcyclopentanol

Question 19

Which of the following is the correct classification for 2-methyl-3-pentanol?

Accepted Answer

Secondary (2$$^\circ) $$alcohol

Alkyl Halides and Alcohols: Nucleophilic Substitution, Structure, Properties, and Mechanisms

Study Guide - Practice Questions