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 stronger than the dipole-dipole and London dispersion forces present in alkyl halides.

Question 2

Which of the following compounds is classified as a vicinal dihalide?

Accepted Answer

$$\mathrm{CH_2ClCH_2Cl}$$

Question 3

What is the major product when 2-methyl-2-butanol reacts with concentrated HCl?

Accepted Answer

2-chloro-2-methylbutane

Question 4

Which of the following best describes the rate-determining step in the SN1 reaction of tert-butyl alcohol with HBr?

Accepted Answer

Formation of the carbocation intermediate

Question 5

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

Accepted Answer

$$\mathrm{I^-}$$

Question 6

Which solvent would most likely increase the rate of an SN2 reaction involving a primary alkyl halide and a strong nucleophile?

Accepted Answer

Acetone (a polar aprotic solvent)

Question 7

Which of the following statements about nucleophilicity is correct?

Accepted Answer

Nucleophilicity increases down a group in the periodic table in protic solvents.

Question 8

Which of the following alcohols will react fastest with HBr to form an alkyl bromide?

Accepted Answer

tert-Butyl alcohol

Question 9

What is the IUPAC name for the following compound?

(CH3)2CHCH2CH2Br

Accepted Answer

1-bromo-3-methylbutane

Question 10

Which of the following best explains why fluorinated hydrocarbons such as Teflon are used as non-stick coatings?

Accepted Answer

Fluorine's low polarizability leads to weak intermolecular forces, making the surface non-stick.

Question 11

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

Accepted Answer

The product is often racemic due to attack from either side of the planar carbocation.

Question 12

Which of the following is the correct order of increasing SN1 reactivity for the following alcohols: I (primary), II (secondary), III (tertiary)?

Accepted Answer

I \u003c II \u003c III

Question 13

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

Accepted Answer

$$\mathrm{H_2O}$$

Question 14

Which of the following best describes a geminal dihalide?

Accepted Answer

A compound with two halogen atoms bonded to the same carbon atom.

Question 15

Which of the following is a correct statement about the effect of polar protic solvents on SN1 and SN2 reactions?

Accepted Answer

Polar protic solvents increase the rate of SN1 reactions but decrease the rate of SN2 reactions.

Question 16

Which of the following is the correct IUPAC name for isobutyl alcohol?

Accepted Answer

2-methylpropan-1-ol

Question 17

Which of the following is a primary alcohol?

Accepted Answer

$$\mathrm{CH_3CH_2OH}$$

Question 18

Which of the following is the best explanation for why tertiary alkyl halides do not undergo SN2 reactions efficiently?

Accepted Answer

Steric hindrance prevents the nucleophile from attacking the electrophilic carbon.

Question 19

Which of the following is the correct order of leaving group ability for halide ions in SN2 reactions (best to worst)?

Accepted Answer

$$\mathrm{I^- \u003e Br^- \u003e Cl^- \u003e F^-}$$

Alkyl Halides and Alcohols: Nucleophilic Substitution and Related Concepts

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