Question 1

Which of the following statements best explains why tertiary alcohols are more easily dehydrated than secondary or primary alcohols under acidic conditions?

Accepted Answer

Tertiary alcohols form more stable carbocations, lowering the activation energy for dehydration.

Question 2

A student attempts to convert 1-butanol to 1-bromobutane using HBr. Which mechanism is most likely to occur, and why?

Accepted Answer

An $$S_N2$$ mechanism, because primary alcohols do not form stable carbocations.

Question 3

Which reagent would best convert a secondary alcohol to a ketone without further oxidation to a carboxylic acid?

Accepted Answer

$$\mathrm{NaOCl, CH_3COOH, 0^\circ C}$$

Question 4

Which of the following best describes the product(s) when a secondary alkyl tosylate reacts with sodium ethoxide ($$\mathrm{NaOEt}$$)?

Accepted Answer

Both substitution and elimination products form.

Question 5

When 2-butanol is dehydrated with concentrated $$\mathrm{H_2SO_4}$$, which is the major product and why?

Accepted Answer

trans-2-butene, because it is the more stable (E) alkene.

Question 6

Which of the following statements about the reaction of epoxides with nucleophiles is correct?

Accepted Answer

Under acidic conditions, nucleophiles attack the more substituted carbon of the epoxide.

Question 7

A chemist wants to convert 1-propanol to 1-chloropropane. Which reagent(s) and conditions would be most effective?

Accepted Answer

$$\mathrm{HCl}$$ and $$\mathrm{$$ZnCl_2$$}$$

Question 8

Which of the following is NOT a possible product when a tertiary alcohol is treated with $$\mathrm{H_2SO_4}$$ and heat?

Accepted Answer

A primary alkyl halide

Question 9

Which of the following statements about the oxidation of alcohols is FALSE?

Accepted Answer

Tertiary alcohols can be oxidized to ketones.

Question 10

Which of the following best explains why amines do NOT undergo substitution and elimination reactions like alcohols?

Accepted Answer

Protonating an amine does not create a good leaving group.

Question 11

Which of the following is a correct statement about the stereochemistry of products when an alcohol is converted to a sulfonate ester and then reacts with a nucleophile via $$S_N2$$?

Accepted Answer

The product has the opposite configuration to the original alcohol.

Question 12

Which of the following statements about Grignard reagents is TRUE?

Accepted Answer

They are strong nucleophiles and react with electrophiles.

Question 13

A chemist treats 2-butanol with $$\mathrm{$$PBr_3$$} in $$pyridine. What is the expected product and mechanism?

Accepted Answer

2-bromobutane via $$S_N2$$ mechanism

Question 14

Which of the following is the best explanation for why tosylate is an excellent leaving group?

Accepted Answer

It is a weak base stabilized by electron delocalization.

Question 15

Which of the following is a correct statement about the reaction of ethers with strong acids?

Accepted Answer

Ethers react with strong acids via $$S_N2 or$$ $$S_N1$$ mechanisms depending on the stability of the carbocation.

Question 16

Which of the following is a correct statement about the Hofmann elimination?

Accepted Answer

The major product is the least substituted alkene.

Question 17

Which of the following best describes the role of pyridine in the reaction of alcohols with $$\mathrm{$$SOCl_2$$}$$?

Accepted Answer

It acts as a base to neutralize HCl formed in the reaction.

Question 18

Which of the following statements about organocuprate (Gilman) reagents is TRUE?

Accepted Answer

They can replace halides (Cl, Br, I) with alkyl groups in organic molecules.

Question 19

Which of the following is the correct order of leaving group ability (from best to worst) for the following: sulfonate ester, alcohol, alkyl halide, amine?

Accepted Answer

sulfonate ester \u003e alkyl halide \u003e alcohol \u003e amine

Question 20

Which of the following is a correct statement about the use of thionyl chloride ($$\mathrm{$$SOCl_2$$}) in $$alcohol chemistry?

Accepted Answer

It converts alcohols to alkyl chlorides via a chlorosulfite intermediate.

Reactions of Alcohols, Ethers, Epoxides, Amines, Sulfur-Containing Compounds, and Introduction to Organometallic Compounds

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