Question 1

Which of the following statements best describes the role of a Grignard reagent in organic synthesis?

Accepted Answer

It acts as a strong nucleophile, attacking electrophilic carbonyl carbons.

Question 2

What is the product when a Grignard reagent reacts with an ester followed by aqueous workup?

Accepted Answer

A tertiary alcohol

Question 3

Which reagent can be used to convert a primary alcohol to an alkyl chloride?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 4

Which of the following alcohols will be most easily dehydrated to form an alkene under acidic conditions?

Accepted Answer

Tertiary alcohol

Question 5

What is the major product when 2-butanol is oxidized with a strong oxidizing agent?

Accepted Answer

2-Butanone

Question 6

Which of the following is a 'green' alternative to chromium-based oxidation of alcohols?

Accepted Answer

Swern oxidation

Question 7

What is the product of the following reaction: $$\mathrm{PhMgBr} ($$Grignard reagent) + $$\mathrm{CH_3CHO} ($$acetaldehyde) followed by $$\mathrm{H_2O}$$?

Accepted Answer

1-Phenylethanol

Question 8

Which of the following statements about phenols is TRUE?

Accepted Answer

Phenols are more easily oxidized than tertiary alcohols.

Question 9

Which of the following best explains why tertiary alcohols do not undergo oxidation under normal conditions?

Accepted Answer

They lack an alpha hydrogen.

Question 10

What is the product when 1,2-ethanediol is treated with $$\mathrm{$$HIO_4$$}$$?

Accepted Answer

Two molecules of formaldehyde

Question 11

Which of the following reagents will reduce a carboxylic acid to a primary alcohol?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$

Question 12

Which of the following is the correct order of acidity (most to least acidic) for the following compounds: phenol, ethanol, water?

Accepted Answer

Phenol \u003e Water \u003e Ethanol

Question 13

Which of the following best describes the product of the reaction of 2-propanol with $$\mathrm{$$PBr_3$$}$$?

Accepted Answer

2-Bromopropane

Question 14

Which of the following is a correct statement about the dehydration of alcohols?

Accepted Answer

The reaction follows Zaitsev's rule and yields the more substituted alkene.

Question 15

Which of the following is the correct IUPAC name for the compound shown below?

$$\mathrm{HO{-}C_6H_4{-}CH_3$} ($$hydroxyl group at position 1, methyl at position 4)

Accepted Answer

4-methylphenol

Question 16

Which of the following best explains why $$\mathrm{$$LiAlH_4$$} is a $$stronger reducing agent than $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

The Al-H bond is more polarized, making hydride more nucleophilic.

Question 17

Which of the following is the product of the acid-catalyzed hydration of 1-methylcyclohexene?

Accepted Answer

2-methylcyclohexanol

Question 18

Which of the following is a correct statement about the Swern oxidation?

Accepted Answer

It uses DMSO and oxalyl chloride to oxidize alcohols without using toxic chromium reagents.

Question 19

Which of the following best describes the product of the reaction of ethylene glycol with periodic acid ($$\mathrm{$$HIO_4$$}$$)?

Accepted Answer

Two molecules of formaldehyde

Question 20

Which of the following is the correct mechanism for the reaction of a Grignard reagent with a ketone?

Accepted Answer

Nucleophilic addition to the carbonyl carbon followed by protonation

Alcohols, Phenols, and Their Reactions: Organic Chemistry Study Guide

Study Guide - Practice Questions

Study Guide - Flashcards