Question 1

Which of the following statements best explains why tertiary alkyl radicals are more stable than primary alkyl radicals?

Accepted Answer

Tertiary alkyl radicals are stabilized by hyperconjugation and inductive effects from three adjacent alkyl groups.

Question 2

In mass spectrometry, the molecular ion peak (M$$^+) $$provides which of the following pieces of information?

Accepted Answer

The molecular weight of the compound.

Question 3

Which of the following is the correct order of reactivity for the radical halogenation of alkanes?

Accepted Answer

$$3^\circ \u003e 2^\circ \u003e 1^\circ$$

Question 4

Which IR absorption is most characteristic for the O-H stretch in alcohols?

Accepted Answer

$$3200-3600\ \mathrm{cm}^{-1} ($$broad)

Question 5

Which of the following reactions best describes the dehydration of a secondary alcohol?

Accepted Answer

An $$E1$$ elimination reaction producing an alkene.

Question 6

A chemist wants to synthesize an epoxide from an alkene. Which reagent would be most appropriate?

Accepted Answer

A peracid such as $$m-$$chloroperoxybenzoic acid ($$m-$$CPBA)

Question 7

Which of the following best describes the mechanism for the nucleophilic substitution of an epoxide under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon via an $$S_N2$$ mechanism.

Question 8

Which of the following carboxylic acid derivatives is most reactive toward nucleophilic acyl substitution?

Accepted Answer

Acyl chloride

Question 9

Which of the following statements about saponification is correct?

Accepted Answer

It is the base-catalyzed hydrolysis of an ester to produce a carboxylate salt and an alcohol.

Question 10

Which of the following best explains why soaps form micelles in water?

Accepted Answer

Soap molecules have hydrophobic tails and hydrophilic heads, allowing them to aggregate with tails inward and heads outward.

Question 11

Which reagent would convert a carboxylic acid to an acyl chloride?

Accepted Answer

$$\mathrm{$$SOCl_2$$} ($$thionyl chloride)

Question 12

A student treats an aldehyde with $$\mathrm{$$NaBH_4$$} in $$methanol. What is the major product?

Accepted Answer

A primary alcohol

Question 13

Which of the following reactions would best synthesize a tertiary alcohol?

Accepted Answer

Addition of a Grignard reagent to a ketone

Question 14

Which of the following is a correct statement about the reaction of an aldehyde with a primary amine?

Accepted Answer

It forms an imine (Schiff base) via nucleophilic addition followed by elimination of water.

Question 15

Which of the following best describes the product when a nitrile is hydrolyzed under acidic conditions?

Accepted Answer

A carboxylic acid

Question 16

A chemist wants to distinguish between an aldehyde and a ketone using IR spectroscopy. Which absorption is most useful?

Accepted Answer

A strong $$C-H$$ stretch just above $$2700\ \mathrm{cm}^{-1}$$ for aldehydes

Question 17

Which of the following statements about the hydrolysis of esters is correct?

Accepted Answer

Acid-catalyzed hydrolysis of an ester yields a carboxylic acid and an alcohol.

Question 18

Which of the following best describes the product of the reaction between an acyl chloride and ammonia?

Accepted Answer

An amide

Question 19

Which of the following is a correct statement about the reaction of a ketone with a Grignard reagent ($$\mathrm{RMgX}$$)?

Accepted Answer

It forms a tertiary alcohol after acidic workup.

Question 20

Which of the following best explains why amides are less reactive than esters toward nucleophilic acyl substitution?

Accepted Answer

The lone pair on nitrogen delocalizes into the carbonyl, stabilizing the amide.

Organic Chemistry Study Guide: Radicals, Spectroscopy, Alcohols, Amines, Ethers, Epoxides, Carboxylic Acids, Aldehydes, and Ketones

Study Guide - Practice Questions