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Chapter 16: Q39P (page 770)

Which of the following are

a. hemiacetals?

b. acetals?

c. hydrates?

Short Answer

Expert verified

a. Hemiacetals- Compounds 1, 7, 8

b. Acetals- Compounds 2, 3, 5

c. Hydrates- Compounds 4, 6

Step by step solution

01

Step-by-Step Solution Step 1: Acetals and hemiacetals

Hemiacetals and acetals are formed by reacting a carbonyl compound with alcohol.

Aldehydes and ketones react with alcohol in the presence of an acid. The acid catalyst activates the carbonyl.

The oxygen of the carbonyl group forms a bond with proton making the carbonyl carbon more electrophilic. The oxygen atom of the alcohol reacts with the electrophilic centre forming hemiacetal. Hemiacetals contain an 鈥揙H group (hydroxyl group) and an 鈥揙R group (alkoxy group) attached to the same carbon atom.

Hemiacetals react with another alcohol molecule to form acetals in the same mechanism. Acetals contain two 鈥揙R groups attached to the same carbon.

02

Hydrates

Compounds formed by the reaction of carbonyl compounds with water are called hydrates, and the reaction is called hydrolysis.

Acids or bases catalyze it. The catalyst is used to activate the carbonyl compound.

Hydrates contain two 鈥揙H groups attached to the same carbon atoms. Therefore, hydrates are germinal diols.

03

Identifying acetals, hemiacetals and hydrates

Compound 1-

It contains a hydroxyl group and a methoxy group attached to the same carbon atom. Therefore, it is a hemiacetal.

Compound 2-

It contains two ethoxy groups attached to the same carbon atom. Therefore, it is an acetal.

Compound 3-

The compound contains two methoxy groups attached to the same carbon atom. Therefore, it is an acetal.

Compound 4-

It contains two hydroxyl groups attached to the same carbon atom. Therefore, it is a hydrate.

Compound 5-

The compound contains two methoxy groups attached to the same carbon atom. Therefore, it is an acetal.

Compound 6-

It contains two hydroxyl groups attached to the same carbon atom. Therefore, it is a hydrate.

Compound 7-

It contains a hydroxyl group and a methoxy group attached to the same carbon atom. Therefore, it is a hemiacetal.

Compound 8-

It contains a hydroxyl group and a methoxy group attached to the same carbon atom. Therefore, it is a hemiacetal.

Therefore, the acetals, hemiacetals and hydrates of the given compound can be given as follows:

a. Hemiacetals- Compounds 1, 7, 8

b. Acetals- Compounds 2, 3, 5

c. Hydrates- Compounds 4, 6

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Most popular questions from this chapter

a. Would you expect hemiacetals to be stable in basic solutions? Explain your answer.

b. Acetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-

c. Can the rate of hydrate formation be increased by hydroxide ion as well as by acid? Explain.

Question: Propose a mechanism for each of the following reactions:

Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form acompound with molecular formula C11H14. What product is obtained from the Wittig reaction?

List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols

Question: What are the products of the following reactions? (A trace amount of acid is present in each case.)

a. cyclopentanone + ethylamine

b. cyclopentanone + diethylamine

c. acetophenone + hexylamine

d. acetophenone + cyclohexylamine
See all solutions

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