21. Aldehydes and Ketones: Nucleophilic Addition

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(d)

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(e)

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive.

There are three dioxane isomers: 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solvent for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Propose a mechanism for the acid hydrolysis of the third isomer.

Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.

Which of the following are a. hemiacetals? b. acetals? c. hydrates?

1.

Which of the following are a. hemiacetals? b. acetals? c. hydrates?

3.

Identify A through O:

In Section 17.7.4, we studied the acid-catalyzed hydrolysis of acetals. The acetal shown here resists hydrolysis by the mechanism in Figure 17.63. Why? [Draw the intermediates as if the reaction would occur, then analyze the intermediates for any problems.]