Give the major product of the following reaction (after aqueous workup). If no reaction occurs,...

Question:

Give the major product of the following reaction (after aqueous workup). If no reaction occurs, draw the starting material.

Cyclic acetals:

Ketones can be converted to cyclic acetals. Cyclic acetals are normally used as protecting groups for ketones. Cyclic acetals can be prepared by the acid catalyzed reaction between a ketone and 1,2-ethanediol.

Answer and Explanation:

The product of the reaction is given below:

This is formation of a cyclic acetal. The mechanism is given below.

Step 1: Protonation

Step 2: Nucleophilic attack by the diol on the carbonyl carbon

Step 3: Loss of water as the leaving group

Step 4: Intramolecular nucleophilic attack form the cyclic acetal


Learn more about this topic:

Formation of Cyclic Acetals
Formation of Cyclic Acetals

from Organic Chemistry: Help & Review

Chapter 3 / Lesson 15
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