Give the major product of the following reaction (after aqueous workup). If no reaction occurs, draw the starting material.
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
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from Organic Chemistry: Help & ReviewChapter 3 / Lesson 15