Textbook Question
Write the structures of the hemiacetal or hemiketal that result from reactions (a) and (b). Write the structures of the complete hydrolysis products of the acetal or ketal in (c) and (d).
a. Acetone + Ethanol → ?
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15. Aldehydes and Ketones
Hemiacetal and Acetal Formation
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Draw the intermediate in the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the starting material and the product in the reaction. The starting material is an aldehyde, and the product is an acetal.
Recognize that the reaction involves the formation of an acetal from an aldehyde in the presence of an alcohol and an acid catalyst.
Understand that the mechanism involves the formation of a hemiacetal intermediate. This occurs when the aldehyde reacts with one equivalent of alcohol.
The first step in the mechanism is the protonation of the carbonyl oxygen of the aldehyde, making the carbonyl carbon more electrophilic.
The alcohol then attacks the electrophilic carbonyl carbon, leading to the formation of a hemiacetal intermediate, which is characterized by an -OH and an -OR group on the same carbon.
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