Question

What enone product would you expect to obtain from intramolecular aldol condensation of hexanedial? You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. Rings containing fewer than 5 atoms are too strained to be formed in this reaction. If more than one structure fits the description, draw them all. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu.

Answer 1

1-(cyclopent-1-en-1-yl)ethanone is the product.

Step-by-step explanation:

Intramolecular aldol condesation of hexanedial will produce a 5-membered cyclic enone.

At first, deprotonation takes place from carbon atom adjacent to any one of the two aldehyde groups.

Then the resulting carbanion gives intramolecular nucleophilic addition reaction at the carbonyl center of another aldehyde group.

Then protonation of resulting alkoxide ion takes place.

Lastly, dehydration takes place to produce cyclic enone.

Reaction mechanism and structure of product has been shown below.