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2.there are four aldol condensation products possible when acetone and propanal are mixed in the presence of base. Use mechanistic sequences to illustrate what are they and how are they formed? (assume condensation only occurs without dehydration!)
Accepted Answer
The four aldol condensation products formed from the reaction of acetone and propanal in the presence of base (without dehydration) are:
1. (E)-4-Hydroxy-4-methylhex-2-enal: Acetone acts as the enolate, attacking the carbonyl carbon of propanal.
2. (Z)-4-Hydroxy-4-methylhex-2-enal: Same as above, but with the hydroxyl group and methyl group on the same side of the double bond.
3. 3-Hydroxy-2-methylpentanal: Propanal acts as the enolate, attacking the carbonyl carbon of acetone.
4. (E)-3-Hydroxy-2-methylpent-2-enal: Same as above, but with the hydroxyl group and methyl group on the same side of the double bond.
These four products arise due to the possible combinations of enolate formation and electrophilic attack. The stereochemistry (E/Z) is determined by the relative position of the substituents on the double bond. Note: Since the reaction occurs without dehydration, no alkenes are formed.
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