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2. Consider the following intramolecular aldol condensation. This result is fully consistent with the two rules we use to determine the likely product of intramolecular aldol condensation reactions. Rule 1: Only form 5 or 6 membered rings, rule 2: the less- hindered carbonyl group will serve as the electrophile. OH- H₂O product not formed Interestingly, if the same starting material is treated with a secondary amine such as pyrrolidine and some acid, the other product is formed preferentially. Describe the mechanism for what is happening in the presence of amine and acid. (6 points)

2. Consider the following intramolecular aldol condensation. This result is fully consistent with the two rules we use to determine the likely product of intramolecular aldol condensation reactions. Rule 1: Only form 5 or 6 membered rings, rule 2: the less- hindered carbonyl group will serve as the electrophile. OH- H₂O product not formed Interestingly, if the same starting material is treated with a secondary amine such as pyrrolidine and some acid, the other product is formed preferentially. Describe the mechanism for what is happening in the presence of amine and acid. (6 points)

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.3: Dehydration Of Aldol Products: Synthesis Of Enones
Problem 4P
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2. Consider the following intramolecular aldol condensation. This result is fully consistent with the two rules we use to determine the likely product of intramolecular aldol condensation reactions. Rule 1: Only form 5 or 6 membered rings, rule 2: the less- hindered carbonyl group will serve as the electrophile. OH- H₂O product not formed Interestingly, if the same starting material is treated with a secondary amine such as pyrrolidine and some acid, the other product is formed preferentially. Describe the mechanism for what is happening in the presence of amine and acid. (6 points)
Transcribed Image Text:2. Consider the following intramolecular aldol condensation. This result is fully consistent with the two rules we use to determine the likely product of intramolecular aldol condensation reactions. Rule 1: Only form 5 or 6 membered rings, rule 2: the less- hindered carbonyl group will serve as the electrophile. OH- H₂O product not formed Interestingly, if the same starting material is treated with a secondary amine such as pyrrolidine and some acid, the other product is formed preferentially. Describe the mechanism for what is happening in the presence of amine and acid. (6 points)
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