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CHE 008B A01 SS1 2025 Lecture 13 - Nucleophilic Acyl Substitution

Multiple dropdown selections

Compared to a ketone adding a leaving group on a carboxylic acid derivative increases the number of resonance structures and  decreases the overall partial positive at the carbonyl carbon.  This is because the leaving group acts as an electron donor by resonance. If the leaving group  is O or N resonance is efficient due to good orbital overlap, and the leaving group ability is [ Select ] good bad cannot say due to pKa. This [ Select ] speeds up slows down does not affect. nucleophilic acyl substitution.

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The prompt describes how a leaving group that can participate in resonance with the carbonyl affects the acyl substitution process, and it presents two sets of dropdown choices to complete the statement. Option 1: Leaving-group ability is chosen as either good, bad, or cannot say due to pKa, in relation to how readily the leaving group can depart and stabilize its negative charge after departure. If the leaving group is capable of resonance donation (as with O or N in appropriate contexts), this can stabilize the transition state and influence the reactivity. Here, selecting ......Login to view full explanation

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