Orgo Unit 9.2 Discussion

Orgo Unit 9.2 Discussion - Topic #2: Arrange the following...

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Topic #2: Arrange the following in order of decreasing reactivity to nucleophilic acyl substitution: ester, amide, acid anhydride. Explain your logic. You should include: 1) The order in decreasing reactivity 2) Discussion of these factors as they pertain to the above compounds: carbonyl carbon delta +, resonance, steric effects, and leaving group. Ranking: 1. Acid Anhydride (most reactive) 2. Ester 3. Amide (least reactive) 1. Acid Anhydrides: According to Klein’s Organic Chemistry, anhydrides are almost as reactive as acyl halides, which are the most reactive of the carboxylic acid derivatives we have discussed so far. Like the other carboxylic acid derivatives, anhydrides have electrophilic carbon atoms on the carbonyls with a delta + partial positive charge, given their bonds with the more electronegative oxygen atoms. How electrophilic the carbon of the carbonyl group is will also depend on the substituents bonded to the molecule. R groups that are strongly electron-donating will decrease the delta + charge on the carbon of the carbonyl. Meanwhile, the oxygen atom that is bonded to the carbonyl carbons will also withdraw electrons density, and enhance the electrophilicity of these molecules. Their ability to withdraw electrons from the carbonyl carbons are not as great as those for acyl
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This note was uploaded on 04/10/2011 for the course AAS 410.302.81 taught by Professor Thompson during the Spring '11 term at Johns Hopkins.

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Orgo Unit 9.2 Discussion - Topic #2: Arrange the following...

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