Look at the imide, the nitrogen analog of an anhydride below: a) For a neutral imide, will the carbonyl carbon be more (easier to attack) or less (harder to attack) electrophilic than the C of a neutral anhydride? b) If the imide is hydrolyzed under acidic conditions, which atom, one of the oxygens or the nitrogen, will be protonated? Explain your answer.
Look at the imide, the nitrogen analog of an anhydride below: a) For a neutral imide, will the carbonyl carbon be more (easier to attack) or less (harder to attack) electrophilic than the C of a neutral anhydride? b) If the imide is hydrolyzed under acidic conditions, which atom, one of the oxygens or the nitrogen, will be protonated? Explain your answer.
World of Chemistry, 3rd edition
3rd Edition
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Chapter2: Matter
Section: Chapter Questions
Problem 25A
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Question
Look at the imide, the nitrogen analog of an anhydride below:
a) For a neutral imide, will the carbonyl carbon be more (easier to attack) or
less (harder to attack) electrophilic than the C of a neutral anhydride?
b) If the imide is hydrolyzed under acidic conditions, which atom, one of the
oxygens or the nitrogen, will be protonated? Explain your answer.
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won't presence of a more electronegative atom, like nitrogen, near the carbonyl carbon in the imide results in decreased electron density around the carbon making it less electrophilic?
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