IV. Predicting reactions Reactions at the carbonyl group of acid derivatives are

Question

IV. Predicting reactions Reactions at the carbonyl group of acid derivatives are referred to as nucleophilic acyl substitution reactions ul Tetrahedral carbonyl addition intermediate Substitution product a) How does this reaction differ from the nucleophilc addition reactions at the carbonyl of aldehydes and ketones? HINT: Consider the fate of the tetrahedral intermediate b) Refer to fiqure 18.1 on page 714 of your textbook (7th edition) when For each reaction, identify the nucleophile and potential leaving group Which of the following reactions would occur quickly under mild conditions? If the reaction will not occur, briefly explain why a) CH2CNH2NaCI CH3CCINaNH2 C-C CH3NH2 ?_NHCH3 +HCl c) (CH3)2CHCNH2 CH3OH(CH3)2CHCOCH3 NH3 HaC CHa CH3NH2 + CH3COOH H3C NHCH3

Explanation / Answer

4. A. Nucleophilic Substitution at acyl group involved in the formation of tetrahedral intermediate. And one group at acyl carbon is substituted by another group

B. A. Cl is nucleophile and NH2 is the leaving group.

B. Cl is the leaving group and NH2 is the nucleophile

C. NH2 is the leaving group and CH3OH is the nucleophile

D. CH3COO- is the leaving group and CH3NH2 is the nucleophile.

Among the acid derivatives, acid halide is more reactive towards substitution reaction followed by anhydride then ester then acid and finally amide (least reactive due to resonance in amide from lone pair of electrons on nitrogen).

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