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Which of the following is most reactive in nucleophilic acyl substitution?Select answer from the options belowacid halideketoneestercarboxylic acid

Question

Which of the following is most reactive in nucleophilic acyl substitution?

Select answer from the options below:

  • acid halide
  • ketone
  • ester
  • carboxylic acid
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Solution

Analysis of Reactivity in Nucleophilic Acyl Substitution

  1. Understanding Nucleophilic Acyl Substitution: Nucleophilic acyl substitution is a reaction in which a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. The reactivity of the acyl compound largely depends on the nature of the electron-withdrawing or electron-donating groups attached to the carbonyl.

  2. Comparison of Functional Groups:

    • Acid Halides: These are highly reactive towards nucleophiles due to the presence of a good leaving group (the halide) and the electron-withdrawing nature of the halogen.
    • Ketones: Ketones are less reactive than acid halides because they have two alkyl groups that donate electron density to the carbonyl carbon, making it less electrophilic.
    • Esters: Esters are moderate in reactivity. While they have a relatively good leaving group (alkoxide), their electron-donating alkyl groups make them less reactive than acid halides.
    • Carboxylic Acids: These have poor reactivity due to the presence of a hydroxyl group, which is a poor leaving group in nucleophilic substitution reactions.
  3. Conclusion: Among the given options, acid halides are the most reactive in nucleophilic acyl substitution due to the strong electrophilic character of the carbonyl carbon and the ability of the halide to leave easily. Thus, the correct answer is:

Final Answer

Acid halide

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