Which of these compounds could not be formed by nucleophilic attack by an appropriate reagent on acetyl chloride? A)CH₃CONH₂ B)CH₃CO₂CH₂CH₃ C)ClCH₂COCl D)CH₃CO₂H E)(CH₃CO)₂O

Question

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Acetyl chloride has a highly electrophilic carbonyl carbon due to the electron-withdrawing effect of the chlorine atom. Nucleophilic attack can occur on this carbon, resulting in substitution of the chlorine atom. However, option C already has two chlorine atoms attached to the carbonyl carbon, making it impossible for further nucleophilic attack to occur. The other options do not have this issue and can be formed by nucleophilic attack.

Which of These Compounds Could Not Be Formed by Nucleophilic