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NEET CHEMISTRYMedium

Which of the following does not give nucleophilic substitution with alcohol?

A

CH₃COCl

B

Acetic anhydride

C

Ether

D

None of the above

Step-by-Step Solution

Alcohols (ROHR-OH) act as nucleophiles due to the presence of lone pairs on the oxygen atom. They undergo nucleophilic acyl substitution reactions with acid derivatives like Acid Chlorides (CH3COClCH_3COCl) and Acid Anhydrides ((CH3CO)2O(CH_3CO)_2O) to form esters.

  1. With CH3COClCH_3COCl: ROH+CH3COClCH3COOR+HClR-OH + CH_3COCl \rightarrow CH_3COOR + HCl (Vigorous reaction).
  2. With Acetic Anhydride: ROH+(CH3CO)2OCH3COOR+CH3COOHR-OH + (CH_3CO)_2O \rightarrow CH_3COOR + CH_3COOH (Reaction occurs in presence of acid/base).
  3. With Ether: Ethers (RORR-O-R') are quite stable towards nucleophilic attack because the alkoxide ion (RORO^-) is a poor leaving group. Therefore, alcohols do not react with ethers via nucleophilic substitution under standard conditions.

Thus, Ether is the compound that does not give nucleophilic substitution with alcohol.

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