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Question 57

Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above reaction is:

Solution

Ethanoyl chloride is an acyl chloride, $$CH_3COCl$$. Acyl chlorides undergo nucleophilic acyl-substitution reactions very readily.

Step 1 (identify the nucleophile): Sodium ethoxide is $$NaOCH_2CH_3$$. In solution it gives the strong nucleophile/strong base $$\;^-OCH_2CH_3$$ (ethoxide ion).

Step 2 (write the reaction):
$$CH_3COCl + \;^-OCH_2CH_3 \;\longrightarrow\; CH_3COOCH_2CH_3 + Cl^-$$

Step 3 (mechanism outline):
• The ethoxide ion attacks the electrophilic carbonyl carbon of $$CH_3COCl$$, forming a tetrahedral intermediate.
• The leaving group $$Cl^-$$ departs, restoring the carbonyl and giving the ester $$CH_3COOCH_2CH_3$$ (ethyl ethanoate).
• Sodium ion pairs with chloride ion to give the by-product $$NaCl$$.

Because an acyl chloride plus an alkoxide (or alcohol) always furnishes an ester, the product here must be the ester derived from ethanoyl chloride and ethanol/ethoxide, namely ethyl ethanoate.

The other options do not come from this reaction pathway:
• 2-Butanone (Option A) is a ketone, not formed in nucleophilic substitution of acyl chlorides.
• Ethyl chloride (Option B) would require substitution at ethoxide oxygen by chloride, which is not favored.
• Diethyl ether (Option D) comes from dehydration of ethanol, not from reaction with an acyl chloride.

Hence the product is ethyl ethanoate.

Option C which is: Ethyl ethanoate

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