Question:

Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride?

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Cyclic anhydrides form easily only when a 5- or 6-membered ring results; count the ring size of each possible anhydride.
Updated On: Nov 5, 2026
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The Correct Option is A

Solution and Explanation

Option (1) is the open-chain acid \(\mathrm{HOOC-(CH_2)_4-COOH}\) (adipic acid, drawn in a curled shape). Its anhydride would be a 7-membered ring, which is unfavourable.
Option (2) phthalic acid gives a 5-membered cyclic anhydride (phthalic anhydride) readily.
Option (3) succinic acid \(\mathrm{HOOC-CH_2-CH_2-COOH}\) gives a 5-membered anhydride (succinic anhydride).
Option (4) cyclopentane-1,2-dicarboxylic acid (adjacent groups) gives a fused 5-membered anhydride.
So the acid least reactive towards anhydride formation is adipic acid.
Answer: (1) the open-chain hexanedioic (adipic) acid
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