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    Home » Explain: C—O bond length in RCOOH is shorter

    Explain: C—O bond length in RCOOH is shorter

    Dr. Vikas JasrotiaBy Dr. Vikas JasrotiaNovember 12, 2021No Comments
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    C—O bond length in RCOOH

    Que. Explain the following giving proper reasoning:

    (a) C—O bond length in RCOOH is shorter than in ROH

    (b) Highly branched carboxylic acids are less acidic than unbranched acids

    Ans. (a) RCOOH has the following resonance structure

    Because of the contribution of structure (b), there is some double-bond character in the C—O bond of the acid. Therefore C—O bond length is shorter than R—OH which has a pure single bond character.

    (b) The carboxylate ion (RCOO–) of branched-chain acids is shielded from solvent molecules and can not be stabilized by solvation as effectively as the carboxylate ion of unbranched acids. Simultaneously branched-chain alkyl group causes a more electron-donating effect than an unbranched chain, hence decreasing the acidic nature of carboxylic acid.

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