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Aldehydes, Ketones and Carboxylic Acids

Short Answer Type

321.

Explain the mechanism of aldol condensation using ethanal as an example.

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322.

Account for the following:
Carboxylic acids with five or less carbons are water soluble, but many with six or more carbons dissolves in alcohols.

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323.

Account for the following:
Carboxylic acids exist as dimers in the vapour phase.

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324. Illustrate the mechanism of reaction of carbonyl group with an ammonia derivative, H₂N—Z.

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325. Account for the fact that the C—O bond in RCOOH is shorter than in ROH ?

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326. Compare the reactivities of the C = O in RCOOH and RCHO towards nucleophiles.

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Long Answer Type

327. Why is benzoic acid a stronger acid than phenol?

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Short Answer Type

328. Write equation for the ionization of RCOOH and for K_a and then explain why RCOOH has a lower pKa value than alcohol.

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329. Account for the following acidic strength order:

$FCH subscript 2 COOH space space space space space greater than space space space space ClCH subscript 2 COOH space space space greater than space space BrCH subscript 2 COOH space space greater than space space ICH subscript 2 COOH space greater than space CH subscript 3 COOH$

Size of atom down the group decreases thus, the electron-withdrawing power of the halogen decreases, the stability of the conjugate base also decreases. Hence, the acidic strength decreases as we move from FCH₂COOH to CH₃COOH.

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330. Account for the following acidic strength order:

Cl subscript 3 straight C space COOH greater than space Cl subscript 2 CHCOOH greater than ClCH subscript 2 COOH space greater than CH subscript 3 COOH

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