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(a) Illustrate the following reactions giving a suitable example for each:
(i) Cross aldol condensation
(ii) Decarboxylation
(b) Give simple tests to distinguish between the following pairs of compounds
(i) Pentan-2-one and Pentan-3-one
(ii) Benzaldehyde and Acetophenone
(iii) Phenol and Benzoic acid

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(a) (i) When aldol condensation is carried out between two different aldehydes and/or ketones, it is called cross aldol condensation.

(ii) Sodium salt of carboxylic acids on heating with soda lime lose carbon dioxide and form hydrocarbons. This reaction is called decarboxylation.

(b) (i) Pentan-2-one when treated with NaOI (I2 /NaOH) gives yellow precipitate of iodoform but pentan-3-one does not give this test.

(ii) Benzaldehyde being an aldehyde gives silver mirror with Tollen’s reagent but acetophenone being a ketone does not give this test.

(iii) Benzoic acid produces brisk effervescence with sodium bicarbonate solution while phenol does not.

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