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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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Solution :
(i) cross aldol condensation - Aldol condensation between two aldehydes or two ketones or between one aldehyde and ketone is known as cross aldol condensation .
(ii) Decarboxylation - The Process of removal of a molecule of$CO_2$ from a carboxylic acid is called decarboxylation .
It is carried out by heating a carboxylic acid or its salt with sodalime at $600^{\circ}C$
(i) Pentan - 2-one and pentan -3-one - The two compound
$CH_3COCH_2CH_2CH_3+3NaOl \to CH_3CH_2CH_2COONa +2NaOH +CHI_3$
$CH_3CH_2COCH_2CH_3+3 NaOl \to $ No formation of yellow ppt
(ii) Benzaldehyde and acetophenone - The two compounds can be distinguished by performing iodoform test .
Acetophenone will give the yellow ppt of iodoform while benzaldehyde will not give any ppt .
$C_6H_5COCH_3 +3 NaOH \to C_6 H_5 COONa +2NaOH +CHI_3$
(iii) Phenol and benzoic acid - Add neutral ferric chloride phenol will form form a violet color while benzoic acid will not .
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