1.

(a) Write the chemical reaction involved in Wolff-Kishan reduction. (b) Arrange the following in the increasing order on their reactivity towards nucleophilic addition reaction : C_(6) H_(5) COCH_(3) , CH_(3) - CHO, CH_(3) COCH_(3) (c ) Why carboxylic acid does not give reactions of carbonyl group ? (d) Write the product in the following reaction : CH_(3) CH_(2) CH = CH - CH_(2) CN underset(2. H_(2)O ) overset( 1.(i-Bu)_(2) AlH) (rarr) (e ) A and B are two functional isomers of compound C_(3) H_(6) O. On heating with NaOH AND i_(2), isomer B forms yellow precipitate of iodoform whereas isomer A does not form any precipitate. Write the formulae of A and B.

Answer»

Solution :(a) Wolff - Kishner reduction `:`

(b) Increasing order of reactivity towards nucleophilic addition reaction
`C_(6) H_(5) COCH_(3) lt CH_(3) COCH_(3) lt CH_(3) CHO`
(C ) Carboxylic acid does not give reactions of carbonyl group `:`

Carboxyl CARBON is not able to get a positive charge because of the resonating structure of carboxylate ion. Without a positive charge, nucelophilic addition reaction of carbonyl compound is not possible.
(d) `CH_(3)CH_(2)CH = CH -CH_(2) CN underset(2.H_(2)O)overset(1.(i-Bu)_(2)AlH)(RARR) CH_(3) CH_(2) CH = CH - CH_(2) - CHO`
(e ) The formula (structure) of `A = CH_(2) = CH - CH_(2) OH ` or `CH_(2) = CH - O - CH_(3)` structure of B `= CH_(3) COCH_(3)`
A compound containing `CH_(3) CO^(-)` group gives iodoform test with NaOH and `I_(2)`.


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