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(a) Compound A (C(8)H(8)O)on treatment w...

(a) Compound A `(C_(8)H_(8)O)`on treatment with `NH_(2)`OH. HCI gives B and C. B and C rearrange to give D and E, respectively on treatement with acid. B, C, D and E are all isomers of moleculare formula `(C_(8)H_(9)N)` When D is boiled with alcohol KOH an oil F `(C_(6)H_(7)N)` separates out F, reacts rapidly with `CH_(3)` COOI to give back D. On the other hand. E on boiling with alkali followed by acidification gives a white solid G`(C_(7)H_(6)O_(2))`. Identify `A-G`
(b) Carry out the following transformation in not more than three steps. `1`-butyne "to" `2`-pentanone

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Compound (A) (C_(8)H_(8)O) on treatment with NH_(2)OH.HCl gives (B) and (C ). (B) and (C ) rearrange to give (D) and E, respectively, on treatment with acid. (B), (C ), (D), and (E ) are all isomers of molecular formula (C_(8)H_(9)NO) . When (D) is boiled with alcoholic KOH, an oil (F) (C_(6)H_(7)N) separates out. (F) reacts rapidly with CH_(3)COCl to give back (D). On the other hand, (E ) on boiling with alkali followed by acidification gives a white solid (G) (C_(7)H_(6)O_(2)) . Identify (A) to (G).

A compound D(C_(8)H_(10)O) upon treatement with alkaline solution of iodine gives a yellow precipitate. The fibtrate on acidification gives a white solid E(C_(7)H_(6)O_(2)) . Write the structures of D,E and explain the formation of E.

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