Hydrocarbon (A), C_6H_10 on treatment with H_2//Ni,H_2/Lindler catalyst and Na /Liquid ammonia forms three different reduction products (B), (C) and (C) respectively. (A) does not form any salt with ammoniacal AgNO_3 solution, but forms a salt(E) on heating with NaNH_2 in an intert solvent. Compound (E) reacts with CH_3I to give (F). Compound (D) on oxidative ozonolysis gives n-butanoic acid along with other product. Give structurs of (A) to (F) with proper reasoning .

Hydrocarbon (A), C_6H_10 on treatment with H_2//Ni,H_2/Lindler catalys

1.	Hydrocarbon (A), C_6H_10 on treatment with H_2//Ni,H_2/Lindler catalyst and Na /Liquid ammonia forms three different reduction products (B), (C) and (C) respectively. (A) does not form any salt with ammoniacal AgNO_3 solution, but forms a salt(E) on heating with NaNH_2 in an intert solvent. Compound (E) reacts with CH_3I to give (F). Compound (D) on oxidative ozonolysis gives n-butanoic acid along with other product. Give structurs of (A) to (F) with proper reasoning .
Answer» Solution :(i) The given compound (A) is confirmed by the following reactions. (ii) A does not FORM any SALT with ammonical `AgNO_3` solution , but forms a salt (E) on heating with `NaNH_2`in an inert SOLVENT. `underset((A)"Hex-2-yne")(CH_3CH_2 CH_2-C-=C-CH_3)overset(NaNH_2)tounderset((E))(CH_3CH_2CH_2CH_2)-C-=CNa overset(CH_3I)tounderset((F))(CH_3CH_2CH_2CH_2-C-=C-CH_3` (iii) Oxidative oxonolysis of (D) gives `CH_3CH_2CH_2CH_2COOH` ALONG with `CH_3COOH`.