An organic compound [A] `C_(6)H_(10)`, on reduction first gives [B] `C_(6)H_(12)`, and finally [C] `C_(6)H_(14)`. [A] on ozonolysis followed by hydrolysis gives two aldehydes [D] `C_(2)H_(4)O`, and [E] `C_(2)H_(2)O`. Oxidation of [B] with acidified `KMnO_(4)` gives acid [F] `C_(4)H_(8)O_(2)`. Determine the structures of the compounds [A] to [F] with proper reasoning.

Explanation

(i)Since the aldehyde (E) contains two O atoms , therefore, it must be a dialdehyde. The only dialdehyde having the molecular formula , `C_2H_2O_2` is glyoxal, i.e., O=CH-CH=O . The other aldehyde (D) having the molecular formula , `C_2H_4O` must be acetaldehyde, i.e., `CH_3CHO`. Further since glyoxal is a dialdehyde therefore, two molecules of acetaldehyde must have been formed . Thus, the structure of the alkene (A) is `underset"Hexa-2,4-diene(A)"(CH_3CH=CH-CHCH_3)underset((ii)Zn//H_2O)overset((i)O_3//CH_2Cl_2)to underset"Acetaldehyde"(CH_3CH)=O+O = underset"Glyoxal"(CH-CH)=O+O =underset"Acetaldehyde"(CHCH_3)`
(ii)Since, (A) on reduction gives (B) which on oxidation with alk. `KMnO_4` gives only the acid (F), therefore (B) must be hex-3-ene and (F) must be propanoic acid
`underset"[A]"(CH_3CH=CH-CH=CHCH_3)underset"1,4-Addition"overset(H_2//Ni)to underset"Hex-3-ene(B)"(CH_3CH_2CH=CHCH_2CH_3)overset"[O]"to underset"Propanoic acid (F)"(CH_3CH_2COOH)+ underset"Propanoic acid(F)"(CH_3CH_2COOH)`
(iii)Since (A) on reduction first gives B (hex-3-ene) and finally (C ) , therefore , (C) must be n-hexane.
`underset"Hex-3-ene"(CH_3CH_2CH=CHCH_2CH_3)overset(H_2//Ni)to underset"n-Hexane(C)"(CH_3CH_2CH_2CH_2CH_2CH_3)`