(a) An organic compound (A) has characteristic odour . On treatment with NaOH it forms two compounds (B) and (C ) compound (B ) has molecular formula `C_7 H_8 O` which on oxidation gives back (A ) . The compound (C ) is a sodium salt of an acid. When (C) is treated with soda lime it yields an aromatic hydrocarbon (D).Deduce the structures of (A ) ,(B ) , (C ) and (D ) write the sequence of reactions involved .
(b) complete each synthesis by filling the missing starting materials reagents or products (x,y and z )
(i) `C_6 H_5 CHO +CH_3 CH_2 CHO overset(NaOH ) to X `
(ii) `CH_3 (CH_2) _9 COOC _2 H_5 overset(Z)to CH_3 (CH_2) _9 CHO`
(c) How will you bring about the following conversions in not more than two steps
(i) Toluene to benzaldehyde
(ii) Ethylcyanide to 1- Phenylpropanone .

Explanation

(a) the compound A is `C_6 H_5 CHO ` benzaldehyde having charcteristic odour the reactions are :
` C_6 H_5 CHO overset(NaOH) to underset((B ))(C_6H_5 CH_2OH) +C_6 H_5 COONa `
` C_6 H_5 CH_2 OH overset( O ) to C_6 H_5 CHO `
`C_6 H_5 COONa overset( NaOH //CaO ) to C_6 H_6 `
` A: C_6 H_5 CH_2 OH , C =C_6 COONa , D : C_6 H_6 `
( b) (i ) `C_6 H_5 CHO +CH_3 CH_2 CHO overset(NaOH) to C_6 H_5 - underset(OH) underset(|) CH- underset(CH_3) underset(|)CH-CHO`
`(ii) CH_3 (CH_2) CH_9 COOC_2 H_5 underset(-78 ^@ C ) overset(DIBALH //H_2O) to CH_3(CH_2)_9 CHO`