An organic compound X having molecular formula `C_4H_11N` reacts with p-toluene sulphonyl chloride to form a compound Ythat is soluble in aqueous KOH. Compound X is optically active and reacts with acetyl chloride to form compound Z. Identify the compound Z.

Options

A. `CH_3CH_2CH_2CH_2NHCOCH_3`
B. `CH_3CH_2 oversetoverset(CH_3)|C NH HCOCH_3`
C. `CH_3 overset(CH_3)overset|C HC H_2NHCOCH_3`
D. `CH_3-undersetunderset(CH_3)|oversetoverset(CH_3)|C-NHCOCH_3`

Answer

B

Explanation

Since, `X(C_4H_11N)` reacts with p-toluene sulphonyl chloride (Hinsberg reagent) to form a compound which is soluble in KOH, therefore X must be a primary amine.
`undersetX(C_6H_5SO_2Cl+H-oversetoversetH|N-overset(CH_3)overset|undersetHunderset|C-CH_2-CH_3) underset(-HCl)to underset"(Soluble in KOH)"undersetY((C_6H_5SO_2-oversetoverset(H)|N-undersetundersetH|oversetoverset(CH_3)|C-CH_2-CH_3))`
`undersetX(CH_3-CH_2-oversetoverset(CH_3)|CH-oversetoversetH|N-H+ClCOCH_3 underset(-HCl)) to undersetZ(CH_3-CH_2-oversetoverset(CH_3)|CH-NHCOCH_3)`