IIT-JEE 2011 · Paper 2 · Chemistry Q12

ChemistryMultiple correct+4Question 12 of 60

The correct functional group X and the reagent/reaction conditions Y in the following scheme are

X =

\ce{COOCH3}

, Y =

\ce{H2}

/Ni/heat

X =

\ce{CONH2}

, Y =

\ce{H2}

/Ni/heat

X =

\ce{CONH2}

, Y =

\ce{Br2}

/NaOH

X = CN, Y =

\ce{H2}

/Ni/heat

Answer and worked solution

Official answer: C, D

Need: a diamine $\ce{H2N-R-NH2}$ to condense with adipic acid into a polyamide.

(C) Hofmann bromamide: $\ce{H2NOC(CH2)4CONH2 ->[Br2/NaOH] H2N(CH2)4NH2}$ , giving nylon-4,6. ✓
(D) $\ce{NC(CH2)4CN ->[H2/Ni] H2N(CH2)6NH2}$ , giving nylon-6,6. ✓
(B) $\ce{H2}$ /Ni does not reduce amides to amines.
(A) An ester does not become an amine.

(C), (D)

Topics:Amines

IIT-JEE 2011 · Paper 2, Chemistry question 12