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Compounds Containing Nitrogen question

2023 · 31 Jan · Shift 2 · Q4

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Chemistry
Compounds Containing Nitrogen
2023 · 31 Jan · Shift 2 · Q4

Compounds Containing Nitrogen question

2023 · 31 Jan · Shift 2 · Q4

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1

An organic compound

[\mathrm{A}]\left(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\right)

, shows optical activity and gives

\mathrm{N}_{2}

gas on treatment with

\mathrm{HNO}_{2}

. The compound

[\mathrm{A}]

reacts with

\mathrm{PhSO}_{2} \mathrm{Cl}

producing a compound which is soluble in

\mathrm{KOH}

. The structure of

\mathrm{A}

is :

A
B
C
D

View written solutionFree

Correct answer: B

From reaction with $\mathrm{HNO_2}$
A primary aliphatic amine reacts with nitrous acid to give alcohol with evolution of nitrogen gas:

\mathrm{RNH_2 + HNO_2 \rightarrow ROH + N_2 + H_2O}

So, $[A]$ must be a 1° amine.

From Hinsberg test
$[A]$ reacts with $\mathrm{PhSO_2Cl}$ to give a product soluble in $\mathrm{KOH}$ . This is characteristic of a primary amine, because the sulfonamide formed contains an acidic N–H and dissolves in alkali.

So again, $[A]$ is confirmed as a primary amine.

Molecular formula analysis
Given formula is $\mathrm{C_4H_{11}N}$ . Possible primary amines are:

butan-1-amine: $\mathrm{CH_3CH_2CH_2CH_2NH_2}$
butan-2-amine: $\mathrm{CH_3CH(NH_2)CH_2CH_3}$
2-methylpropan-1-amine: $(\mathrm{CH_3})_2\mathrm{CHCH_2NH_2}$
2-methylpropan-2-amine: $(\mathrm{CH_3})_3\mathrm{CNH_2}$

Optical activity condition
For optical activity, the molecule must contain a chiral carbon atom.

butan-1-amine: no chiral center
butan-2-amine: carbon-2 is attached to $\mathrm{NH_2}$ , $\mathrm{H}$ , $\mathrm{CH_3}$ , and $\mathrm{C_2H_5}$ → four different groups, so chiral
2-methylpropan-1-amine: no chiral center
2-methylpropan-2-amine: central carbon has three identical $\mathrm{CH_3}$ groups, so achiral

Thus, the only structure satisfying all conditions is:

\mathrm{CH_3-CH(NH_2)-CH_2-CH_3}

which is butan-2-amine (sec-butylamine).

Comparison with stored answer
Derived answer is Option B. This matches the stored correct answer.

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