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Compounds Containing Nitrogen question

2013 · Shift 0 · Q4
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Compounds Containing Nitrogen question

2013 · Shift 0 · Q4

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
An organic compound A upon reacting with NH3N{H_3}NH3​ gives B.B.B. On heating BBB gives C.CC.CC.C in presence of KOHKOHKOH reacts with Br2B{r_2}Br2​ to given CH3CH2NH22.AC{H_3}C{H_2}N{H_2}2.ACH3​CH2​NH2​2.A is :
  1. A
    CH3COOHC{H_3}COOHCH3​COOH
  2. B
    CH3CH2CH2COOHC{H_3}C{H_2}C{H_2}COOHCH3​CH2​CH2​COOH
  3. C
    JEE Main 2013 (Offline) Chemistry - Compounds Containing Nitrogen Question 211 English Option 3
  4. D
    CH3CH2COOHC{H_3}C{H_2}COOHCH3​CH2​COOH
View written solutionFree

Correct answer: D

  1. Identify the final reaction

The compound CCC reacts with Br2/KOHBr_2/KOHBr2​/KOH to give CH3CH2NH2CH_3CH_2NH_2CH3​CH2​NH2​.

This is the Hofmann bromamide reaction:

RCONH2→Br2/KOHRNH2RCONH_2 \xrightarrow{Br_2/KOH} RNH_2RCONH2​Br2​/KOH​RNH2​

with loss of one carbon atom from the amide.

Since the product amine is:

CH3CH2NH2CH_3CH_2NH_2CH3​CH2​NH2​

CCC must be the amide having one extra carbon:

C=CH3CH2CONH2C = CH_3CH_2CONH_2C=CH3​CH2​CONH2​

which is propanamide.


  1. Relate BBB and CCC

Given that on heating BBB gives CCC.

A carboxylic acid reacts with ammonia to first form the ammonium salt, which on heating gives the amide:

RCOOH+NH3→RCOO−NH4+  (B)RCOOH + NH_3 \rightarrow RCOO^-NH_4^+ \;(B)RCOOH+NH3​→RCOO−NH4+​(B)

On heating:

RCOO−NH4+→ΔRCONH2  (C)+H2ORCOO^-NH_4^+ \xrightarrow{\Delta} RCONH_2 \;(C) + H_2ORCOO−NH4+​Δ​RCONH2​(C)+H2​O

So if

C=CH3CH2CONH2C = CH_3CH_2CONH_2C=CH3​CH2​CONH2​

then BBB must be ammonium propanoate:

B=CH3CH2COO−NH4+B = CH_3CH_2COO^-NH_4^+B=CH3​CH2​COO−NH4+​


  1. Find AAA

Since AAA reacts with NH3NH_3NH3​ to give BBB, AAA must be the corresponding carboxylic acid:

A=CH3CH2COOHA = CH_3CH_2COOHA=CH3​CH2​COOH

This is propanoic acid.


  1. Check with options
  • A: CH3COOHCH_3COOHCH3​COOH gives acetamide, which on Hofmann degradation gives CH3NH2CH_3NH_2CH3​NH2​, not CH3CH2NH2CH_3CH_2NH_2CH3​CH2​NH2​.
  • B: CH3CH2CH2COOHCH_3CH_2CH_2COOHCH3​CH2​CH2​COOH gives butanamide, which on Hofmann degradation gives CH3CH2CH2NH2CH_3CH_2CH_2NH_2CH3​CH2​CH2​NH2​.
  • D: CH3CH2COOHCH_3CH_2COOHCH3​CH2​COOH gives propanamide, which on Hofmann degradation gives CH3CH2NH2CH_3CH_2NH_2CH3​CH2​NH2​.

Hence the correct option is:

D  :  CH3CH2COOH\boxed{D}\;:\; CH_3CH_2COOHD​:CH3​CH2​COOH

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