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Compounds Containing Nitrogen question

2021 · 17 Mar · Shift 1 · Q3
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Compounds Containing Nitrogen question

2021 · 17 Mar · Shift 1 · Q3

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Hoffmann bromomide degradation of benzamide gives product A, which upon heating with CHCl3CHCl_3CHCl3​ and NaOHNaOHNaOH gives product B. The structures of A and B are :
  1. A
    JEE Main 2021 (Online) 17th March Morning Shift Chemistry - Compounds Containing Nitrogen Question 148 English Option 1
  2. B
    JEE Main 2021 (Online) 17th March Morning Shift Chemistry - Compounds Containing Nitrogen Question 148 English Option 2
  3. C
    JEE Main 2021 (Online) 17th March Morning Shift Chemistry - Compounds Containing Nitrogen Question 148 English Option 3
  4. D
    JEE Main 2021 (Online) 17th March Morning Shift Chemistry - Compounds Containing Nitrogen Question 148 English Option 4
View written solutionFree

Correct answer: A

  1. Hofmann bromamide degradation of benzamide

Benzamide is C6H5CONH2C_6H_5CONH_2C6​H5​CONH2​.

In Hofmann bromamide degradation, an amide on treatment with Br2/NaOHBr_2/NaOHBr2​/NaOH gives a primary amine with one carbon less:

RCONH2→Br2/NaOHRNH2RCONH_2 \xrightarrow{Br_2/NaOH} RNH_2RCONH2​Br2​/NaOH​RNH2​

So,

C6H5CONH2→Hofmann degradationC6H5NH2C_6H_5CONH_2 \xrightarrow{Hofmann\ degradation} C_6H_5NH_2C6​H5​CONH2​Hofmann degradation​C6​H5​NH2​

Thus, product AAA is aniline.


  1. Reaction of product A with CHCl3CHCl_3CHCl3​ and NaOHNaOHNaOH

Aniline is a primary amine. Primary amines on heating with chloroform and alcoholic sodium hydroxide give isocyanides. This is the carbylamine reaction:

RNH2+CHCl3+3NaOH→RNC+3NaCl+3H2ORNH_2 + CHCl_3 + 3NaOH \rightarrow RNC + 3NaCl + 3H_2ORNH2​+CHCl3​+3NaOH→RNC+3NaCl+3H2​O

For aniline:

C6H5NH2→ΔCHCl3,NaOHC6H5NCC_6H_5NH_2 \xrightarrow[\Delta]{CHCl_3,NaOH} C_6H_5NCC6​H5​NH2​CHCl3​,NaOHΔ​C6​H5​NC

So, product BBB is phenyl isocyanide (isocyanobenzene).


  1. Identify structures of A and B
  • A=A = A= aniline, C6H5NH2C_6H_5NH_2C6​H5​NH2​
  • B=B = B= phenyl isocyanide, C6H5NCC_6H_5NCC6​H5​NC

So the correct option is the one showing:

A=C6H5NH2,B=C6H5NCA = C_6H_5NH_2, \quad B = C_6H_5NCA=C6​H5​NH2​,B=C6​H5​NC


  1. Comparison with stored correct answer

Stored correct answer: A

Our derived answer is also A.

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