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Compounds Containing Nitrogen question

2019 · 11 Jan · Shift 2 · Q14
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Compounds Containing Nitrogen question

2019 · 11 Jan · Shift 2 · Q14

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
A compound 'X' on treatment with Br2Br_2Br2​/NaOHNaOHNaOH, provided C3H9NC_3H_9NC3​H9​N, which gives positive carbylamine test. Compound 'X' is :
  1. A
    CH3CH2CH2CONH2CH_3CH_2CH_2CONH_2CH3​CH2​CH2​CONH2​
  2. B
    CH3CON(CH3)2CH_3CON(CH_3)_2CH3​CON(CH3​)2​
  3. C
    CH3CH2COCH2NHCH_3CH_2COCH_2NHCH3​CH2​COCH2​NH
  4. D
    CH3COCH2NHCH3CH_3COCH_2NHCH_3CH3​COCH2​NHCH3​
View written solutionFree

Correct answer: A

  1. The reagent Br2/NaOHBr_2/NaOHBr2​/NaOH indicates the Hofmann bromamide reaction.

    In this reaction, an amide of type RCONH2→Br2/NaOHRNH2RCONH_2 \xrightarrow{Br_2/NaOH} RNH_2RCONH2​Br2​/NaOH​RNH2​ gives a primary amine with one carbon less.

  2. The product formed is given as having molecular formula C3H9NC_3H_9NC3​H9​N and it gives a positive carbylamine test.

    • Carbylamine test is given only by primary amines.
    • A primary amine with formula C3H9NC_3H_9NC3​H9​N is propylamine (C3H7NH2)(C_3H_7NH_2)(C3​H7​NH2​).

    Therefore, the Hofmann reaction product must be a 3-carbon primary amine.

  3. Hence the starting amide must have 4 carbons and be of the form: C3H7CONH2C_3H_7CONH_2C3​H7​CONH2​

  4. Now check the options:

    A. CH3CH2CH2CONH2CH_3CH_2CH_2CONH_2CH3​CH2​CH2​CONH2​

    • This is butanamide.
    • On Hofmann bromamide degradation: CH3CH2CH2CONH2→Br2/NaOHCH3CH2CH2NH2CH_3CH_2CH_2CONH_2 \xrightarrow{Br_2/NaOH} CH_3CH_2CH_2NH_2CH3​CH2​CH2​CONH2​Br2​/NaOH​CH3​CH2​CH2​NH2​
    • Product is propylamine, formula C3H9NC_3H_9NC3​H9​N, a primary amine.
    • Gives positive carbylamine test. ✅

    B. CH3CON(CH3)2CH_3CON(CH_3)_2CH3​CON(CH3​)2​

    • This is a tertiary amide (no −CONH2-CONH_2−CONH2​ group).
    • Hofmann bromamide reaction requires a primary amide.
    • So this will not give the required primary amine. ❌

    C. CH3CH2COCH2NHCH_3CH_2COCH_2NHCH3​CH2​COCH2​NH

    • This is not a proper primary amide structure for Hofmann degradation. ❌

    D. CH3COCH2NHCH3CH_3COCH_2NHCH_3CH3​COCH2​NHCH3​

    • Also not a primary amide. ❌
  5. Therefore, the only suitable compound is: CH3CH2CH2CONH2\boxed{CH_3CH_2CH_2CONH_2}CH3​CH2​CH2​CONH2​​

So, option A is correct.

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