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Compounds Containing Nitrogen question

2024 · 29 Jan · Shift 2 · Q13
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Compounds Containing Nitrogen question

2024 · 29 Jan · Shift 2 · Q13

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which of the following reaction is correct?
  1. A
    C2H5CONH2+Br2+NaOH→C2H5CH2NH2+Na2CO3+NaBr+H2O\mathrm{C}_2 \mathrm{H}_5 \mathrm{CONH}_2+\mathrm{Br}_2+\mathrm{NaOH} \rightarrow \mathrm{C}_2 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{NH}_2+\mathrm{Na}_2 \mathrm{CO}_3+\mathrm{NaBr}+\mathrm{H}_2 \mathrm{O}C2​H5​CONH2​+Br2​+NaOH→C2​H5​CH2​NH2​+Na2​CO3​+NaBr+H2​O
  2. B
    JEE Main 2024 (Online) 29th January Evening Shift Chemistry - Compounds Containing Nitrogen Question 42 English Option 2
  3. C
    JEE Main 2024 (Online) 29th January Evening Shift Chemistry - Compounds Containing Nitrogen Question 42 English Option 3
  4. D
    CH3CH2CH2NH2→H2OHNO2,0∘CCH3CH2OH+N2+HCl\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{NH}_2 \xrightarrow[\mathrm{H}_2 \mathrm{O}]{\mathrm{HNO}_2, 0^{\circ} \mathrm{C}} \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{OH}+\mathrm{N}_2+\mathrm{HCl}CH3​CH2​CH2​NH2​HNO2​,0∘CH2​O​CH3​CH2​OH+N2​+HCl
View written solutionFree

Correct answer: C

  1. Identify the reactions involved

    We inspect the given visible options.

    • Option A shows an amide reacting with Br2/NaOH\mathrm{Br_2/NaOH}Br2​/NaOH.
    • Option D shows a primary aliphatic amine reacting with nitrous acid at 0∘C0^\circ\mathrm{C}0∘C.
  2. Check Option A

    The substrate is propanamide: C2H5CONH2=CH3CH2CONH2\mathrm{C_2H_5CONH_2} = \mathrm{CH_3CH_2CONH_2}C2​H5​CONH2​=CH3​CH2​CONH2​

    With Br2/NaOH\mathrm{Br_2/NaOH}Br2​/NaOH, amides undergo Hofmann bromamide degradation: RCONH2→Br2/NaOHRNH2\mathrm{RCONH_2} \xrightarrow{Br_2/NaOH} \mathrm{RNH_2}RCONH2​Br2​/NaOH​RNH2​ with loss of one carbon atom.

    So, C2H5CONH2→C2H5NH2\mathrm{C_2H_5CONH_2} \to \mathrm{C_2H_5NH_2}C2​H5​CONH2​→C2​H5​NH2​ i.e. the product should be ethylamine, not propylamine.

    But option A gives: C2H5CH2NH2\mathrm{C_2H_5CH_2NH_2}C2​H5​CH2​NH2​ which is propylamine.

    Therefore, Option A is incorrect.

  3. Check Option D

    The reactant is propylamine: CH3CH2CH2NH2\mathrm{CH_3CH_2CH_2NH_2}CH3​CH2​CH2​NH2​

    Primary aliphatic amines with nitrous acid give alcohols: RNH2+HNO2→ROH+N2+H2O\mathrm{RNH_2 + HNO_2 \to ROH + N_2 + H_2O}RNH2​+HNO2​→ROH+N2​+H2​O

    Thus propylamine should give 1-propanol: CH3CH2CH2OH\mathrm{CH_3CH_2CH_2OH}CH3​CH2​CH2​OH

    But option D gives: CH3CH2OH\mathrm{CH_3CH_2OH}CH3​CH2​OH which is ethanol, having one carbon less.

    Hence, Option D is incorrect.

  4. Conclusion

    Since A and D are wrong, the correct reaction must be the remaining valid option among the unseen choices. The stored correct answer is C, which is consistent with elimination of A and D.

    Therefore, the correct answer is: C\boxed{C}C​

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