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Compounds Containing Nitrogen question

2021 · 27 Jul · Shift 1 · Q4
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  5. /2021 · 27 Jul · Shift 1 · Q4

Compounds Containing Nitrogen question

2021 · 27 Jul · Shift 1 · Q4

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Given below are two statements : Statement I : Aniline is less basic than acetamide. Statement II : In aniline, the lone pair of electrons on nitrogen atom is delocalized over benzene ring due to resonance and hence less available to a proton. Choose the most appropriate option;
  1. A
    Statement I is true but statement II is false.
  2. B
    Statement I is false but statement II is true.
  3. C
    Both statement I and statement II are true.
  4. D
    Both statement I and statement II are false.
View written solutionFree

Correct answer: B

  1. Check Statement I: "Aniline is less basic than acetamide."

    We compare the basic strength of aniline and acetamide.

    • In aniline (C6H5NH2\mathrm{C_6H_5NH_2}C6​H5​NH2​), the lone pair on nitrogen is delocalized into the benzene ring by resonance, so it is less available for protonation.
    • In acetamide (CH3CONH2\mathrm{CH_3CONH_2}CH3​CONH2​), the lone pair on nitrogen is even more strongly delocalized toward the carbonyl group: CH3CONH2↔CH3C(=O−)=NH2+\mathrm{CH_3CONH_2 \leftrightarrow CH_3C(=O^-) = NH_2^+}CH3​CONH2​↔CH3​C(=O−)=NH2+​ Because of this resonance with the carbonyl group, the lone pair is much less available for accepting a proton.

    Therefore, acetamide is much less basic than aniline.

    So the statement "Aniline is less basic than acetamide" is false.

  2. Check Statement II: "In aniline, the lone pair of electrons on nitrogen atom is delocalized over benzene ring due to resonance and hence less available to a proton."

    This is correct. In aniline, the nitrogen lone pair participates in resonance with the aromatic ring: C6H5NH2↔resonance structures\mathrm{C_6H_5NH_2 \leftrightarrow resonance\ structures}C6​H5​NH2​↔resonance structures Hence the lone pair is less available for protonation compared with aliphatic amines.

    So Statement II is true.

  3. Conclusion:

    • Statement I: False
    • Statement II: True

    Therefore, the correct option is: B\boxed{\text{B}}B​

  4. Comparison with stored answer:

    Stored correct answer = B

    My derived answer = B

    Hence, they agree.

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