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Compounds Containing Nitrogen question

2005 · Shift 0 · Q20
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Compounds Containing Nitrogen question

2005 · Shift 0 · Q20

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Amongst the following the most basic compound is
  1. A
    benzylamine
  2. B
    aniline
  3. C
    acetanilide
  4. D
    p-nitroaniline
View written solutionFree

Correct answer: A

  1. Concept of basicity in amines

    Basicity depends on the availability of the lone pair on nitrogen for donation to a proton.

    • Greater availability of the lone pair ⇒\Rightarrow⇒ stronger base.
    • If the lone pair is delocalized by resonance, basicity decreases.
    • Electron-withdrawing groups also decrease basicity.
  2. Examine each option

    (A) Benzylamine, C6H5CH2NH2\mathrm{C_6H_5CH_2NH_2}C6​H5​CH2​NH2​

    • The amino group is attached to a CH2\mathrm{CH_2}CH2​ group, not directly to the benzene ring.
    • Therefore, the lone pair on nitrogen is not conjugated with the aromatic ring.
    • It behaves like an aliphatic amine, so it is fairly basic.

    (B) Aniline, C6H5NH2\mathrm{C_6H_5NH_2}C6​H5​NH2​

    • Here, −NH2\mathrm{-NH_2}−NH2​ is directly attached to the benzene ring.
    • The lone pair on nitrogen is delocalized into the benzene ring by resonance.
    • Hence, the lone pair is less available for protonation.
    • So aniline is less basic than benzylamine.

    (C) Acetanilide, C6H5NHCOCH3\mathrm{C_6H_5NHCOCH_3}C6​H5​NHCOCH3​

    • This is an amide derivative.
    • The nitrogen lone pair is strongly delocalized toward the carbonyl group: −NHCOCH3↔−N+=C(O−)CH3\mathrm{-NHCOCH_3 \leftrightarrow -N^+=C(O^-)CH_3}−NHCOCH3​↔−N+=C(O−)CH3​
    • Due to this strong resonance, the lone pair is much less available.
    • Therefore, acetanilide is very weakly basic.

    (D) ppp-Nitroaniline

    • Like aniline, the nitrogen lone pair is delocalized into the benzene ring.
    • Additionally, the −NO2\mathrm{-NO_2}−NO2​ group is a strong electron-withdrawing group by both −I-I−I and −M-M−M effects.
    • This further decreases electron density on nitrogen.
    • Hence, ppp-nitroaniline is less basic than aniline.
  3. Order of basicity

    From the above analysis: benzylamine>aniline>p-nitroaniline\mathrm{benzylamine > aniline > p\text{-}nitroaniline}benzylamine>aniline>p-nitroaniline and acetanilide is the least/basicity is very low due to amide resonance.

    So the most basic compound is: benzylamine\boxed{\text{benzylamine}}benzylamine​

  4. Option check

    • A: benzylamine — correct
    • B: aniline — less basic due to resonance
    • C: acetanilide — very weak base due to amide resonance
    • D: ppp-nitroaniline — even less basic due to −NO2\mathrm{-NO_2}−NO2​ group

Therefore, the correct answer is A.

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