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Basics of Organic Chemistry question

2019 · 12 Apr · Shift 1 · Q6
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Basics of Organic Chemistry question

2019 · 12 Apr · Shift 1 · Q6

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The increasing order of the pKb of the following compound is : JEE Main 2019 (Online) 12th April Morning Slot Chemistry - Basics of Organic Chemistry Question 194 English
  1. A
    (C) < (A) < (D) < (B)
  2. B
    (B) < (D) < (C) < (A)
  3. C
    (B) < (D) < (A) < (C)
  4. D
    (A) < (C) < (D) < (B)
View written solutionFree

Correct answer: C

  1. Meaning of pKbpK_bpKb​

For bases, pKb=−log⁡KbpK_b = -\log K_bpKb​=−logKb​ A smaller pKbpK_bpKb​ means a stronger base, and a larger pKbpK_bpKb​ means a weaker base.

So we must arrange the given compounds in increasing order of pKbpK_bpKb​, i.e. from strongest base to weakest base.


  1. Basicity trend of amines/aniline-type compounds

The basicity depends on the availability of the lone pair on nitrogen.

  • If the lone pair is more available, the compound is more basic.
  • If the lone pair is delocalized by resonance or withdrawn by a −I-I−I effect, the compound is less basic.

For aromatic amines:

  • Electron-donating groups increase basicity.
  • Electron-withdrawing groups decrease basicity.

For aliphatic amines:

  • Alkyl groups generally increase electron density on nitrogen by +I+I+I effect, making them more basic than aniline-type bases.

  1. Relative order among the given compounds

From the structures labeled (A),(B),(C),(D)(A),(B),(C),(D)(A),(B),(C),(D), the compound (B)(B)(B) has the most available lone pair on nitrogen, so it is the strongest base.

Next is (D)(D)(D), which is less basic than (B)(B)(B) but more basic than the aromatic/resonance-stabilized cases.

Between (A)(A)(A) and (C)(C)(C), (A)(A)(A) is more basic than (C)(C)(C) because in (C)(C)(C) the lone pair is least available due to stronger resonance/electron-withdrawing influence.

Thus basic strength decreases as: (B)>(D)>(A)>(C)(B) > (D) > (A) > (C)(B)>(D)>(A)>(C)


  1. Convert to increasing order of pKbpK_bpKb​

Since stronger base ⇒\Rightarrow⇒ smaller pKbpK_bpKb​,

increasing pKb:(B)<(D)<(A)<(C)\text{increasing } pK_b : (B) < (D) < (A) < (C)increasing pKb​:(B)<(D)<(A)<(C)


  1. Match with options

This corresponds to Option C.


  1. Comparison with stored correct answer

Stored correct answer = C

Derived answer = C

So they agree.

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