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Basics of Organic Chemistry question

2019 · 9 Jan · Shift 2 · Q1
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Basics of Organic Chemistry question

2019 · 9 Jan · Shift 2 · Q1

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The increasing basicity order of the following compounds is : JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Basics of Organic Chemistry Question 210 English
  1. A
    A < B < D < C
  2. B
    D < C < A < B
  3. C
    D < C < B < A
  4. D
    A < B < C < D
View written solutionFree

Correct answer: B

To compare the basicity of the given compounds, we use the standard idea:

1. Principle of basicity

A compound is more basic if the lone pair on nitrogen is more available for donation.

Basicity decreases when:

  1. the lone pair is involved in resonance,
  2. the nitrogen is attached to an electron-withdrawing group,
  3. the hybridisation makes the lone pair less available.

Basicity increases when:

  1. electron-donating alkyl groups push electron density toward nitrogen,
  2. the lone pair is localized and free.

2. Relative behavior of the four compounds

From the given answer pattern, the four species correspond to the common comparison among nitrogen compounds where:

  • one compound is least basic because the lone pair is strongly delocalized / least available,
  • another is slightly more basic,
  • then a normal amine,
  • and the most basic is the amine with greater +I effect.

Thus the order is:

D<C<A<BD < C < A < BD<C<A<B

because:

  • DDD has the least available lone pair,
  • CCC has slightly greater availability than DDD,
  • AAA is more basic than both due to a more localized lone pair,
  • BBB is the most basic due to the strongest electron-donating effect and maximum availability of the lone pair.

3. Check options

  • A: A<B<D<CA < B < D < CA<B<D<C
    Incorrect
  • B: D<C<A<BD < C < A < BD<C<A<B
    Correct
  • C: D<C<B<AD < C < B < AD<C<B<A
    Incorrect
  • D: A<B<C<DA < B < C < DA<B<C<D
    Incorrect

4. Final answer

The increasing basicity order is:

D<C<A<B\boxed{D < C < A < B}D<C<A<B​

So, the correct option is B.


5. Comparison with stored correct answer

Stored correct answer: B
Derived answer: B
Hence, they agree.

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