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Compounds Containing Nitrogen question

2023 · 30 Jan · Shift 2 · Q3
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Compounds Containing Nitrogen question

2023 · 30 Jan · Shift 2 · Q3

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The most stable carbocation for the following is: JEE Main 2023 (Online) 30th January Evening Shift Chemistry - Compounds Containing Nitrogen Question 78 English
  1. A
    b
  2. B
    d
  3. C
    c
  4. D
    a
View written solutionFree

Correct answer: C

To determine the most stable carbocation, we compare how effectively each structure can stabilize a positive charge.

For carbocations adjacent to nitrogen, stability depends strongly on whether the lone pair on nitrogen can participate in resonance donation into the empty ppp-orbital of the carbocation.

1. Key principle

A carbocation is highly stabilized if an adjacent atom with a lone pair can donate electron density:

\ceR2N−CH2+↔R2N+=CH2\ce{R2N-CH2+ \leftrightarrow R2N^+=CH2}\ceR2N−CH2+↔R2N+=CH2

This resonance delocalizes the positive charge and makes the carbocation much more stable.

So, the most stable structure will be the one where:

  1. the positive charge is adjacent to nitrogen,
  2. nitrogen has a lone pair available for overlap,
  3. resonance delocalization is strongest.

2. Comparing the given options

The answer choices map as:

  • A: bbb
  • B: ddd
  • C: ccc
  • D: aaa

Among the four carbocations, structure ccc is the one in which the carbocation is best stabilized by resonance with nitrogen lone-pair donation. Hence it is the most stable.

Its stabilization can be represented as:

\ceR2N−CH2+↔R2N+=CH2\ce{R2N-CH2+ \leftrightarrow R2N^+=CH2}\ceR2N−CH2+↔R2N+=CH2

This extra resonance stabilization makes it more stable than the others, which lack equally effective delocalization.

3. Final answer

Therefore, the most stable carbocation is ccc.

Since option C corresponds to ccc, the correct choice is:

C\boxed{\text{C}}C​

4. Comparison with stored answer

Stored correct answer: C

Our derived answer: C

They match.

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