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Basics of Organic Chemistry question

2022 · 27 Jul · Shift 1 · Q9
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Basics of Organic Chemistry question

2022 · 27 Jul · Shift 1 · Q9

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Given below are two statements: one is labelled as Assertion A and, the other is labelled as Reason R. Assertion A: [6] Annulene, [8] Annulene and cis-[10] Annulene, are respectively aromatic, not-aromatic and aromatic. JEE Main 2022 (Online) 27th July Morning Shift Chemistry - Basics of Organic Chemistry Question 121 English Reason R: Planarity is one of the requirements of aromatic systems. In the light of the above statements, choose the most appropriate answer from the options given below.
  1. A
    Both A and R are correct and R is the correct explanation of A.
  2. B
    Both A and R are correct but R is NOT the correct explanation of A.
  3. C
    A is correct but R is not correct.
  4. D
    A is not correct but R is correct.
View written solutionFree

Correct answer: D

  1. Recall the conditions for aromaticity

    A cyclic compound is aromatic if it satisfies all of the following:

    1. It is cyclic.
    2. It is fully conjugated.
    3. It is planar.
    4. It has (4n+2)π(4n+2)\pi(4n+2)π electrons (Hückel rule).

    If planarity/full conjugation is lost, the compound is non-aromatic. If it is planar and conjugated but has 4nπ4n\pi4nπ electrons, it is antiaromatic.

  2. Examine the compounds in the Assertion

    (i) [6][6][6] Annulene

    [6][6][6] Annulene is benzene. It is planar, fully conjugated, and has 6π6\pi6π electrons. Since 6=4n+26 = 4n+26=4n+2 for n=1n=1n=1, it is aromatic.

    So the first part is correct.

    (ii) [8][8][8] Annulene

    [8][8][8] Annulene has 8π8\pi8π electrons. If it were planar, it would be antiaromatic (4n, n=2)(4n,\ n=2)(4n, n=2). To avoid this, it adopts a non-planar tub-shaped structure, so continuous overlap is lost. Therefore, it is not aromatic (non-aromatic).

    So the second part is correct.

    (iii) cis-[10][10][10] Annulene

    A [10][10][10] annulene has 10π10\pi10π electrons, which satisfies Hückel rule: 10=4n+2(n=2)10 = 4n+2 \quad (n=2)10=4n+2(n=2) However, cis-[10][10][10] annulene is not planar because of steric repulsion between inner hydrogens, so it cannot achieve the required continuous planar conjugation. Hence, cis-[10][10][10] annulene is not aromatic.

    Therefore, the statement saying that cis-[10][10][10] annulene is aromatic is incorrect.

    So the overall Assertion A is false.

  3. Examine the Reason

    Reason R states: Planarity is one of the requirements of aromatic systems.

    This is a standard condition for aromaticity, so R is correct.

  4. Choose the correct option

    • Assertion A: Not correct
    • Reason R: Correct

    Therefore, the correct option is:

    D: A is not correct but R is correct.

  5. Comparison with stored answer

    Stored correct answer: D

    My derived answer: D

    They agree.

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