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Basics of Organic Chemistry question

2021 · 27 Jul · Shift 2 · Q4
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Basics of Organic Chemistry question

2021 · 27 Jul · Shift 2 · Q4

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Given below are two statements : Statement I : Hyperconjugation is a permanent effect. Statement II : Hyperconjugation in ethyl cation (CH3−C+H2)\left( {C{H_3} - \mathop C\limits^ + {H_2}} \right)(CH3​−C+​H2​) involves the overlapping of Csp2−H1s{C_{s{p^2}}} - {H_{1s}}Csp2​−H1s​ bond with empty 2p orbital of other carbon. Choose the correct option :
  1. A
    Both statement I and statement II are false
  2. B
    Statement I is incorrect but statement II is true
  3. C
    Statement I is correct but statement II is false
  4. D
    Both statement I and statement II are true.
View written solutionFree

Correct answer: C

  1. Analyze Statement I: Hyperconjugation is a permanent effect.

    Hyperconjugation is the delocalization of electrons of a σ\sigmaσ-bond (usually α\alphaα-C–H or C–C bond) into an adjacent empty ppp-orbital, partially filled ppp-orbital, or π\piπ-orbital.

    Since this electron delocalization exists in the ground state of the molecule whenever the required orbital arrangement is present, hyperconjugation is classified as a permanent effect (like inductive effect), not a temporary effect like electromeric effect.

    Therefore, Statement I is true.

  2. Analyze Statement II: Hyperconjugation in ethyl cation (CH3−C+H2)\left( CH_3-\overset{+}{C}H_2 \right)(CH3​−C+H2​) involves the overlapping of Csp2−H1sC_{sp^2}-H_{1s}Csp2​−H1s​ bond with empty 2p2p2p orbital of other carbon.

    In the ethyl cation:

    • The positively charged carbon is sp2sp^2sp2 hybridized and has an empty unhybridized 2p2p2p orbital.
    • Hyperconjugation occurs from the adjacent σ(C−H)\sigma(C-H)σ(C−H) bond of the methyl carbon into this empty 2p2p2p orbital.

    The donating bond is a σ\sigmaσ bond formed by overlap of:

    • carbon orbital on the methyl carbon, which is sp3sp^3sp3 hybridized,
    • hydrogen 1s1s1s orbital.

    So the bond involved is Csp3−H1sC_{sp^3}-H_{1s}Csp3​−H1s​, not Csp2−H1sC_{sp^2}-H_{1s}Csp2​−H1s​.

    Hence, Statement II is false.

  3. Conclusion:

    • Statement I: True
    • Statement II: False

    Therefore, the correct option is: C\boxed{\text{C}}C​

  4. Comparison with stored answer:

    Stored correct answer = C

    My derived answer = C

    So, they agree.

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