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Hyperconjugation is more pronounced in...

Hyperconjugation is more pronounced in

A

2 - methylpropene

B

but -2-ene

C

2,3 -dimethylbut - 2- ene

D

2- methylbut -2-ene

Text Solution

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The correct Answer is:
To determine where hyperconjugation is more pronounced, we need to analyze the number of alpha-hydrogens in the given options. Hyperconjugation is a stabilizing interaction that results from the overlap of a σ-bond orbital with an adjacent empty or partially filled p-orbital or π-orbital. The more alpha-hydrogens present, the greater the hyperconjugation effect. ### Step-by-Step Solution: 1. **Understanding Hyperconjugation**: - Hyperconjugation occurs when there are adjacent carbon atoms with hydrogen atoms (alpha-hydrogens) that can interact with a double bond or a positively charged carbon atom. - The more alpha-hydrogens present, the stronger the hyperconjugation effect. 2. **Analyzing Each Option**: - **Option A: 2-Methylpropene (C4H8)**: - Structure: CH3-CH=C(CH3)-CH3 - Alpha-hydrogens: - The double bond is between the second and third carbon. - The first carbon has 3 alpha-hydrogens, the second carbon has 1, and the third carbon has 3. - Total alpha-hydrogens = 3 + 1 + 3 = 7. - **Option B: Butyrene (C4H8)**: - Structure: CH3-CH=CH-CH3 - Alpha-hydrogens: - The double bond is between the second and third carbon. - The first carbon has 3 alpha-hydrogens, the second carbon has 1, the third carbon has 2, and the fourth carbon has 3. - Total alpha-hydrogens = 3 + 1 + 2 + 3 = 9. - **Option C: 2,3-Dimethylbutene (C6H12)**: - Structure: CH3-CH=C(CH3)-C(CH3)-CH3 - Alpha-hydrogens: - The double bond is between the second and third carbon. - The second carbon has 1 alpha-hydrogen, the third carbon has 1 alpha-hydrogen, and each of the two methyl groups contributes 3 alpha-hydrogens. - Total alpha-hydrogens = 1 + 1 + 3 + 3 + 3 = 11. - **Option D: 2-Methyl-1-butene (C5H10)**: - Structure: CH2=C(CH3)-CH2-CH3 - Alpha-hydrogens: - The double bond is between the first and second carbon. - The first carbon has 2 alpha-hydrogens, the second carbon has 3, and the third carbon has 2. - Total alpha-hydrogens = 2 + 3 + 2 = 7. 3. **Comparison of Alpha-Hydrogens**: - Option A: 7 alpha-hydrogens - Option B: 9 alpha-hydrogens - Option C: 11 alpha-hydrogens - Option D: 7 alpha-hydrogens 4. **Conclusion**: - The option with the maximum number of alpha-hydrogens is **Option C: 2,3-Dimethylbutene**, which has 11 alpha-hydrogens. Therefore, hyperconjugation is most pronounced in this compound. ### Final Answer: **Option C: 2,3-Dimethylbutene** has the most pronounced hyperconjugation due to having the maximum number of alpha-hydrogens.
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Knowledge Check

  • Hyperconjugation involves

    A
    Delocalization of `sigma`-electrons into an adjacent `pi`-bond
    B
    Delocalization of n-electrons into an adjacent double bond
    C
    Delocalization of `pi`-electrons into an adjacent `pi`-bond
    D
    All are true.
  • Hyperconjugation observed in

    A
    B
    `overset(.)CPh_(3)`
    C
    D
  • Hyperconjugation is not possible in

    A
    `CH_(3)-CH=CH_(2)`
    B
    `CH_(2)=CH_(2)`
    C
    D
    `CH_(3)-underset(CH_(3))underset(|)(C)=underset(CH_(3))underset(|)(C)-CH_(3)`
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    Hyperconjugation is defined as No bond resonance. The concept of hyperconjugation arose from the discovery of electron releasing pattern for alkyl groups. It involves sigma electrons of C-H bond. Greater the number of C-H bond ( alpha -hydrogen atom w.r.t. double bond) more will be hyperconjugative structures, more will be stability Heat of hydrogenation of alkene are affected by hyperconjugative effects. Which of the following is incorrect hyperconjugative structure?