Question

explain the hyperconjugation effect with an example.

Answer 1

When a H–C bond is attached to an unsaturated system such as double bond or a benzene ring, the sigma (σ) electrons of the H–C bond interact or enter into conjugation with the unsaturated system. 

The interactions between the electrons of systems (multiple bonds) and the adjacent bonds (single bonds) of the substituent groups in organic compounds is called hyperconjugation. 

The concept of hyperconjugation was developed by Baker and Nathan and is also known as Baker and Nathan effect.

For example in propene

refer to my image for understanding this effect in propene

Answer 2

Answer:

Hyperconjugation is an electronic effect that occurs when an electron-rich group, such as an alkyl or vinyl group, donates electrons to an adjacent empty or partially filled antibonding orbital, usually a σ* (sigma-star) orbital.

Explanation:

Hyperconjugation is an electronic effect that occurs when an electron-rich group, such as an alkyl or vinyl group, donates electrons to an adjacent empty or partially filled antibonding orbital, usually a σ* (sigma-star) orbital. This donation stabilizes the molecule, as the electrons in the antibonding orbital become partially filled, reducing the energy of the molecule.

One of the best examples of hyperconjugation is the stability of alkyl carbocations. Carbocations are highly reactive intermediates that are formed in many organic reactions. An alkyl carbocation is stabilized by hyperconjugation because the adjacent alkyl group can donate electrons to the empty p orbital of the carbocation.

For example, consider the formation of the tert-butyl carbocation (t-Bu+) from tert-butyl chloride (t-BuCl) in the presence of a strong Lewis acid, such as aluminum chloride (AlCl3):

CH3

|

H3C-C-Cl + AlCl3 → H3C-C+ -AlCl4

|

t-Bu

In this reaction, the t-butyl group (t-Bu) stabilizes the carbocation through hyperconjugation. The three adjacent C-H bonds of the t-butyl group donate electrons to the empty p orbital of the carbocation, as shown in the following diagram:

H3C-C-H H H

| | |

H H H

| | |

H3C-C+ -Cl → H3C-C+ -Cl

| | |

H H H

| | |

t-Bu t-Bu t-Bu

The resulting positive charge is delocalized over the t-butyl group, making the carbocation more stable than it would be without hyperconjugation. This stability allows the reaction to proceed more easily, which is why t-BuCl reacts readily with AlCl3 to form t-Bu+ -AlCl4- and HCl.

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