Question

Tert butyl benzene does not show hyperconjugation

Answer 1

Hyperconjugation is not seen in Tert butyl benzene is given below

Explanation:

• Tert-butyl benzene does not have any alpha hydrogen, while toulene has a alpha hydrogen, so in toulene alpha hydrogen increases the electron density by hyperconjugation and also by inductive effect and in tert-butyl benzene electron density is increased only by inductive effect, as we know hyperconjugation is dominant over inductive so toulene is more reactive towards electrophilic aromatic substitution.

• The hyperconjugation effect on molecular structural stability is studied by performing first-principles calculations on the tert-butyl and its derived C4Hn(n = 4–10) isomer structures. Four of the isomer structures with n = 7–10 were found to show hyperconjugation similar to that in the tert-butyl, with hyperconjugation orbital energies decreasing with the increase of the number of hydrogen atoms participating in the hyperconjugation (PIH). The distribution of charge carried by the PIH hydrogen atoms is uniform, which reveals a delocalization character in the electronic structures; and the PIH hydrogen atoms are found responsible for the main IR spectrum peak relating to C-H stretching vibration.

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