1.

Explain why (CH_(3))_(3)overset(+)(C) is more stable than CH_(3)overset(+)(C)H_(2) and overset(+)(C)H_(3) is the least stable cation.

Answer»

Solution :`(CH_(3))_(3)overset(+)(C)` has nine `alpha`-hydrogens and hence has nine hyperconjugation structures while `CH_(3)overset(+)(C)H_(2)` has only THREE `alpha`-hydrogens and hence has only three hyperconjugation structures. As a RESULT, `(CH_(3))_(3)C^(+)` is more stable than `CH_(3)CH_(2)^(+)`. In contrast in `CH_(3)^(+)`, the vacant p-orbital is PERPENDICULAR to the plane in which the three C-H bonds lie and hence cannot overlap with it. THUS, `CH_(3)^(+)` is not stabilized by hyperconjugation and hence is the least stable of the three cations.


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