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Chapter 8: Q13P (page 334)

Which carbocation in each pair is more stable?

b. CH3OC+H2 or CH3NHC+H2

Short Answer

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a)

Step by step solution

01

Resonating structures             

a)

02

Final answer

a) The compound with delocalized electrons is more stable.

b) Nitrogen is less electronegative than oxygen then it is better able to share positive charge.

c) In order for electron delocalisation to occur, the atoms that share the pi electrons must be the same plane so their p orbitals can overlap. The two bulky tert-butyl groups do not allow enough room for the group with the positively charge carbon to be in the same plane as the benzene ring. Therefore the carbocation can't be stabilized by electron delocalization because the p orbital of the positively charge carbon can't overlap the p orbital of the benzene ring since they are not in the same plane.

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