Organic Chemistry

SOLUTION E15.1b

The left reaction (isopropyl, 1) would be faster as it has the lowest activation barrier leading to its intermediate. The carbocation is stabilized due to the electron donating abilities of the isopropyl group (hyperconjugation). The right reaction (bromo, 2) would be slower as it has the higher activation barrier and less stabilized (higher energy) carbocation intermediate.

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