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Under certain conditions, HBr adds to 2-methylpropene to give predominantly 2-bromo-2-methylpropane — Organic Chemistry Chemistry Question

Question

Under certain conditions, HBr adds to 2-methylpropene to give predominantly 2-bromo-2-methylpropane rather than isomeric 1-bromo-2-methylpropane. Which is the best mechanistic explanation for this regioselectivity?

A.

H+ adds preferentially to C-1 to form the more stable carbocation.

✓ Correct
B.

Br– adds preferentially to C-2 to form the more stable carbanion.

C.

H• adds preferentially to C-1 to form the more stable radical.

D.

Br• adds preferentially to C-2 to form the more stable radical.

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