Advanced Organic Chemistry Practice Problems 2021 (Working)

"Propose a mechanism for the following reaction:

The days turned into weeks, and Alex found herself looking forward to each new practice problem. She started to see the beauty in the complex reactions and the clever strategies that Dr. Thompson had designed to help them learn.

[PhCH2CH2Br + (CH3)3SiCl → PhCH=CH2 + (CH3)3SiBr + HCl]

Just as Alex was about to give up, she remembered a crucial concept from her previous lecture: the use of silicon-based reagents in organic synthesis. A lightbulb went off in her head, and she quickly jotted down a possible mechanism.

"Predict the product of the following reaction: