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Organic Chemistry 2

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Moderate

Aldehyde Multistep Transformation VII

ORGO2-HKMYCG

What is the best reagent sequence for successfully accomplishing the following transformation?

Created for Albert.io. Copyright 2016. All rights reserved.

A
  1. Strong Base (e.g., LDA)
  2. $H_2C=CHCH_2Br$
  3. $H_2SO_4$, then $H_2O$ and heat
B
  1. $BH_3•THF$, then basic $H_2O_2$
  2. $PCC$
  3. $H_2C=CHCH_2MgCl$, then aqueous workup
C
  1. $BH_3•THF$, then basic $H_2O_2$
  2. PCC
  3. $H_2C=CHCH_2Br$
D
  1. mCPBA (m-chloroperoxybenzoic acid)
  2. $H_2C=CHCH_2MgCl$, then aqueous workup