Question

0 0 Select the two-step synthesis that will convert the starting material to the target alcohol pictured OH 2. 1. Br 1. tBuoK/BUOH b) a) 1. EtoNa/EtOH 2. a) BH/THF b) H2O2 OH 2. a) Hg(OAC) THF/H2O b) BHOH d) 1. tBuOK/BUOH c) 1. EtoNa/EtOH 2. a) Hg(OAC)2 THF/H20 b) BH, OH 2. a) BH3/THF b) H2O2 OH MacBook Air

Answer 1

Because hydrogen is abstracted from the less substituted position to give the alkene, bulky base will work.

If the base used would be EtONa/EtOH, it can abstract base from more substituted carbon due to absence of steric hindrance and can give a more substituted alkene which is not required.

t-BuOK/t-BuOH gives the less substituted alkene via E2 elimination.

In the next step, hydroboration-oxidation of alkene gives the required product because this undergoes markonikov addition to give an anti-markonikov product.

Oxymercuration-demercuration of alkene gives a markonikov product with OH attached to the more substituted carbon. This is not required, so options with this reagent are ruled out.

So, the correct option is option b.