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0 0 Select the two-step synthesis that will convert the starting material to the target alcohol pictured OH 2. 1. Br 1. tBuoK
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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.

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