Chapter 4 Number 43

 

For the first part we react the alkene with water and Sulfuric acid. We add an alcohol to the second carbon of the double bond. 1,2-hydride shift is performed to get a tertiary alcohol which is more stable than the secondary. For the second part we go through oxymercuration-reduction so we all the alcohol to the second carbon of the double bond. There is no hydride shift because there is no carbocation rearrangement. The third part is hydroboration-oxidation. For that we add the alcohol to the least stable carbon, that's why its added to the first carbon, which is primary, instead of the second carbon.