How could the following transformation could be carried out.
C6H5C=CH --> C6H5CH2CH20H
I don't know how you would get a primary alcohol because I thought that following Markovnikov's rule any reaction would involve addition onto the other carbon.
To carry out the transformation of C6H5C=CH to C6H5CH2CH2OH, you would need to perform a two-step reaction called hydroboration-oxidation. This reaction bypasses Markovnikov's rule and leads to the formation of a primary alcohol.
Here is how you can proceed:
Step 1: Hydroboration
Hydroboration involves the addition of borane (BH3) to the carbon-carbon double bond. Borane is typically used in the form of borane-dimethyl sulfide complex (BH3•SMe2) for safer handling.
The hydroboration of C6H5C=CH proceeds as follows:
C6H5C=CH + BH3•SMe2 → C6H5CH2BH2SMe2
In this step, boron is added to the less substituted carbon of the double bond. This anti-Markovnikov addition is possible because the reaction proceeds through the concerted syn addition of boron and hydrogen across the double bond.
Step 2: Oxidation
After hydroboration, the boron is replaced with a hydroxyl group (-OH). This oxidation step is typically achieved using hydrogen peroxide (H2O2) and a basic solution, such as sodium hydroxide (NaOH).
The oxidation of C6H5CH2BH2SMe2 proceeds as follows:
C6H5CH2BH2SMe2 + H2O2 + NaOH → C6H5CH2OH + H2O + H2O + NaSMe2
In this step, the boron atom is replaced by a hydroxyl group, resulting in the formation of the desired primary alcohol, C6H5CH2OH.
So, by performing a hydroboration-oxidation reaction, you can successfully transform C6H5C=CH to C6H5CH2CH2OH, obtaining a primary alcohol.