Question

describe the steps an alkene in "cholesterol" is hydrated using a strong acid and water forming tertiary alcohol product

Answer 1

Step1: Alkene functional group is electron rich.

Step 2: While adding strong acid, the acid delivers proton. proton is electron deficient

Step 3: Therfore electron flow takes place from electron rich alkene of cholesterol to electron deficient proton.

Step 4: by accepting proton, alkene of cholestrol generates two possible carbocation intermediates i.e., tertiary carbocation and secondary carbocation.

step 5: Among tertiary carbocation and secondary carbocation, tertiary is more stable and it leads to major product by reacting with water .

Step 6: water acts as a nucleophil due to the availability of pair of electrons on oxygen and it will attack tertiary carbocation to give tertiary alcohol as a major product.

Note: Formation of ssecondary alcohol is also possible but it will be a minor product.