Question: Draw a stepwise mechanism for the following reaction. This reaction combines two processes together: the opening of an epoxide ring with a nucleophile and the addition of an electrophile to a carbon–carbon double bond. (Hint: Begin the mechanism by protonating the epoxide ring.)
Ring-opening of an epoxide is completed by nucleophiles or Lewis bases in acidic and basic mediums.
In the basic medium, the epoxide gives a more substituted alcohol, and in the acidic medium, it gives a less substituted alcohol.
The addition of an electrophile gives the electron-vacant position where a nucleophile attacks and forms the desired product.
The mechanism of intramolecular ring-opening in the acidic medium gives a less substituted alcohol. Ring-opening is completed by the alkene nucleophile.
The attack of alkene generates a carbocation that is attacked by the water molecule.
The mechanism is shown below:
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