alcohols, ethers and epoxides

Question 1

What happens in an epoxide opening

Answer 1

epoxide opening occurs when epoxide reacts with nucleophile under acidic conditions where an OH group is added. Nuclophiles - OH, ethers, halides - nucloephile does not have to be strong because the epoxide has considerable ring strain and thus is already reactive

Question 2

what condidtions can an epoxide opening occur? How is the sterochemistry of the product controlled?

Answer 2

Can occur in both basic and acidic. Acidic nucleophilic substitution is added onto the more substituted carbon of the epoxide. Basic considitions the nucleophilic is added to least substitued carbon on the epoxide. - the BASE is BASIC so it will go through easiest/simpliest way - the ACID likes fun and rebellious -> will go through more substitued way

Question 3

How are epoxides formed? Give one example

Answer 3

Epoxides may be formed from alkenes and peracids which are HO-O-COR

Question 4

How should we use epoxides to increase carbon chain?

Answer 4

Using Girgnard reagents. Because the grignards are very strong BASES they will attack the less hindered position of the epoxide