CHEM 140A Lecture Notes - Lecture 18: Epoxide, Alkoxide, Leaving Group

• School: UCSD
• Department: Chemistry and Biochemistry
• Course: CHEM 140A
• Professor: Joseph M Oconnor

Document Summary

Ch3ch2-o-ch2ch3 ---h-x ch3-ch2-oh + ch3ch2-cl: first an oxygen attaches to an h+ and becomes o, then the x- comes in and cuts off one half of the ether and attaches. Epoxides have a ton of strain (ring, eclipsing, angle, etc. : when the ring opens up, a lot of the strain is relieved. Epoxide + nu- alkoxide (strong base, so weak leaving group: the result of an epoxide reacting with a nucleophile will result in a weak leaving group. The o- on the epoxide reacts with an h+ to become oh attached, so. Nucleophiles prefer to attack the lower degree carbon (primary, secondary, tertiary)