This preview shows page 1. Sign up to view the full content.
Unformatted text preview: reaction of the epoxide shown below? O ? 2. H 3 O + Product 1. CH 3 MgBr O H + O O O a) b) c) d) H 3 C MgBr H 3 C MgBr H 3 C MgBr H 3 C MgBr Comments: This is an example of nucleophilic ring opening of epoxides. It was sufficient to recognize that this is an S N 2 reaction, with the release of ring strain, providing the driving force. S N 2 reactions take place on the back-side of the leaving group ( σ * C-O bond is the LUMO) and on the less sterically crowded carbon. Grignards as strong bases cannot coexist with acids (excluding (a) as an option). Similar example was in TS4: 74....
View Full Document
This note was uploaded on 01/12/2010 for the course PSYCH 100 taught by Professor Matchock,robert during the Fall '07 term at Penn State.
- Fall '07