Week_3.4_PurpleBook_Answers

Week_3.4_PurpleBook_Answers - 80 Ether Syntheses 1 Week 3...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
O O O Ether Syntheses 1 example: O O: example: 1. Devise efficient syntheses for each of the following types of ether. Primary—Primary O: example: Choose either SN2 route (typical Williamson synthesis): Br Primary—Secondary O: example: Secondary—Secondary : tough! Either way gives a strong probability of elimination! Show S N 2andS N 1 Br Use the secondary alkoxide as the nucleophile, and a primary halide in an S N 2 process: Tertiary—anything OH Use a tertiary alcohol or an alkene, a trace of acid, and lots of the other alcohol, in an S N 1-type route: + HO + + HO likely to give E2 with acid, likely to give some E1 OH + + HO + with acid, use large excess of the primary alcohol + HO with acid, use large excess of the alcohol. (Can you show mechanism?) with acid, use large excess of the alcohol. (Can you show mechanism?) CH 3 I Week 3 80
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Ether Syntheses 2 1. a) The following ethers can be synthesized by an S N 2 reaction from two different combinations of an alkoxide and an alkyl halide. For each molecule, show the combinations of alkyl halide and alkoxide that could comb inetoformbond 1 and the combination that could combine to form bond 2 and circle the pair that will react to provide a higher yield of the ether. O Me Me O Me Me Me 1 2 1 2 1 2 1 2 S N 2 Starting Materials: S N 2 Starting Materials: S N 2 Starting Materials: S N 2 Starting Materials: O Me 1 2 1 2 S N 1 Starting Materials: S N 1 Starting Materials: Me O Me Me Me 1 2 1 2 S N 1 Starting Materials: S N 1 Starting Materials: b) Consider using an S N 1
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

Page1 / 10

Week_3.4_PurpleBook_Answers - 80 Ether Syntheses 1 Week 3...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online