W03 problems3c key

W03 problems3c key - D r a w t h e s t r u c t u r e f o r...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Problem Set-3 Retrosynthetic Analysis/Ethers Chapters 10 and 11, Page 1 Chem 30B-Winter 2003 TA: Chris Mortko, cmortko@chem.ucla.edu D i s c u s s i o n S e c t i o n s Wednesdays: 8-9am (MS 3915H), 9-10am (Boelter 5273) O f f i c e H o u r Wednesday 10-11am (Young 1379) Show the retrosynthetic analysis that would be used to synthesize the following targets . H O Using ethyne as the starting material, how can the following compounds be prepared? O H O H H starting material H H I Br EtO H H H H H H a b c d e a. b. c. d. e. SM 1. (sia) 2 BH 2. H 2 O 2 , NaOH SM 1.NaNH 2 2. EtBr H 1. LDA 2. CH 3 Br H 2 , Pd CaCO 3 SM 1.NaNH 2 2. EtBr H 1. LDA 2. CH 3 Br 2 H 2 , Pd H O SM 1.NaNH 2 2. MeBr H HgSO 4 H 2 SO 4 OH O SM 1.NaNH 2 2. EtBr H 1. LDA 2. CH 3 Br Br 2 CCl 4 Br Br I CH 3 I + + + Br Br
Background image of page 1

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

View Full DocumentRight Arrow Icon
Diethyl ether tert- Butyl methyl ether dicyclohexyl ether methyl vinyl ether
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: D r a w t h e s t r u c t u r e f o r e a c h o f t h e f o l l o w i n g c o m p o u n d s . (Ethoxyethane) (2-Methoxy-2-methylpropane) (Methoxyethene) (Cyclohexoxycyclohexane) W r i t e t h e p r o d u c t s f o r t h e f o l l o w i n g r e a c t i o n s u s e d t o s y n t h e s i z e e t h e r s O- Na + + CH 3 Br O-K + + CH 3 Br Br + CH 3 O-Na + 1. (sia) 2 BH 2. H 2 O 2 , NaOH OH H O H O CH 3 O CH 3 1.BH 3 THF 2. H 2 O 2 , NaOH H BH 3 THF B B BH 3 THF W r i t e t h e p r o d u c t s f o r t h e f o l l o w i n g r e a c t i o n s . O O CH 3 O O OH OH O O B...
View Full Document

Page1 / 2

W03 problems3c key - D r a w t h e s t r u c t u r e f o r...

This preview shows document pages 1 - 2. Sign up to view the full document.

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