W03 problems5c key

W03 problems5c key - O Ph 3 P HCl HCl Ph 3 P Cl Ph 3 P H O...

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H O O Br O O O OH OH HIO 4 OTs Cu Li OH PPh 3 Br OH OH Br O O OH 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 . Diphenyl-methanone 5,5-Dimethyl-cyclohexane-1,3-dione 5( R )-Hydroxy-hexan-2-one 1-Bromo-5-methyl-hex-3-en-2-one 5(S)-Isopropenyl-2-methyl -cyclohex-2-enone 2( S ),5-Dimethyl-hex-4-enal 1) Li, ether; then CuI No reaction, periodic acid is specific for cis-diols. Problem Set-5/Chapter 16 Aldehydes/Ketones (page 1) Chem 30B-Winter 2003 TA: Chris Mortko, [email protected] 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) P r o v i d e t h e r e a g e n t s o r p r e d i c t p r o d u c t ( s ) n e c e s s a r y t o c o m p l e t e t h e f o l l o w i n g s y n t h e s e s . a) b) c) d) 1) PCC 2) 3) H 2 , Pt e) 1) O 3 2) DMS 3) MeLi; then H + 2)
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A CuLi O Ph Cl O O A = Br H O H 2 N HO OH (i-Pr) 2 NH B = B HCl O Ph
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Unformatted text preview: O Ph 3 P HCl HCl Ph 3 P Cl Ph 3 P H O O Cl-N N O O PPh 3 PPh 3 O OH PPh 3 O Show how each of the following alkenes can be synthesized by a Wittig reaction. Include the complete reaction mechanism and disconnections. a) b) F i l l i n t h e b o x e 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 . + I d e n t i f y c o m p u n d s A a n d B . 1) 1) CH 3 Li 2) H + , H 2 O Retrosynthesis +-+-target + Retrosynthesis + Same Mechanism as above Problem Set-5/Chapter 16 Aldehydes/Ketones (page 2)...
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This note was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Winter '05 term at UCLA.

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W03 problems5c key - O Ph 3 P HCl HCl Ph 3 P Cl Ph 3 P H O...

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