W03 problems9c

W03 problems9c - 2 HCl H 2 O Claisen Condensation-Base catalyzed synthesis of of-ketoesters from esters with 2-hydrogens 2 HCl H 2 O 1 MeO-Na D r a

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MeO OMe O O EtO Br Br O O OEt O O CO 2 Et Br Br Problem Set-9/Chapter 19 Enolate Anions and Enamines_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) C o m p l e t e t h e f o l l o w i n g r e a c t i o n s e q u e n c e s b e l o w . 1. EtO - Na + 1. EtO - Na + 2. 3. NaOH, H 2 O 4. HCl, H 2 O 5. heat 2. 3. HCl, H 2 O 4. heat 2. Malonic Ester Synthesis---Preparation of mono and disubstituted acetic acids. 1. MeO - Na + 2. 3. NaOH, H 2 O 4. HCl, H 2 O 5. heat 6. MeO - Na + 7. 8. NaOH, H 2 O 9. HCl, H 2 O 10. heat Acetoacetic Ester Synthesis---Preparation of mono and disubstituted acetones. O O O S y n t h e s i z e 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 b y u s i n g t h e a c e t o a c e t i c e s t e r s y n t h e s i s . 1. MeO - Na +
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O MeO O OEt O O Ph OMe O EtO OEt O O MeO O OMe O N H O Cl O O Br MeO OMe O O MeO OMe O O H OMe O Problem Set-9/Chapter 19 Enolate Anions and Enamines_Page 2 1. MeO - Na +
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Unformatted text preview: 2. HCl, H 2 O Claisen Condensation---Base catalyzed synthesis of of -ketoesters from esters with 2-hydrogens 2. HCl, H 2 O 1. MeO-Na + D r a w t h e s t r u c t u r e s o f t h e-k e t o e s t e r s f o r m e d b y t h e C l a i s e n c o n d e n s a t i o n o f m e t h y l p r o p a n o a t e w i t h e a c h e s t e r . Dieckmann Condensation---Intramolecular Claisen Condensation of a diester to give 5-6 membered rings Enamines HCl/H 2 O 2. HCl/H 2 O 1. HCl/H 2 O Michael Reaction Robinson Annulation 1. NaOEt/EtOH 2. 2. NaOEt/EtOH 1. NaOEt/EtOH 2. HCl/H 2 O HCl...
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This homework help 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 problems9c - 2 HCl H 2 O Claisen Condensation-Base catalyzed synthesis of of-ketoesters from esters with 2-hydrogens 2 HCl H 2 O 1 MeO-Na D r a

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