exam3sp03chem12b

exam3sp03chem12b - Chem 12B Dr. Harrison EXAM #3 Name _ Sp...

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Chem 12B EXAM #3 Name __________________ Dr. Harrison Sp 03 1. (21 pts) Demonstrate your command of organic chemistry by filling in the necessary reagents or products for the synthesis below. Take special care to write all steroeisomers possible for each product. a. b. c. NH 2 X X N N OH d. e. Et-O O-Et O O 1) NaOEt 2) Br Br 3) NaOEt H 3 O + X f. CH 2 CO 2 Et CH 2 CO 2 Et H H 1. NaOEt 2. H 3 O + X H 2 N OH O Br CH COOEt COOEt H O X X OH O H HO 1) Br 2 / PBr 3 2) H 2 O NH 3 excess X H 3 O + H 3 N + H C C CH 2 Ph OCH 2 CH 3 O H 2 , Pd X X
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g. H 3 C O O CHO 1. LDA 2. X h. SH + O O NaOCH 3 X i. Br X OH O OH O Br CH 2 N 2 X X 1)NaN 3 2) H 2 /Pd X j. X 1. MCPBA 2. Heat NH 2 k. l. X NH 2 O CH 3 Br 2 , NaOH H 2 O m. X X O O OEt O O CO 2 ET 2.(6 pts) How can the amino acids be separated by enzymic resolution? Be specific. H CHO OH OH H H HO OH H CH 2 OH CHO OH H H HO OH H CH 2 OH H OH OH H H HO OH H CH 2 OH X X CHO H OH + epimer
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3. (8 pts) Explain which compound is more acidic and circle the most acidic proton.
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exam3sp03chem12b - Chem 12B Dr. Harrison EXAM #3 Name _ Sp...

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