322bf03_e3_key

322bf03_e3_key - Fall 2003 Organic Chemistry 322bL November...

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Unformatted text preview: Fall 2003 Organic Chemistry 322bL November 3, 2003 Exam 3 Name szgc‘ “E/ Initial of Last Name :1 T.A.‘s Name 1-________________ (30 pts) 2-________________ (15 pts) 3-_____________ (15 pts) 4-________________— (12 pts) 5-_—____________ (10 pts) 6 (8 pts) 7-__________—___ (10 pts) Total (100 pts.) lmdx . 1. Write the products of the following reactions. MSW-up. Show stereochemistry (only) if appropriate. (30 pts.) - \ Li a. + toluene \ '-\ I I N/ 110°C (/L [N/ ‘1 9% Ha - M ~ ' — ' d_ @MCHZCHZEH yL’N-Cllt at, 69:! CH3 ' (3 £3 2 0 Off e ‘ 1) Ag 0 t . e. CH3-CH2-CH2-CH2-fH-N(CH3)3 H220 CH3 Bra 2) A M130” © 1) n-Bu-Li (CH3)2$'CH3 ————-—-—> 2, O=o k. NaOEt '- EtO-C-CHZ-C-OEt + H2N-C-NH2 SI<- 2- GiVe" and acrylomtri'e» /\CN, and any other reagents you need, _ C‘————N . prepare &r\/ . Then outline a synthetic route to convert this T N 8—ketonitrile to decahydroquinoline. CE) (15 pts.) / [ya/x C 5WW/“Mfiflfiéfit‘. 3. Given aniline, acetyl chloride, acetic anhydride and any other reagents you need, prepare the sulfa drug below. (15 pts.) leqlv _ 4. Specify the reagents and conditions for each of the following transformations. (12 pts.) 5. Given diethyl malonate (EtOZC-CHZ-COZEt),and a suitable brominated alkane, efficarjy prepare 0—002” (10pm) CW((07/fl:\)1 i: crib/Cm— flg 'fléasz/EAL E1 \COfl‘ r i? 6- /C-C__>_H2-C-0Et CH3 Draw resonance structures for the anion produced by the treatment of this compound with a stoichiometric amount of sodium ethoxide. What is the product of this anion with bromobenzene? (8 pts.) 6 06 o C3 1 ‘ Qoécw AskoQHJK/ioa" gamma: 7. Given ethyl phenylacetate (Ph-CHa-C-OEt) and diethyl carbonate, outline a synthesis 002Et ‘ of diethyl phenylmalonate Qc< » 002Et 5 z 3 The key reaction used is an example of a cross Cb‘ifl] condensation. (10 pts.) ...
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322bf03_e3_key - Fall 2003 Organic Chemistry 322bL November...

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