first midterm 2004

first midterm 2004 - e " Page 3 of 5 g) 1....

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Page 1 of 5 Chemistry 118C Name____________________________________ F i r s t M i d t e r m Last First Middle April 26, 2004 Dr. Xi Chen TA_______________________________________ This exam contains 5 pages and 4 problems. When you are told to start, check to see that all the pages are there. If not, ask for help now . No adjustments will be made later. 1. (24 pts) Name (IUPAC system) or draw the structure of each of the following compounds. (a) 2-(Methylamino)propane (b) N -Methyl- N -propylbenzenamine (c) Benzylcyclohexylmethylamine (d) 5-Butyl-6-heptenoic acid (e) (f) (g) (h) Page Points 1 2 3 4 5 Total C O CH 2 CH 3 O CH 3 CH 2 CH 2 CH 2 O O O C O N CH 3 CHCH 2 CH 2 Br CH 2 CH 3 CH 3 OH O Cl
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Page 2 of 5 2. (36 pts) Write the structure of the major organic product(s) of each reaction shown below. CH 3 CH 2 CHCH 3 Br 1. Mg, ether 2. CO 2 3. H + , H 2 O a) ClCH 2 CH 2 CH HNO 3 b) O H 3 C c) 1. DIBAL* H 2 COC O CH 2 CH 3 2. H 3 O + * Diisobutylaluminum hydride d) Br 2 , NaOH, H 2 O O NH 2 e) N CH 3 1. CH 3 I 2. Ag 2 O, H 2 O 3. f) 1. CH 3 I 2. Ag 2 O, H 2 O 3. Product of reaction "
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Unformatted text preview: e " Page 3 of 5 g) 1. LiAlH 4 , ether O NH 2 2. H + , H 2 O 3. neutralize h) CH 3 CHCH O CH 3 (CH 3 ) 2 NH NaBH 3 CN, CH 3 OH i) CH 3 CHCH 2 CO 2 H CH 3 SOCl 2 j) Product of reaction " i " CH 3 CH 2 OH pyridine k) Product of reaction " i " AlCl 3 l) CH 3 CH 2 CH 2 CO 2 H Br 2 , cat. PBr 3 Page 4 of 5 3. (20 pts) Write out detailed, step-by-step mechanisms and the major organic product(s) for each reaction shown below. Be sure to show electron pair arrows for each step. a) 1. HCl, EtOH, 2. NaOH, H 2 O O + CH 2 O CH 3 NH 2 + b) O O O (CH 3 ) 2 CHNH 2 Page 5 of 5 4. (20pts) Write out efficient syntheses of the following molecules, using the indicated starting materials. CH 3 CH 2 CH 2 Br a) N CH 3 CH 3 CH 3 CH 2 CH 2 CH 3 CH 2 Br b) CH 2 CH 3 CH 3 CH 2 C OH CH 2 CH 3 OCH 2 CH 3 CH 3 CH 2 C O...
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This note was uploaded on 01/21/2012 for the course ECON 2a taught by Professor Xi during the Spring '11 term at Cornell College.

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first midterm 2004 - e " Page 3 of 5 g) 1....

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