Chem239A Exam#2 - (c) Starting from heptanedioic acid (HO 2...

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CHEM 239A Summer, 2009 EXAM #2 Name . Prof. Sasaki 150 points TOTAL Good Luck! Note: Only answers in the box will be graded. _______________________________________________________________________ 1. (35) (a) Rank the following compounds in each set in order of increasing basicity (indicate “1” for the most basic amine, and “3” for the least basic amine). (i) NH 2 NH 2 NH 2 F 3 C H 3 C (ii) NH 2 NH 2 H N O CH 3 (iii) NH O NH O (b) The compound shown below is somewhat stronger base than ammonia. Circle the most basic nitrogen in the structure, and provide a brief rationale. N N CH 3
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CHEM 239A page 2 Name . 2. (40) Consider ethyl (2-oxocyclohexane)carboxylate (shown below), and answer the following questions. O O OCH 2 CH 3 (a) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate. (b) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2- methylcyclohexanone. You may use any reagents that you wish.
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Unformatted text preview: (c) Starting from heptanedioic acid (HO 2 C-(CH 2 ) 5-CO 2 H), propose a reasonable synthesis of ethyl (2-oxocyclohexane)carboxylate by a Diekmann cyclization. You may use any reagents that you wish. CHEM 239A page 3 Name . 3. (35) Predict the major product(s) for each of the following reactions. If more than one product is expected, please put all of them in the box. (a) NCH 2 CH 3 O 1) LiAlH 4 2) H 2 O (b) (CH 3 ) 2 CHNHCH(CH 3 ) 2 NaNO 2 HCl, H 2 O (c) CH 3 N(CH 3 ) 3 OH H 3 C H 3 C 160 °C (d) H 3 CH 2 C O CO 2 CH 2 CH 3 CO 2 CH 2 CH 3 H 2 O, H 2 SO 4 heat C 7 H 12 O (e) O OCH 2 CH 3 OCH 2 CH 3 O O Na 1) 2) H + / H 2 O CHEM 239A page 4 Name . 4. (40) Propose a reasonable synthesis for the following transformations. You may use any reagents that you wish. (a) CONH 2 CONH 2 Br-CH 2-CH 2-Br (b) CH 3 H 2 N O 2 N CH 3 Br F...
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This note was uploaded on 01/19/2012 for the course CHEM 239 taught by Professor Sasaki during the Summer '06 term at University of Washington.

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Chem239A Exam#2 - (c) Starting from heptanedioic acid (HO 2...

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