exam3s09 - Chem 273 Exam #3 April22,2009 Lastname Firstname...

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Chem 273 – Exam #3 April 22, 2009 Last name First name This exam contains 9 questions and 5 pages. You have 50 minutes to complete the exam. All papers must be handed in by 10:20 A.M. You may use molecular models to help you answer questions. Do not spend too much time on any one question. 1. (8 points) Answer the following questions on nomenclature. a. Draw the structure of N -isobutyl- N -methyl-2-ethylbutanamide. b. Give a systematic name for the following compound. H N 2. (06 points) Ignoring E,Z isomers, draw all mono enol tautomers of the following compound. O O
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Chem 273 – Exam #3 - 2 3. (24 points) Draw the organic products formed in each of the following reactions. [2] H 2 O a. b. c. d. e. f. NaOH, H 2 O O O O CH 3 CH 2 NH 2 (excess) + CH 3 CH 2 O CH 2 CH 2 CN [1] CH 3 CH 2 CH 2 MgBr O [1] Br 2 , CH 3 CO 2 H [2] LiBr, Li 2 CO 3 , DMF CHO NH + NaBH 3 CN O HCO 2 Et + [1] NaOEt, EtOH O O O CH 2 CH 3 [2] H 3 O + 4. (08 points) 1-Methylcyclohexene can be converted to 1-acetylcyclohexene by a two-step reaction sequence. Identify intermediate A
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exam3s09 - Chem 273 Exam #3 April22,2009 Lastname Firstname...

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