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final%20exam%2008May11 - Name Spring 2008 4:122 Final Exam...

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Name_____________________________________ 1 Spring 2008, 4:122 Final Exam 1) Draw the indicated structures and reagents. No mechanisms. [3 pts each box] a) Two different reactions of 2-propanone (i.e., acetone) that EACH produce a different alcohol. b) Two different aldhydes or ketones that will yield 3-methyl-2-pentene via a Wittig reaction. Show EACH starting material and Wittig reagent. c) Two different carbonyl-containing starting materials that will yield 3-pentanol via a reaction with an organometallic reagent. Show EACH starting material and organometallic reagent. d) Two different carbonyl-containing starting materials that will yield butylamine CH 3 CH 2 CH 2 CH 2 NH 2 upon reduction. Show the carbonyl containing starting material and reducing reagent. 2) Enter the requested data into the table for each structure at the top of a column. [1 pt each entry] number of p orbitals in pi system number of pi electrons in pi system aromatic, antiaromatic or neither
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Name_____________________________________ 2 Spring 2008 4-122 page 2 of 8 ____________ 3) Select the structures that are consistent with these spectrocopy data: strong stretch between 1750-1700 cm -1 ; no broad peak(s) between 3200- 3400 cm -1 ; one medium peak at 2252 cm -1 . [3 pts] A H 2 NCH 2 CO 2 CH 2 CH=CHCH 2 C N D 3-methyl-4-pentyn-2-one B CH 3 O 2 CCH 2 CH=CHCH 2 C
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