Practice Exam 1 Key - NW Exam 1 Tuesday, October 27, 2009...

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Unformatted text preview: NW Exam 1 Tuesday, October 27, 2009 Answer as many questions as you can in the time allowed. Please be as clear and concise as possible. 1. Zestn'l is a bestselling medication used to treat high blood pressure. a. Identify all the functional groups in morphine. Classify as primary, secondary, tertiary where relevant. b. Identify the most acidic site and the most basic site in Zestril (if more than one will be about the same, indicate that). Justify your choice. M05} Linda: m in,“ Wm‘my MOS) 5C;flt‘c‘. m iv.) )1 (off flu xyllfl 75M 30’ 2. Ethyl butyr : . : compound that smells strongly of bana a. Ethyl butyrate is somewhat acidic. Draw its conjugate base. b. Ethyl butyrate can be deprotonated with NHz‘. The ch for this reaction is 10"). What is the pKa of ethyl butyrate? What is the AG for this reaction? pKa (NH3) = 35 pKa (NH4+) = 10 3a. For each of the following compounds, draw the HOMO and the LUMO (make sure it’s clear; use separate drawings if necessary). >=o % > b. For the first two compounds above, which has the higher HOMO? Which has the lowerLUMO? i” ARI )1 1m; [aw 4. Rank the following in order of increasing boiling point: 0 o i 1 OH l: > (\O I >-———0H J O O O OH 1 S I L] 3 D l (non/Max) ZH/Lm/J 462;]: POL? I [Tl/4" gal {WI/eff 5. 1,2-Ethanediol (also known as ethylene glycol) is commonly used as an antifreeze. Draw 1,2—ethanediol as a line drawing. Draw Newman projections of all possible conformations. (There are 4.) Rank them in order of stability. Surprisingly, the anti conformation is not the most stable. Why? (M W 0” ' '7 6. Identify all the isomers of l,3,5-trimethylcyclohexane (excluding mirror images). Draw both possible chair conformations of each of these isomers. Rank the conformations in order of stability. Which isomer is most stable? 7. Name the following compounds according to IUPAC rules. 3,7’0’1Mi/‘7ioci‘0l ’Zié when ’i’0( ’éfoMO aychoen iyi)’t{’nM%7/c)'O/Ofiefrm 8. Rank the following compounds in order of pKa (from lowest to highest) /8“ /\/\OH /\fl/SH /\U/ 0 Z 2 I L/ [QM/2ft!" 5x 9. You have isolated a compound A with the formula C6H8. In its '3 C NMR spectrum, there are 2 peaks. Upon hydrogenation, a new compound of formula CGHIZ (B) is formed. This new compound has only one peak in "the “C NMR spectrum. A different compound C of formula C6Hlo also gives 8 upon hydrogenation. How many '3 C signals does it have? Identify all three compounds. pd/C Pd/C A B C Cans CGHn C6Hl0 2 ‘3C signals 1 13C Signal 3 7. l3C signals 10. Rank these in order of increasing Lewis acidity: CH3+, CBrf, CF3+. Be sure to briefly justify your choice. ‘ ml l- l“ Ing“d’k%<fifiwféfi C ‘3 P G 7 3 C C We: liq a $445 ...
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This note was uploaded on 01/18/2012 for the course CHEM 335A taught by Professor Michael during the Fall '11 term at University of Washington.

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Practice Exam 1 Key - NW Exam 1 Tuesday, October 27, 2009...

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