Chem 317 - exam 1 key

Chem 317 - exam 1 key - CHEMISTRY 317 - WINTER 2008 EXAM I...

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Unformatted text preview: CHEMISTRY 317 - WINTER 2008 EXAM I — Thursday, January 31st NAME: K5 7' (last) (fiYSt) 1. This exam consists of 5 questions. Do the ones you know h come back to the others if you have time. 2. Please, do your own work! Some Common IR Abso . tions MAKE SURE YOUR EXAM HAS 8 DIFFERENT PAGES INCLUDING THE COVER Name: E y 1. Circle the correct response for each of the following: (2 ea) > a) Which of the following compounds is expected to have the highest b'ling point? A/ kc». L g A b) For which of the compounds is the proton labeled Ha expected to be the most deshielded in the 1H NMR? /\/Ha /\/0Ha 0/ O c) Which of the following is expected to be the most . 'dic? /\/\OH \AOH C'WOH d) What splitting pattern do you expect for the proton labeled Ha in the compound shown below? V”: Ha - - \ 0H Singlet doublet triplet doublet of quartets doublet of triplets pentet doublet of doublets none of these 0 e) Secondarykalcohols can be easily oxidized to which of the following? alkenes aldehydes esters carboxylic acids amines f) Which of the following pairs is expected to have the largest coupling constant in the molecule shown? Ha \ Hb Br Ha-Hb Hb—Hc Hc g) An ester can be converted into a primary alcohol by reaction with which of the following (if followed by workup with water)? a grignard reagent RLi sodium borohydride none of these h) The intensities for the individual peaks in a quartet are expected to be in the ratio: l:1:1:l 122:2:1 l:2:3:1 1:4:421 none of these Name: 5 E Y 1. (continued) P i) Which of the following compounds is expected to react fastest with Mg in diethyl ether? NE” - /\/F /\/C' j) Which of the following is typically used as an oxidizing agent? HZ/Pt HBr LAH k) Which of the following will change upon going from a 60 MHz NMR to a 300 MHZ instrument? integration coupling constant chemical shift 1) Which of the following reacts fastest with the Lucas reagent (HCl and ZnClz)? $/t/ /°\/ k/o” ‘ m) How many signals (don't include splitting) is the following compound expected to give in the 1H NMR? 1 <2) 3 4 5 6 none of these 0 11) Which of the following is not expected to react with chromic acid to ive a green color? OH ,3 KEY Name: 2. Complete each of the following reactions. If no reaction occurs, write ‘No Reaction’: 0 0 ma eh m 0 OH I) (.‘H3CH2MgBr b) \ —__h M 2) H+ /H/\/OH PCC‘ a} _—_—"" O H o d) HJ‘LOR t} 0 2)/\/0T5 Q S Name: Y 2. (continued) 2 g) X/k/OH Mater“)? h) D40}! excess H2, Pt N o H 1) TsCl, pyridine j) 2) LAH fl ———’—‘——-—* A 3) H20 OH 0 o k) 1) LAH _————————> o 2) H20 0 1) :f/ 5; HO 1 1) CH3CH2MgBr ——-——-—_—> 2) H20 Name: ’1 3. Shown below are the 1H NMR's for two compounds. Compound A has molecular formula C6H1202, compound B has molecular formula CSHIOOZ. Provide a structure for each that is consistent with the NMR given. Both compounds also have a strong absorption around 1700 cm‘1 in the )3 Name: KEY 4. a) Using correct arrow formalism, show the mechanism for the following P transformation: f 1) /\Mgl (2 equiv), Et20 MM” 2) H20 workup Mu?’ “,3, J’ AWL p’ /9 o b) Suggest a way to synthesize the compound shown below (the alcohol), using the alkene shown and whatever other reagents you need. You do not need to show mechanisms, but make sure you Show all reagents needed and the correct order of addition. OH Q make this /7 H * Pa. C"; U .———--‘9 .——> \ "" 7 O' \s :4 Lo L. 0 0H Name: y P 5. a) Determine whether the pair of H's in bold for each of the following are homotopic, enantiotopic, or diastereotopic: H \ x 5 H . b) Draw the structure of a compound with molecular formula C4H100 that would give two singlets in the 1H NMR (and that's all). +014 ...
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This test prep was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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Chem 317 - exam 1 key - CHEMISTRY 317 - WINTER 2008 EXAM I...

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