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Practice Prelim #2 key

Practice Prelim #2 key - K NAME KEY ~ CHEMISTRY 1570...

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Unformatted text preview: K) NAME KEY . - ~ CHEMISTRY 1570 Summer-2009 Wednesday, July I5, 2009 11:00 am. — 12:30 pm. PRELIMINARY EXAM #2 Please-do not open this exam booklet until you are told to do so. You will have, 90 minutes to complete the exam. Page # '1, . (20 points) “:3 ' _ ' 2, ' '4 (15 points) 3. _____'_ (15 points) 4_ ' . (15 points) 5, l - (15 points) 6. I (10 points) I 7. I. (10 points) TOTAL (use Excluding this cover page there are 7 pages in this exam. 1. (10 points') Thereaction of (S)-2—bromobutane with sodium hydroxide follows a second order rate law (the rate is dependant upon the concentration of two reactants) and gives . 2-butanol as the major product. Show a mechanism consistent with this rate law using the curved arrow formalism. Show the transition state(s) and/or intermediate in brackets and draw the relevant stereochemistry of the product(s) showing the R or S designation. 8 , cacti; - 6 Kl/ 6; “a H J \ .5 CH? 1 ~-——? CHCHLHC/‘fic/H ._.__—.———> C/ "J / V‘H 3 g 2: 3 R I (Lu 5 4 .. 3 OH Oil NC? El": . (a - , . I @ 0H WJWV I 5N2 Maw I 2. (10 points) The S‘NZ reaction in a Williamson ether synthesis can occur intra—molecularly, meaning within the same molecule. What product would yOu expect from treatment of 4wbromo-1-pentanol with base? fl ' I P . . Br-gHchch2CH2CH2-0H + BASE _), yaw \. " L | l l l I Page 1 A Q 3. (‘l 0 points) 4. (5 points) Please show the mechanism of the formation of a gemdiol resulting from an acid catalyzed reaction of acetone with water. /"7{7L* )2 H20 \ _ H30 CH3 H+ catalyst k/T (9/14 0’6"! 1 O’H 390% 1 cl; all 4 E CLl ll <——> G ~——;>CH,*‘ ‘" g, cH~ ”’ - Cit/G\ ell/@Ya 6:» tr e“ 3I 3 3 Cit-l 3 . 5 06 0M 3 fl) 5% ,@\“E :OAH t ‘ ( What are the major products of this reaction? Is the reaction SN1,SN2, E1 and/or E2? Please draw the molecules and label any asymmetric carbon with the correct R or S designation. HO 6M3 (\\ 5. (10 points) . /‘ How would you carry out the following transformation? More than one step may be required. You do not have to show mechanisms, but please indicate any required reagents or special conditions. ' 3? Bl’ : C\CH3 ME I HLCVL07 um OH O \/ ll' ’ (Erma /\ Vi Br DCHS . . . M .) > \J 2) llso" 6. (5 points) . . , Please show the reagents and conditions required to bring about the conversion of cyclohexanol to the following aldehyde. 7. (10 points) In the commercial synthesis of methyltert—butyl ether (MTBE), and antiknock, octane—improving gasoline additive, 2—methylpropene and methanol are passed Over and acid catalyst to give the ether. Propose a mechanism for this reaction. QHa + I acid'catalyst I 9H3 HsC-CfiHzH L CHsoH _‘*—‘* Hsc—CII-O-CHs 2-methylpropene methanol _ CH3 GHQ, Li Y methyl tert—butyl ether (MTBE) l ,3 l . . _ s /r’ u c €91» CH z Q a i 4 Q; '~ 6 CH \ t. L 3 f 3 l4 _ 0 " CH3 @O Na! ' - i4 \7‘ 3 ‘8. (5 points) Draw; the structural formula for the product of this 8N2 reaction. H28r + NaCN ——> Q/CHZ’CN ‘y/ Page 4 hI 9. (:0 points?) “w ’ For each of the following pairs of compounds, say whether they are enantiomers, diasteIreomers or meso compounds (same compound). (a) CH5 CH3 Warqurganal is a crystalline solid that acts as a plant growth regulator and has cytotoxic, antimicrobial and molluscicidal properties. Label each stereocenter with an asterisk and specify the number of stereoisomers possible for this molecule. ' i . .4. ‘ I ‘ 9. :léWLe/w l . Page 5 10. (5 points) Show the structures of the alcoh0l(s) and aldehydes or ketones you would use to make the following acetal: .0 Ce” ' "iii: reo/ 0W” ouceioti 11. (5points) Please indicate the reagents needed to complete the following transformations More than one step may be required CH3 30(327 (PHs CHs-dIZHCHon ' ’ CHs-CHCHaCl l i I l l O 12. (15 points) w Please-complete these reactions showing the major product(s) and include stereo- chemistry if relevant. . I I ' I (W3 m» No Rethzem CHa-Cl-CHZCHa . OH Hso+ if? —-—--—-—> 2.) W H o ' ‘ CA . C‘H 1.) Ag<NHa)2+,0H t/Y 0H ’43 \/ /> 014 V 0 1.) LiAIH ‘ . n 4 , ‘ CHa-CHgC-CH‘a‘ ——————> C1—C3 CHZ , 051‘ CH3 _ 2.) -H30* , H HaC __ ,H 1.)NaBH4 H3 C \ / >C—C C : C HsC '—H 2.) H20 / \ o H to CH DH . 3 _ Z ,0 H 0w CH3-CH-CH2-CH3 2.) H30 + 3 LI) . Page 7 ...
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