EX12BF08_3_practice_answers

EX12BF08_3_practice_answers - ORGANIC CHEMISTRY FALL 2008...

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Unformatted text preview: ORGANIC CHEMISTRY FALL 2008, LANEY COLLEGE CHEM 12]} (Ll/LIL, 41830/41832) INSTRUCTOR: S. CORLETT Exam 3 Practice Page 1 of 5 NAME QQM l. The product from the following reaction is an acetal. Show the product and the complete mechanism for its formation. (10 points) m (43>. » '* “ H0 ‘3‘ o a» i ‘ ‘ar —~ X H? >< fwd ‘ “M W a ‘4 a /(b\\ {H\Oi“®l L0 , l filmlfi')’ H9 @bm ~14 HE " j m m m w»— ~><W a ray 2. Show the product from the following reaction. (5 points) PCC ' ' CHZCIZ ‘ it u 3. Provide reagents to accomplish the following transformations. (10 points) a ' OH w” W'“» Mfllfif ‘ O 3 HO CHO __, ___,, W/Y 59 M Q} "l 2 M2 3 ORGANIC CHEMISTRY FALL 2008, LAN EY COLLEGE CHEM 128 (Ll/L1 L, 41830/41832) INSTRUCTOR: S. CORLETT Exam 3 Practice . ' Page 2 of 5 4. Provide IUPAC names for the following compounds (don’t forget stereochemistry where appropriate). ‘ (15 points) 0 O . . F o . NH2 a. W b. H c. m CCl3 , suswmww~ «WWW/c w-I'wa . WWW , M‘SZ’W.~1W Q~M173MW 5. Draw the structure of the following compounds (don’t forget about stereochemistry). (15 points) a. 2-benzyl-3-oxopentanal 4;? ‘5? W\ H P b m3, b. (S)-4-(1 -fluorocyclobutyl)pentan—2~one F $3 )\ /\ c. (R)—3-methoxy-N~ethylhexanamide ' H WWWW 1 N A 0.... a W _. w» 2: H W W WM“ "" , oc’u3 «firm CA 2 I 6. Show two (2) different methods to prepare the product shown below starting from a nitrile (not the same nitrile for each method). \ (10 points) ORGANIC CHEMISTRY CHEM l2B (Ll/LIL, 41830/41832) Exam 3 Practice FALL 2008, LANEY COLLEGE INSTRUCTOR: S. CORLETT Page 3 of 5 7. Show the product (or products) from the following reactions. (20 points) 0 t 1. LiA1H4, ether Cf”! M ——»y 2. H3 0’ ' 1'1 H bl N x \ M fi. u / / cat. p—TsOH A 0 H2 M Pd/C / o . i? at. / 2. (CH3)ZS / \ng * C) \ i O Explain why the top equilibrium favors the starting materials and the bottom equilibrium favors the product. - (Note that both starting materials are ketones.) (10 points) + #3 with .95 i + H20 H HXH mtg; W chzl-4X10_3 W ‘ ' s ‘ ' W m array MM W033?) ' H+ HO OH WM SW» W37 ClQK/Cl “9/ “‘20 W) m ‘ W2? “4044? M' v H 4f/ngj «L flfiml'gimté’ ‘W M W M “9/ 7 l"\ P4ng gnaw-flu f5 ORGANIC CHEMISTRY FALL 2008, LAN EY COLLEGE CHEM 123 (Ll/LIL, 41830/41832) INSTRUCTOR: S. CORLETT Exam 3 Practice ' Page 4 of 5 9. Show the products or reagents necessary to accomplish the following. 0 /> H3O+ ll? 9H} 0 , a- Y H + H o N M‘N/ (2 products) 0 f l t L’, (t8w033/H H O 1, H11, P 19 CN . N/\ c ——> I ? ’ Cf L H (L) 3 ’a l LF/ 1"; r I; H3 0 "l' O i l I d ~ H —> W M N A ORGANIC CHEMISTRY FALL 2008, LANEY COLLEGE CHEM IZB (Ll/Ll L, 41830/41832) INSTRUCTOR: S. CORLETT Exam 3 Practice ' Page 5 of 5 10. Mescaline is the psychoactive active ingredient found in Lovhophorawilliamsii (Peyote). Devise a synthesis of mescaline starting from gallic acid. ‘ (10 points) HO C02H H3C0 NHz , («z-z , ———> "7e HO ‘ H3CO . U h, ‘ OH OCH3 x 0-wa3; v allic acid mescaline CH 0 am? , g ' 3 w, \cgsM ‘ Cu * M.) .' D \i , 0W3 M an . \ LLIPKH’W ' Wag, jMoCN a? 0% ml) WED \ /\ FEW “J \ / \A «XE . an H s W . r Q My out 11. The proton (1H) and carbon (13 C) NMR for Compound A, with formula C9H100, are given (see the website), along with some partial data from the spectrum. 1.40, d, J: 7.0 Hz 3.65, qd, J= 7.0 and 1.5 Hz 9.70, d, J = 1.5 Hz (Note the three small peaks at 77 ppm in the 13C NMR is from the solvent and is not part of the compound) Compound A when heated with hydrazine (H2NNH2) in the presence KOH gave Compound B, a hydrocarbon with molecular formula C9H12. Also, when Compound A was treated with solution of Jones” reagent (CrO3, H2804, acetone/HO) the solution turned from orange to blue/green. The 1H and “C NMR spectra for Compound B and some partial data are given below. 1.25, d, J= 7.0 Hz 2.90, septet, J = 7.0 Hz What are the structures of Compound A and Compound B? ...
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This note was uploaded on 01/23/2010 for the course CHEM 12B taught by Professor Corlett during the Fall '08 term at Laney College.

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EX12BF08_3_practice_answers - ORGANIC CHEMISTRY FALL 2008...

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