3_22_2000 key

3_22_2000 key - NAME KJEY CWEMISQWI 30$ (B.H. Lipshutz)...

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Unformatted text preview: NAME KJEY CWEMISQWI 30$ (B.H. Lipshutz) finalfixam Marc/i 22, 2000 56 2. 20 20 3. 2O 20 4. 9+20+5 34 5. 10+4+4+10+4+4 36 6. 6+10+3+5+10 34 l iZOOI 1. Predict the major organic product from each of the following. Indicate stereochemistry where appropriate. (a) H LDA M W H " L ' r ______._—-> D 0 O 2. D20 (b) I. “5" —_.—————-——--——-—D 2. CO7. Bl’ Ho" Hzo (C) l- H30+1A ____..__—-—-———’ 2. E‘l’oH. “1:11 H" CN 002/61’ (d) . . ,H L Tones ax:de ________———-9 N @‘OH 2. HzNon, mi. H” 6: \DH (rad/mic) (e) OX0 l. n—BwUIWF.9o 0X0 ___..___———————v g 5, z. 21"?” /\/\/\\/\ 3. Na/liq. NH; ,’33’ (f) MK I. ‘ZPWIW? m4 = / OH 2' PM? C‘Iflc % (g) H H I. 621%, W on \ H 3. BZHL, M (h) H 0 I OH I— walw @A/km z. CHLNZ, 647/0 2. Starting with n-octanoic acid, devise a short route to the eight carbon nitrile 1 below (which does not involve a dehydration step). steps NWCOOH /\/\/\/CN 1 1. kh)‘ Ml 12 A3 M03 T m1, 9MP WOOZM Wm M“ ( ansdtm mm.) 3. Starting with any alcohol of five carbons or fewer, and using any reagents of your choosing, devise a concise synthesis of alkene 2 below. WW fhstCflz CH2 2 /\/\/0H “LMS --—-———92 New ' M 60014 W mm, ("7” WM") 0 J nrflvu {— /\/\ 002 :1 Hw 4. Compound 'X' gives the following IR, NMR, and MS data: MS: m/ e (relative intensity) 136 (M+, 14), 134 (M+, 42), 99(100), 65(5), 63(15). WAVENUMBER CM" E%§§E§Et§p. aggg = §%§%§§§Eamrwwfi g$§§fifififififififigfififi sfi§fifigfi§fifig“fi l ., l ; ,EEEE§%-§%%%§§E$% .EEE§§%E§%§%§Q$§ ., .; é; lg H A . tegfigggggegfim * :2 i gt image; m at“ mmh um (a) Label at least 3 characteristic peaks in the IR spectrum. (b) From ALL of the data given, suggest a structure for 'X'. (c) Give the structures and charges for the five peaks observed in the MS of 'X'. (0H3 on); OH 00017}? 134 (3%) 34, (“to 7+ (war/#2,); 0H?!» 01‘? 0 c— all 65 (gal 2 as (“an 5. When alcohol 3 is oxidized with PCC, product 4 results. This new compound 4, when subjected to oxidizing agent MCPBA, produces product 5. Product 4 reacts with LDA followed by TMS-Cl to give new product 6. When 4 is exposed to LAH, two compounds 3 and 7, are generated. H o 0 FCC MCPBA 3 4 5 1. LDA/ 2. TMS-CI \LAH . H 05mm g“ + 6 7 3 (1) Provide the structures for products 4 and 5 in the boxes above. (2) Suggest a structure for the new product 7 formed upon treatment of 4 with LAH. (3) Provide the structure for product 6 in the box above. (4) Suggest a mechanism for the conversion of 4 to 5. 4 " 1/“. f? “ 0 ovffi'fir 0 Ho—o-L'Af 0 ——-—~» fifi ———- q? + W a K K lac/lime (5) What functional group is formed in product 5? What functional group is formed in product 6? (6) Provide a 3D orbital picture for the functional group in 4. 6. The kinetic aldol reaction between 4,4-dimethyl-3-heptanone and cyclopentanecarbaldehyde leads to two products, 8 and 9, of identical molecular weight. 0 1. LDA, THF, -78° 2. owe the ketone the aldehyde (a) Provide structures in the boxes above for the two starting materials. (b) Provide structures for products 8 and 9. (c) For products 8 and 9, comment on the relationship between them: didamm (Stan ¢ M“) (d) If 8 (or 9) is exposed to KOH in D20 at room temperature, what is the expected reaction outcome (i.e., draw the product in the box above; assume no reverse aldol occurs). (e) Provide a mechanism for the overall conversion to either 8 or 9. ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.

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3_22_2000 key - NAME KJEY CWEMISQWI 30$ (B.H. Lipshutz)...

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