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51finalF07 - Chemistry 3351-100 Organic Chemistry Dr Barney...

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Unformatted text preview: Chemistry 3351-100 Organic Chemistry / Dr. Barney Ellison Thursday: Saturday, 15 Dec., 1:30—4:00 PM/ Final Exam/ Chemistry 142 Name: Kflé (please print) 1. (10 pts) 3,3, S-Trimethyl-l-methylenecyclohexane reacts with 3- chloroperoxybenzoic acid mostly the diastereomeric epoxide shown. However, when the same alkene is treated with Br2 in water and then with alcoholic base, the other diastereomer is the major product. Draw the structure of the second diastereomer and explain the results. 2. (20 pts) -2- Show how each of the following conversions can be accomplished. In addition to the starting materials, other organic compounds can be used as necessary. if HC=CH CHSCHQCCH3 + Rm ”1 \LNQ z. .. 604 Mac: + Carer A5 who \ BLEDR V )3’ ..-C gC—CQLCR; CH300H20H20=CH —-—- CH300H20H20H20H20N HCECH —-—1- CfS—CH3CH2CH=CHCHQC H3 \(J Na NHL 1+ N HCO“ + afiw EEK Q] £95014; \ CM“) Rec—ax 1 mm (m /L “W wav— ( W" \ mm A CR5 W 9‘5 6" :C “CH ——§ .— er H .1. Freon 0'“ng CH CH; (:13 \ajfio V 61% CH} \ CH—“CHzmz, 3. (20 pts) -4- Show how the following compounds can be prepared from alkyl halides and alcohols containing 4 or fewer carbons. ><°“/\/ /\ \ 7: 0 +~ NBC“ J‘S‘Lw‘iv ngu f M‘s» L\\LC\\2C\\[email protected] N\“/\\/ \k/‘PCC C) 1‘ cm /\\/ .\— /'\/ é‘” QRSCH (“J-CHZMQ E)?" -6- 4. (10 pts) Acetaldehyde reacts with (R)-1,2 propanediol to give two isomeric acetals. What are the structures? '1‘ Lg _ _. s v—D “‘40 thscfio 4— Gus (,1 c 20H OH (323 Gilt l~\ Clxloh O Hoe“Z A CE)“ 0}“) + H0 N CH3 '\‘ 0 _—— Q\~\ 2 CD“ CA7. O p. \ / ..- CH A I C" A / 3 n I / V n Q\\5"CIH Ho 05?; a ‘3 0“” 4r it no ;%L\(~\ Z '7 {O \C‘” H I‘v f \704 u - 01“ h ”grim; ¢U§K 0/ g 5 Ho? 3 N5 (\x -7- 5. (20 pts) Show one can accomplish the following conversions in a practical manner using any necessary organic or inorganic reagents. HO CHO ,9H3 A/ .3” CH3 CH a. Q“? 3 TNT \ Vang} ”13‘5"" //7 MO tug F O 1 6H; WH 6. (20 pts) What is the product of the following reactions? at. CH3CH2CHO + KOH/ H20 4- A --I- ? c A , 5 H _... C 3 C Q“}C 2.. y \ CARD H O KOHIHQO + (CH3)3C'CHO —"_"‘ A b. (k -10- (CH3)2CI-I-CI-IO + N aOH/ H2O (5° for 5 hours) —=v ? '51 I 1) CH3CH2COCH2CH3 + 1 eq_ LDA .4, (1H 3C R2:— c :C H C H} 2) addition of 1 eq. CH3CH2CHO —» (j K“) 3) work up with H20 -—1 ? (—j C H.520 p -— CH Q \x cm ——C 3 \ CR~OH -11- 7. (20 pts) What is the product of the reaction of 4,4-djmethy1cyclohexanone with each of the following? a. 1) LDA in THF —5- 2) CH3CH2Br —» ? (P /C A L04 l b. Br2 in CH3COOH —» ? C6H5-CHO + NaOH/HZO —» ? O /”\\//CH"/<:\) K/ /\ NaOD in D20 @ 25° —> ? OD 33:55]) /\ -12- -13- 8. (10 pts) When a mixture of an aldehyde or ketone and an a-halo ester is treated with a strong base, and a, B-epoxy ester is obtained. Propose a mechanism. 0 NaNH2 O 0003 A + CEACOOEt —“" H J, 0; (1W: / CQ / ) “02+ 19L ’5 5; (X /\ Cd) [j I “‘1 Q0033? / UN HQFCD \ A C C“; 9‘ w UL— c/ -14- 9. (20 pts) Each of the following can be prepared by an intramolecular aldol condensation. Show the precursor in each case. 0 -15- ...
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