whalen4 key - Name Q; fl, HOUR EXAM IV 1. (16, 4 each) For...

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Unformatted text preview: Name Q; fl, HOUR EXAM IV 1. (16, 4 each) For each of the following reactions, five peasible products have been given. In the box provided write the letter corresponding to the major product that would be expected to form under the conditions given. BE SURE TO CONSIDER THE STEREOCHEMISTRY OF THE PRODUCT YOU CHOOSE. r K+ar E ,c--....H > 3‘ OCHz \l CHa-CEN (aoetonitn‘le) CchHa CHZCHg CL (i: I /H CH2 /H , "'ruH ,C-u-uB _ \ H - A. OCH: \ B. OCH; \ r C. /C~C\ D. /C—C\ E. A1to1mixture Br H H CH20H3 H CH3 ofA and B Br «H E 9 > b Ucm 0°C Ml 0 ('3' CH3 (if xH 0"“...H CH CH #CH I \ 2 3 ..- 2 0-.” 0 . A. i B. C“ c. 1 ’H D. “13/” E.A1 to 1 mixture / CH3 3 of C and D CH3 H PO m c CHacHZHC.” —3—i—- L "OCH3 CH3 CH3 OH _ x ,r 3 CH3CH2 H CH3 CH3 (gt-13m2 OCH3 A CH3CH2 (i ~09 B CH30H2_T ( C >C=Cf 0- :0:c: E >020 .. _ I \ CH3 OI'T"HOH CHSOH CH3 H H CH3 H H Hour Exam Ma), Chemistry 301, Spring 200?. Page 1 of 4 pages cH3 d. CHa-CH:CH—c\:b JP N:;;H. @ NS 0 fCHg XCHS [CH3 yer-i2 A_ CHa—CHZCH—(ili B. CHa—CH:CH—Ctly c_ to 1 mixture DI CHg'CHZCH—C“ E_ CH3"CH1CH—$ "'si-i "’CH CH of A and B ct ci—iaoi-i2 HS 2 3 ,3, CH3 CH3 2. (7) Aldehydes may be converted to hemiacetals by treating them with ethylene glycol under acidic conditions. This problem will lead you through determining whether the oonversion of acetaldehyde to 2» methyl-1.3-dioxolane. as shown in the following equation. is an oxidation, a reduction, or neither. OH |_l H H \ I CH3—C-H CH3—C-H a El ii a :1 Ll bri b.:_ a. (4, 1 each) in the space provided beneath each carbon atom In the reactant and product, write the oxidation level of that carbon. in. (2. 1 each) In the space provided beneath each compound, write the net oxidation level for all three carbons In that compound. Your answer must be consistent with our answers to art a. c. (1) CIRCLE ONE. The reaction shown is an OXIDATION, a REDUCTION.our answer must be consistent with your answers to part b. Hour Exam Ma), Chemistry 301. Spring 200?, Page 2 at 4 pages 3. (12. 4 each) In each of the following chemical equations, the starting material has been replaced by a box. In each box, write the letter from beside the structure of the organic chemical shown below the equation that would be best expected to give the Indicated reaction. Be sure to CONSIDER THE STEREDCHEMISTRY REQUIRED FOR THE CHEMICAL YOU SELECT lF IT CAN BE PREDICTED. 1. BHa-THF CH3 CH3 3' C/ 2'H202‘IOH‘ 3 3H + H3 I 3 free of otherdiastereomers 3‘1“ CH3 CH3 ; raw/no D\ /D D\ /CH3 C113 / D HE:I\ /CH3 A /c=c\ B. CHg-CEC—CHs c. ,0:0\ I). ,C=C\ E. ;c-cl CH3 CH3 CH3 D CH3 D CH3 \"oD H F Bra Cl Br _ b. ——- free of other drastereomers OHZCI2 Cl Br I F W5 anti M30 F CI : H F F F Cl\ / Br 0—0 Homx h / CI 0—C/ CI\ /Cl A /C'c'-., B. / ' \ C /C C'». D / ‘ E. /C:(3 H F Br F \"c. F CI F F F CI 0H C C. A KOH "r A Smog H3 free of other alkene isomers CH30HZOH 3 ~CH3 Br Br ,CH3 A [CH3 B [CH3 C ems}! - elm/ch - CH3 cr-g - rim CH3 CH3 CH3 2 H0 CH '0“: m ’ 3 '1 Cmcfl E' CH3 I CF‘ICH CHa Br 3 Hour Exam Ma). Chemistry 301‘ Spring 200?. Page 3 of 4 pages 4. (4, 2 each) In the boxes provided. write the structures of the two starting materials that would be required to give the product shown by means of a Diels~Alder reaction. 5. (1 1) Multiply functionallzed. radiolabeled compounds are valuable for medicinal chemistry research. Below is summarized the synthesis of such a compound. In each box, write the structure of the compound that would result from that synthetic step. REMEMBER: Each structure must be the product of one step and the starting material for the next step. The number in each box is its point value. 0 O \l + / __é . CH NaBH4 CHaoH l H \ CH30H (2} soon;r pyridine D 0:0/{H1Cl Lindlargs cat. W1“ D Mg; (2) {1) ether D D mil—314 Br2 I hv D : D (2) (2) Hour Exam “3(a), Chemistry 301, Spring 2007. Page 4 of 4 pages ...
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whalen4 key - Name Q; fl, HOUR EXAM IV 1. (16, 4 each) For...

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