whalen2 2008 key - Return my exam in class Return my exam...

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Unformatted text preview: Return my exam in class Return my exam in Ctark 278 NAME V MA 61 HOUR EXAM I! ‘I. (14) Name the compound having the structure shown. In your name, be sure to include the correct stereochemicai designation for any chiral center using the R/S system. IN NAMING A CHIRAL CENTER, YOU MUST SHOW THE PRIORITY (highest priority = 1 or a) THAT YOU HAVE ASSIGNED TO EACH GROUP. THE CONFIGURATION YOU GIVE MUST BE CONSISTENT WITH THE PRIORITIES YOU ASSIGNED. DO NOT ASSIGN PRIORITIES TO THE GROUPS ON ACHIRAL CARBONS. A Qeriodic table is rovided at the end of the test. (5 (9 CH3 (5,22) H30 Br @ , r Fz-CH a0, @ U \C 3 ’ H® H ljvf H» H30 CH3 \, \WWD Hour Exam II (a), Chemistry 301, Spring 2008, Page 1 of6 pages 3. (22) Tartaric acid is one of the main acids found in wine and is added to foods to give them a sour taste. A Fischer projection of one of the two enantiomers of tartaric acid is shown below. In part a of this problem, three structures are given that represent possible stereoisomers of tartaric acid. This problem will take you through the process of determining the stereochemical relationship of each of the three structures to the given enantiomer of tartaric acid. COOH a. (15, 5 each) In the space below each of the following structures, draw a H OH tartaric acid Fischer projection of the same structure that has been arranged with the Ho H two COOH groups at the top and bottom so that it can easily be compared COOH with the structure that is given to the left. HOOC H OH 6‘ l Hz..\ / HO C OH {i ‘ChC -_—-—7/ ol’ Ho OOH HO \ ’H ix H t/ COOH a,“ H a “9* 00H : ‘ H 60“ a H u tl H l H H {MM/thaw 00H b. (6, 2 each) Beneath each of the structures you drew in answering part a above, tell whether your structure represents the identical compound as was given for tartaric acid at the beginning of this problem, is the enantiomer of that compound, or is a diastereomer of that compound. REMEMBER: Difi‘erent conformations of a compound that can be interchanged by rotations around single bonds are not considered to be different comgounds, c. (1) One of the structures you drew should represent a meso compound. Circle the structure you drew that represents a meso compound. Hour Exam II (3), Chemistry 301. Spring 2008, Page 2 of6 pages 4. (30) a. (4 each) For each of the foliowing reactions, predict the major product that would be expected to form under the conditions given. BE SURE TO SHOW THE STEREOCHEMISTRY OF THE PRODUCT IF iT IS PREDICTABLE. b. (1) Teli by what mechanism (8N1, 8N2, E1, E2) the product is most likeiy being formed. 1 I CHngEcle Na® C-wuH ’- 8. CH CH/ C:C'*OH CH CH 3 2 \H DMF @ CH3 2 2 5 Mechanism 6512 CH3CH2 O Ui- abut H30 Ox“ 5 / j b ere-66 \tx - 2 CH3 :‘ Mechanism Br, H CI CHSOH i“? (MUCH : Cu“ (7-H (rota/W65) Mechanism 3 __ d W103 KOHIA } ' CH3CHZOH Mechanism OH _ ...uH I r e. O, 4 l Mechanism C)“ zCH3 %/ f H\ 53’s?) 99 x .9 K CEN / CH3CH2/ \CH3 HMPA 3 3 Mechanism 63/ Hour Exam II (3), Chemistry 301, Spring 2008, Page 3 of6 pages 5. (10) The reaction of the tertiary bromide below with methanol produces a mixture of products. Write the steps in the mechanism for this process. Be sure to show the following: (1) the structure of any intermediates that are formed during the mechanism, (2) what, if anything, is added or lost during each step ofthe mechanism, (3) any non-zero formal charges found on the structures that you write. REMEMBER: You ma not use an materials exce tthose that are iven in the e uation. CH/l .. CH3 OCHs gr. CH39H .. ' —-——a— OCH3 + CH3 + HBr Rx “k / Q) Gr, Hour Exam !| (a), Chemistry 301, Spring 2008, Page 4 of6 pages 8. (12) Heating the tertiary alcohol below with sutfuric acid produces the tetrasubstituted cyclohexene as the major product. Write the steps in the mechanism for this process. Be sure to show the following: (1) the structure of any intermediates that are formed during the mechanism, (2) what, if anything, is added or lost during each step of the mechanism, (3) any non—zero formal charges found on the structures that you write. REMEMBER: You ma not use an materials exce t those that are iven in the e uation. 7. (6, 3 each) The Williamson ether synthesis is important for introducing simple ethers to pharmaceuticals and other organic molecules. In each box provided, draw the product of the reaction. Note that the product also must be the correct starting material for the subsequent step. E:j/OH NaH j—...—.—..—.—>. THF socg CchHQCHz-OH Fwfidme Hour Exam II (a), Chemistry 301, Spring 2008, Page 5 of6 pages ...
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