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Midterm 2 Key - Name Z Eng WEA— page 1 Chemistry C3443...

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Unformatted text preview: / Name: Z Eng WEA— @# page 1 Chemistry C3443 Fall 2006 Midterm #2 . 75 minutes 5 October 23, 2006 Instructions: (1) For some questions, you have a choice of which problem(s) to answer. For these, cross out (X) answers you do not want counted. (2) Notice that for each question, we have suggested how much time you spend on that question and indicated how many points it is worth. We suggest that you first go through the entire exam and answer the questions that are easier for you and then go back to the questions that are harder for you. (3) Put your name at the top of each page. (4) Unless indicated otherwise, all structures should be skeletal (line) drawings. The exam contains 10 pages (including this face page). The total number of points is 100. I. 1. 2. II. 1. 2. III. IV. 1. 2. 3. 4. V. 1. 2. TOTAL: / 100 Name: Answer E Q?! page 2 I. For the reactions shown below, (1) indicate if the equilibrium lies to the left or the right and (2) state the overall AG° for the reaction. Choose 1 of the 2 problems. / (7.5 minutes, 15 points total) 1. . Name: Egnsggg k€¥ P3333 II. Circle the molecules below that are chiral. For all chiral centers, indicate if the stereochemistry is S or R. Choose 1 of the 2 problems. (7.5 minutes, 15 points total) Name: Angwe: k 3% page 4 HI. Draw a detailed, arrow (10 minutes, 20 points) -pushingl mechanism for the following reaction. Name: A! )3 ever k 2 ¥ page 5 IV. For each of the substitution or elimination reactions shown below, (1) fill in the box with the appropriate reagent, major product or starting material. If NO REACTION occurs, write “NR”. (2) Indicate if each reaction is SN], 8N2, E1, or E2. Remember to clearly indicate the re giochemistry and stereochemistry for each reaction. Choose 3 of the 4 problems. (15 minutes, 30 points total) 1. foluM 3 CH2 CL) 2. )1 CI Se AA MCOH A) K 3. 4. HINT: this reaction is a substitution reaction l Name: ADS W Q: ICQL¥ page 6 is V. Choose 1 of the 2 problems. (10 minutes, 20 points) / R group relative rate methyl 540 ethyl 125 isopropyl 27 tert-butyl 1 Wanted beniu/l/Fc Common Momma, Ear opc/v‘ml Smiumb‘q m [(4/me m {0 WQ, ‘ {“51“ fiJNOLUhZ Name: Angweo kg} page 7 IV. continued. 2. Interestingly, the reaction shown below gave only the two products shown (HINT: note the stereochemistry). Provide a step~by—step mechanism that is consistent with this product distribution. CH3C02H H3CH_ Ph Ph 5 CH3 0 O _ n HOAC - k HOTos HO—S PhH = HO _ CH3 '1 ...
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