2007 Midterm 2

2007 Midterm 2 - Name: page 1 Chemistry C3443 Fall 2007...

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Unformatted text preview: Name: page 1 Chemistry C3443 Fall 2007 Midterm #2 75 minutes October 24, 2007 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 8 pages (including this face page). The total number of points is 100. I. II. 1. 2. 3. 4. III. IV. TOTAL: / 100 Name: page 2 I. Shown below is the folate analog methotrexate. Circle five different functional groups on the molecule. Name the functional groups and indicate their pKas (in intervals of 5, i.e. 5, 10, 15, etc.) (10 minutes, 20 points total) G9NH3 N/ \ N fl rflamm H NH2 N N '6) Name: page 3 II. 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 SNI, SN2, E1, or E2. Remember to clearly indicate the regiochemistry and stereochemistry for each reaction. Choose 3 of the 4 problems. (20 minutes, 40 points total) 1. 9 69 l. MeO Na , MeOH ©/\sn ——> 2. M 2. tBugD 16? Me: tBuOH Et Pr 3. G) NHZ NH2 i) —' 9' 4. I NHzMe ——> Name: page 4 HI. Draw a detailed, arrow—pushing mechanism for the following reaction. (10 minutes, 20 points) 969 O Na OMC + Mel —'> + N31 DMF Name: page 5 IV. Cystine can be reduced to cysteine using tributylphosphine in aqueous THF. Propose a reasonable mechanism for the reduction, shown below. (10 minutes, 20 points) 5H2 Bu P- SH . 3 ' HOZC\/\S/S\/\CO H —__> 2 + Bu3P=O 3 2 H20:THF NHz HZN cozn Name: page 6 Name: page 7 ...
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2007 Midterm 2 - Name: page 1 Chemistry C3443 Fall 2007...

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