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Organic Chemistry I Exam 2

Organic Chemistry I Exam 2 - NAME SS Introductory Organic...

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Unformatted text preview: NAME SS# Introductory Organic Chemistry 030.104 MIDTERM EXAM #2 April 10, 2003 == -— _ 43 Circle Your TA’s Name CasTaldo, Lycma Dunks, Jill Gunsior, Michelle Hill, Eric Kapur‘, Preeya Liu, Yonglin Shah, Meha Wea’rherwax, Anthony 1) Predict the major product(s) for each of the following reactions. You do not need to show minor products. (4 pts each) B r2 H20 HCl HBr / ROOR Med O"—I H—Br Cl 0H9 DME 2) Propose a plausible mechanism for the following transformation: (10 pts) EOTS H20 ‘ OH 3) Propose a plausible mechanism for the following reaction: (10 pts) Br O—fifi Et/S\ Ill/S/Et 4) Propose a plausible synthesis for each of the following reactions. NOTE — you do NOT have to show mechanisms or intermediates. Simply show a list of reagents that you would need to carry out each of these transformations. (10 pts each) H—CEC—H m UBr*-—*© 5) Propose a plausible synthesis for each of the following reactions. NOTE — you do NOT have to show mechanisms or intermediates. Simply show a list of reagents that you would need to carry out each of these transformations. (10 pts each) 0 OH £5 OR M OR If 0 Br 6) We have learned about addition reactions across conjugated diene systems. We saw that there were two types of additions that could take place. a) Draw the two products for the reaction below: (2 pts) (j HBr _—__> + 1,2 1,4 b) Which product is the kinetic product? (Circle your choice here) 1,2 1,4 (1 pt) c) Which product is the thermodynamic product? (Circle your choice) 1,2 1,4 (1 pt) (1) Which product is favored at low temperature? (Circle your choice) 1,2 1,4 (1 pt) e) Draw an energy diagram below showing the 1,2 addition and the 1,4 addition. Clearly label which product comes from the 1,2 addition and which product comes from the 1,4 addition. (3 pts) Extra credit (1 point) Draw an energy diagram showing why it takes so long for diamonds to turn back into graphite. Explain with ONLY ONE SENTENCE. Energy Diagram Explanation ...
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