Exam 2 -- Fall 2006 -- ANSWERS _do not distribute_

Exam 2 -- Fall 2006 -- ANSWERS _do not distribute_ - Name _...

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Name _______________________ Page 1 F.06.215E2 I. (24 points) The reaction rate for the following transformation was studied for a series of molecules that differed according to the identity of the group (labelled " Z ") on the phenyl ring ( JOC 2006 71 , 7650). O O O O Z H NaOCH 3 CH 3 OH O O O O Z Na + Z = H, Compound A Z = Cl, Compound B Z = CH 3 , Compound C (a) The pKa values for the three Compounds are 3.10, 3.00, and 2.70; which corresponds to which? i) Which compound corresponds to the pKa of 3.10? ii) Which compound corresponds to the pKa of 3.00? iii) Which compound corresponds to the pKa of 2.70? (b) Quantitatively, how many times more acidic is the most acidic of these three compounds relative to the least acidic one? (c) The rates of these three intramolecular acylation reactions were measured, and the relative rates were observed to be 1:20:80 (that is, one of them was 20x faster than the slowest one, and the other was 80x faster than the slowest one). i) Which compound was fastest? ii) Which compound was slowest? (d) Provide the complete, step-wise mechanism for the reaction of Compound A that results in the observed products. C A B 10 0.40 B C O O O O H OCH 3 O O O O O O O O O O O O Na deprot mech = 2 carboylate = 3 addition = 2 tet intermediate = 3 elimination = 2 12 2 2 2 2 2 2 -5 for not deprotonating first. .. remember: acids are acids!
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Name _______________________ Page 2 F.06.215E2 II. (15 points) Complete the following transformations as indicated by the data provided. Sequential experimental
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This note was uploaded on 09/21/2011 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.

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Exam 2 -- Fall 2006 -- ANSWERS _do not distribute_ - Name _...

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