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e2 - Name Page 1 F.06.215E2 I(24 points The reaction rate...

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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.
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