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HW8-KEY - Sessler CH310M/318M H omework Problem Set 2...

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Sessler CH310M/318M Homework Problem Set 2 Due Friday April 8, 2011 1 Circle the section in which you are enrolled: 310M 318M Please write the first three letters of your last name in the above boxes Name:_______________________________ UT EID:_____________________________ Signature:____________________________ Grade ( + / - / 0 ):______________________
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Sessler CH310M/318M Homework Problem Set 2 Due Friday April 8, 2011 2 1. Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. CH 3 O - Na + Methanol Cl NaI Acetone Cl (CH 3 ) 3 CO - K + I NaI OTs Ethanol heat I MeCN MeOH Mechanism E2 I SN2 E2 I SN1 E1
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Sessler CH310M/318M Homework Problem Set 2 Due Friday April 8, 2011 3 2. Treatment of 4-chloro-1-butanol with one equivalent of lithium diisopropylamide (LDA) as a base leads to rapid formation of a compound with the molecular formula C 4 H 8 O. Propose a structure and a complete arrow pushing mechanism for its formation. O Cl LDA DMF H N Li + O Cl Li + O
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Sessler CH310M/318M Homework Problem Set 2 Due Friday April 8, 2011 4 3. For the reaction of (R)–1-phenylpropan-2-yl-4-methylbenzenefulfonate
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