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1aa3-2012-tut10-q - amine is added the reaction goes to...

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CHEMISTRY 1AA3 Week of March 19, 2012 TUTORIAL PROBLEM SET 10 ______________________________________________________________________________ Page 1 of 2 1. Fill in the missing reagents a. to f. for the following transformations. O OH O H OH O O a. b. c. d. e. f. 2. Complete the following oxidation reactions (if no reaction occurs, write N.R.):
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2 3. Identify the nucleophile in the following reactions. 4. In sub-question (iii) above, the reaction gives roughly 50% yield when an equivalent number of moles of nucleophile and electrophile are combined. When an excess of the
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Unformatted text preview: amine is added the reaction goes to completion. Explain why. 5. Draw the mechanism for the reaction of sodium hydroxide and benzyl bromide. 6. Propose a synthesis of cyclopentanone from cyclopentene. 7. Describe how you could determine, by experiment, whether 2-bromopropane reacts with sodium acetate in acetic acid by an S N 1 or S N 2 mechanism. I + NaN 3 N 3 + NaI Br NaOH OH + NaBr Br + H N N + HBr I + PhSH SPh + HI (i) (ii) (iii) (iv)...
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