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Unformatted text preview: CHEMISTRY 1AA3 February 22-26, 2010 TUTORIAL PROBLEM SET 6 SOLUTIONS ________________________________________________________________________ Chemistry 1AA3 1. Identify the nucleophile in the following reactions. SOLUTION: (i) NaN 3 (ii) NaOH (iii) (CH 3 ) 2 NH (iv) PhSH 2. In question 1-(iii), the reaction gives roughly 50% yield when an equivalent number of moles of nucleophile and electrophile are combined. When an excess of the amine is added the reaction goes to completion. Explain why? SOLUTION: The reaction produces HBr, a strong acid, which will protonate dimethylamine. With the lone pair tied up the compound is no longer a good nucleophile. With excess dimethylamine around, there is plenty of amine available to mop up the acid and react with the electrophile. 3. Draw the mechanism for the reaction of sodium hydroxide and benzyl bromide. SOLUTION: 4. Propose a synthesis of cyclopentanone from cyclopentene. Propose a synthesis of cyclopentanone from cyclopentene....
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