1aa3-2010-tut6 - sodium acetate in acetic acid by an S N 1...

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CHEMISTRY 1AA3 February 22-26, 2010 TUTORIAL PROBLEM SET 6 ________________________________________________________________________ Chemistry 1AA3 1. Identify the nucleophile in the following reactions. 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? 3. Draw the mechanism for the reaction of sodium hydroxide and benzyl bromide. 4. Propose a synthesis of cyclopentanone from cyclopentene. 5. Stinker. Propose the synthesis of the methyl ester of acetyl salicylic acid (shown below) from salicyclic acid. 6. Describe how you could determine, by experiment, whether 2-bromopropane reacts with
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Unformatted text preview: sodium acetate in acetic acid by an S N 1 or S N 2 mechanism. 7. What is chemical biology? 8. Old Exam Question. What statement about pyrimidine (left) and/or pyrrole (right) is FALSE ? CHEMISTRY 1AA3 February 22-26, 2010 TUTORIAL PROBLEM SET 6 ________________________________________________________________________ Chemistry 1AA3 (A) Both compounds are aromatic. (B) All nitrogen atoms are sp 2 hybridized. (C) Pyrrole is a stronger base. (D) In pyrimidine, the orbitals containing the lone pairs of electrons are perpendicular to the -system. (E) The ion that results when pyrimidine is treated with HCl is aromatic....
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1aa3-2010-tut6 - sodium acetate in acetic acid by an S N 1...

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