Sas-exam2practice - CHEM 239B Spring, 2006 Prof. Sasaki...

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Spring, 2006 EXAM #2 Name . Prof. Sasaki 150 points TOTAL Good Luck! Note: Only answers in the box will be graded. _______________________________________________________________________ 1. (35) Reaction of the tertiary amine, tropinone, with benzyl bromide gives not one but TWO quarternary ammonium salts, A and B . Compounds A and B are stereoisomers. N H H H H H H H H H H H 3 C O + CH 2 Br A + B Tropinone (C 8 H 13 NO) [C 15 H 20 NO] + Br - (a) Propose structures for A and B . (b) What kind of stereoisomers are A and B ? (c) Circle the most acidic hydrogen(s) in tropinone. (d) Compounds A and B are interconverted by base (like OH - ); that is, base treatment of either pure isomer leads to an equilibrium mixture of the two. A B OH - Suggest a reasonable mechanism for the equilibrium of A and B by base. ( Hint: Think "reversible Hoffman elimination"
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Sas-exam2practice - CHEM 239B Spring, 2006 Prof. Sasaki...

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