Midterm_2_partB_V2_KEY

Midterm_2_partB_V2_KEY - Chem140C Spring 2008 Midterm 2...

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Chem140C – Spring, 2008 Midterm 2, Part B, Version 2, KEY 1. (15 points) For each pair of amines, write in the box which is more basic, A or B: A B N N CH 3 H H H N NH 2 NH 2 N CH 3 A A B 2. Circle the most likely product. (a) (TWO products) (10 points) O OH HO HO HO OH MeOH HCl (cat.) CHO OH HO HO OH OH H H H H O OMe MeO MeO OMe OMe O OMe MeO MeO OMe Br O OH HO HO HO O O HO OH OH HO O OH HO HO HO OMe O OH HO HO HO OMe (b) (5 points) O Cl 2 O Cl O O Cl Cl Cl Cl Cl Cl O Cl O O Cl Cl
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Chem140C – Spring, 2008 Midterm 2, Part B, Version 2, KEY Page 2 of 4 3. (30 points) Write a detailed, arrow-pushing mechanism consistent with the formation of 2 as the exclusive product of the reaction. O OMe OMe O NaCN + CN CO 2 Me OH 1 2 1) MeOH solvent 2) acidic workup O OMe OMe O N C O OMe C NC OMe O CN OMe O CO 2 Me CN OMe OH CO 2 Me H CN CO 2 Me O H also OK (but not quite as good) to protonate to get this: and then pull the proton with a base to eliminate methoxide (E2 elimination) MeO CN CO 2 Me O MeO–H CN CO 2 Me OH keto-enol tautomerization – MeO
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