E3,241b,S05 - EXAM 3 CHEMISTRY 241b Dr Spurgeon ANSWER KEY...

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EXAM 3 CHEMISTRY 241b April 12, 2005 Dr. Spurgeon ANSWER KEY Each person’s score will be multiplied by 1.163 to accommodate the loss of problem 5. __________________________________________________________________________________________ 1. (20 points) Predict the product of the following reactions and provide the name of the reaction: a. b. c. d. OCH 3 O CH 3 O 2 NAME CH 3 O CH 3 CH 2 O OCH 3 O CH 3 O O O CH 2 COOCH 3 CH 2 C CH 3 O CH 3 O and OEt O O Claisen O O O OCH 3 Claisen Claisen Aldol Michael O O O O
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2. (10 points) The spicy flavor of cayenne pepper is due mainly to a a substance called capsaicin . The following sequence of steps was used in a synthesis of capsaicin . Deduce the structure of capsaicin on the basis of this synthesis. Remember – show all of your work. 3. (9 points) Complete the following condensation reactions: a. Diethyl malonate + 1-bromo-2-methylbutane b. Diethyl malonate + 6-methyl-2-cyclohexenone c. Ethyl acetoacetate + 1,4-dibromobutane OH PBr 3 C 8 H 15 Br H 3 CO OCH 3 O O then H 3 O + C 11 H 18 O 4 heat C 10 H 18 O 2 SOCl 2 C 10 H 17 ClO CH 2 NH 2 HO H 3 CO C 18 H 27 NO 3 Capsaicin NaOEt NaOEt
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