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Unformatted text preview: 1 Answers to Extra Problems for Ch. 17 1. Show the major product (or products if more than one will be formed in significant amount) for the following reactions. EtONa, EtOH, Heat H 3 C H O O a. aldol-dehydration aldehyde is a much better aldol acceptor than is a ketone acronym for reagent: ___LDA_____ CH 3 O 1. [(CH 3 ) 2 CH] 2 NLi THF, -78 o C 2. allylation of an ester enolate H 2 C=CHCN (2 eq.) NaOEt, EtOH name of reagent: acrylonitrile 1. [(CH 3 ) 2 CHCH 2 ] 2 AlH CH 3 H 3 C Br 1 eq., -78 o C 2. neutralize, H 3 O + acronym for reagent: __DIBAL-H__ OEt O 1. LDA, -78 o C 2. Benzyl bromide OEt O b. c. d. e. O O CN NC O O O O H O OH O O see 6-ring closure; it is much faster than 8 a double Michael O HO H kinetic deprotonation and alkylation 2 2. Show the major product (or products if more than one will be formed in significant amount) for the following reactions. CH 3 O 1. NaOH, H 2 O excess I 2 , heat 2. neutralize, H 3 O + iodoform (haloform) reaction 1. LDA, THF, -78 o C OH O 3. H 2 O 2 , warm 2. PhSeBr a selenoxide (B) elimination, through CO 2 Et a. b. 1. NaOEt 2. CH 3 I CO 2 Et 3. NaOEt, methylvinylketone heat enolate alkylation followed by a O O Robinson Annulation c. Claisen-Schmidt (would dehydrate under harsher conditions) CH 3 d. O O HOAc, Br 2 , 1 eq. major product in acid arises from the equilibrium, most substituted, enol MeOH, MeONa, Br 2 , 1 eq. major product in base arises from the kinetic enolate; will also see di- and some tribromide because the product is more more acidic than the starting material e....
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- Spring '11