Ch 20 answers - 1 Answers to Ch. 20 Extra problems Chem....

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1 Answers to Ch. 20 Extra problems Chem. 345, SFN 1. Show the major product (or products if more than one will be formed in significant amount) for the following reactions: a. b. c. d. e. f. Put in order of basicity (1 = most basic, 4 = least basic). (CH 3 ) 2 NH (CH 3 ) 2 NK (CH 3 ) 4 NBr (CH 3 ) 2 N-N=O ___2___ ___1___ ___4___ ___3___ typical about as Br is a very NO is strong EWG dialkylamine LDA poor base! so is a feeble base NO 2 O H 2 , Pd/C But these are reductive amination conditions and if continue hydrogenating would obtain: NH 2 O OH H 3 C -H 2 O N H 3 C H 2 NH 2 O N H NH H 3 C H (made by conjuagate addition of Me 2 C( - )NO 2 to H 2 C=CHC(=O)Me) first reduces to the amine (H 3 C) 3 C I 1. NaNH 2 ,NH 3 (liq.) 2. neutralize (H 3 C) 3 C (through the benzyne) (H 3 C) 3 C NH 2 (H 3 C) 3 C NH 2 (oops, this is from Ch, 21, not 20, but is for Ex.3 H H 3 C N(CH 3 ) 2 H 1. H 2 O 2 2. heat H 3 C H Cope elimination (goes through 5- membered ring) N C O OH N H O O Br Br CH 3 1. NaNO 2 , H 2 SO 4 , cold 2. H 3 PO 2 , H 2 O NH 2 Br Br CH 3 H
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2 2. Show regents and any intermediate compounds that would be isolated for the following conversions. Any reagents stable enough to buy may be used. b.
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This note was uploaded on 02/14/2011 for the course ORGANIC CH 341 taught by Professor Idk during the Spring '11 term at University of Wisconsin.

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Ch 20 answers - 1 Answers to Ch. 20 Extra problems Chem....

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