201 - CH 2 Br 1) NaNH 2 2) CH 3 CH 2 Br H 2 /Lindlar cat....

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Practice Problem 2-1 Answer In each part below, one or more carbon-carbon bonds must be formed during the course of a multistep synthesis. Propose a sequence of reactions to prepare the indicated target compound from starting materials given. All carbon atoms in the target must originate in the designated starting materials. Given that restriction, you may use any other reagents necessary to complete the synthesis. C C H H 1) NaNH 2 2) CH 3
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Unformatted text preview: CH 2 Br 1) NaNH 2 2) CH 3 CH 2 Br H 2 /Lindlar cat. 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 OH (racemic) C C H H 1) NaNH 2 2) CH 3 (CH 2 ) 6 Br H 2 /Lindlar cat. 1) BH 3 2) H 2 O 2 , NaOH, H 2 O OH H 2 CrO 4 OH O 1) NaNH 2 2) CH 3 CH 2 Br H 2 /Lindlar cat. 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 OH (racemic) H 2 CrO 4 O C C H H 1) NaNH 2 2) CH 3 CH 2 CH 2 Cl 1) NaNH 2 H 2 /Lindlar cat. OH OH 2) CH 3 CH 2 CH 2 Cl 1) OsO 4 2) NaHSO 3 ( meso )...
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas at Austin.

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201 - CH 2 Br 1) NaNH 2 2) CH 3 CH 2 Br H 2 /Lindlar cat....

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