210 - Li Cl CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 2 CuLi Li...

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Practice Problem 2-10 Answer Show how to bring about each conversion using a Gilman reagent. Practice Problem 2-11 Answer Complete these reactions involving Gilman reagents. Practice Problem 2-12 Answer Show how to convert 1-bromopentane to each of these compounds using a Gilman reagent. Write an equation, showing structural formulas, for each synthesis. (a) Nonane (b) 3-Methyloctane (CH 3 CH 2 CH 2 CH 2 ) 2 CuLi [(CH 3 ) 2 CHCH 2 ] 2 CuLi Br CuLi 2 ether Br CuLi 2 ether
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(c) 2,2-Dimethylheptane (d) 1-Heptene (e) 1-Octene Practice Problem 2-13 Answer In Practice Problem 2-12, you used a series of Gilman reagents. Show how to prepare each Gilman reagent from an appropriate alkyl or vinylic halide. (a) (b) (c) (d) (e) Br 2 ether CuLi Br 2 ether CuLi Br 2 ether CuLi CuLi 2 CuCl ether Li 2 + LiCl 2 + LiCl 4 Li Cl 2 CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 CuLi 2 Li Cl CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 2 CuLi Li Cl CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 2 CuLi
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Unformatted text preview: Li Cl CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 2 CuLi Li Cl Practice Problem 2-14 Answer Show how to prepare each compound from the given starting compound through the use of a Gilman reagent. (a) 4-Methylcyclopentene from 4-bromocyclopentene (b) ( Z )-2-Undecene from ( Z )-1-bromopropene (c) 1-Butylcyclohexene from 1-iodocyclohexene (d) 1-Decene from 1-iodooctane (e) 1,8-Nonadiene from 1,5-dibromopentane Practice Problem 2-15 Answer Gilman reagents are versatile reagents for making new carbon-carbon bonds. Complete the following reaction that uses a Gilman reagent. Br (CH 3 ) 2 CuLi ether CH 3 Br [CH 3 (CH 2 ) 6 CH 2 ] 2 CuLi ether I [CH 3 CH 2 CH 2 CH 2 ] 2 CuLi ether I [H 2 C=CH 2 ] 2 CuLi ether 2 [H 2 C=CH 2 ] 2 CuLi ether Br Br O O C H 3 OH (racemic)...
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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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210 - Li Cl CuCl ether 2 + LiCl 2 + LiCl 4 Li 2 2 CuLi Li...

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