Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 15, Problem 15.8P

Show how to convert 1-bromopentane to each of these compounds using a lithium diorganocopper (Gilman) reagent. Write an equation, showing structural formulas, for each synthesis.

  1. (a) Nonane
  2. (b) 3-Methyloctane
  3. (c) 2,2-Dimethylheptane
  4. (d) 1-Heptene
  5. (e) 1-Octene
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Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentane
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