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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2. Histamine (below structure) is a signal molecule involved in immune response and is a neurotransmitter. Histamine features imidazole ring which is an aromatic heterocycle. Please answer the following questions regarding Histamine. b a HN =N C NH2 a. Determine hybridization of each N atom (s, p, sp, sp², sp³, etc.) in histamine N-a hybridization: N-b hybridization: N-c hybridization: b. Determine what atomic orbitals (s, p, sp, sp², sp³, etc.) of the lone pair of each N atom resided in N-a hybridization: N-b hybridization: N-c hybridization:
None
29. Use frontier orbital analysis (HOMO-LUMO interactions) to decide whether the following dimerization is 1) thermally allowed or forbidden and 2) photochemically allowed or forbidden. +

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