OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305865617
Author: Brown, Iverson, Anslyn, FOOTE
Publisher: Cengage Learning US
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Chapter 17.8, Problem DQ

Permethrin and Bifenthrin

Pyrethrin is a natural insecticide obtained from the powdered flower heads of several species of Chrysanthemum. The active substances in pyrethrum, principally pyrethrins I and II, are contact poisons for insects and cold-blooded vertebrates. Although powders made from Chrysanthemum extracts have found widespread use, the active substances in them are destroyed rapidly in the environment. In an effort to develop synthetic compounds as effective as the natural insecticides but with greater biostability, chemists prepared a series of esters related in structure. Among the synthetic pyrethrenoids now in common use in household and agricultural products are permethrin and bifenthrin.

Chapter 17.8, Problem DQ, Permethrin and Bifenthrin Pyrethrin is a natural insecticide obtained from the powdered flower heads

As discussed above, the natural products pyrethrins I and II (not shown) are destroyed rapidly in the environment. One of the key changes in the structures of permethrin and bifenthrin relative to the pyrethrins was the substitution of naturally occurring methyl groups on the alkene with electron withdrawing groups (EWGs) such as chlorine and trifluoromethyl. What reactions of the alkene would the change of methyl groups to EWGs retard?

  1. 1. Oxidation of the double bond.
  2. 2. Electrophilic addition reactions.
  3. 3. Nucleophilic addition reactions.
  4. 4. Both 1 and 2.
  5. 5. All of the above.
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Chapter 17 Solutions

OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition

Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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