CLG 12 – Delocalized Electrons II (10/18/21) 1. 2,3-dimethyl-1,3-pentadiene can conceivably give four products when reacted with HCI, however, only two products predominate. Write a mechanism for this reaction that shows the two products and how they are formed. Which product is favored under kinetically controlled conditions and which is favored under thermodynamically controlled conditions? Explain. 2. Write structural formulas for the major organic product(s) for the following reactions. Be sure to carefully indicate the stereochemistry when relevant. (а) (b) CH,=CH-CH=CH, CH,=CH-CEN heat (c) + H,C=CH-c-H

CLG 12 – Delocalized Electrons II (10/18/21) 1. 2,3-dimethyl-1,3-pentadiene can conceivably give four products when reacted with HCI, however, only two products predominate. Write a mechanism for this reaction that shows the two products and how they are formed. Which product is favored under kinetically controlled conditions and which is favored under thermodynamically controlled conditions? Explain. 2. Write structural formulas for the major organic product(s) for the following reactions. Be sure to carefully indicate the stereochemistry when relevant. (а) (b) CH,=CH-CH=CH, CH,=CH-CEN heat (c) + H,C=CH-c-H

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.
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