Show how you would synthesize the following compounds from alkyl halides, vinylhalides, and aryl halides containing no more than six carbon atoms.  trans-oct-3-ene

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.60P: 17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the...
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Show how you would synthesize the following compounds from alkyl halides, vinyl
halides, and aryl halides containing no more than six carbon atoms.
  trans-oct-3-ene

Expert Solution
Step 1

A Corey-House alkene synthesis reaction is the reaction of the alkene. In this reaction lithium diorganyl cuprate (R2CuLi) with an organyl (pseudo)halide (R'X). Vinyl lithium compound is used to form an alkene. Copper iodide is used as the catalyst.  Vinyl part of reactant generally attached to form vinyl lithium cuprate.

Step 2

Reaction:

To synthesize trans-oct-3-ene (E isomer resembles trans-isomer), Reaction used is called Corey-House alkene synthesis reaction. (E)-pent-2-en-1-yllithium is used to react with copper iodide, to form dialkyl lithium cuprate. This reaction is followed by the addition of 1-bromopropane. This will give trans-oct-3-ene. Chemistry homework question answer, step 2, image 1

 

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