compound 3,4-dimethyl-hexan-3-ol of 3R, 4S configuration is treated with a concentrated HBr solution at room temperature. A mixture of two stereoisomers is obtained. If the reaction mixture above is heated, the appearance of several other compounds is observed. 1) Draw the different compounds obtained using the wedge-flywheel representation. 2) What is the majority product? Explain 3) Propose a modification of the experimental conditions in order to obtain the exclusive formation of these compounds obtained after heating

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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section20.6: Sigmatropic Shifts
Problem 20.12P
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The compound 3,4-dimethyl-hexan-3-ol of 3R, 4S configuration is treated with a concentrated HBr solution at room temperature. A mixture of two stereoisomers is obtained.
If the reaction mixture above is heated, the appearance of several other compounds is observed.

1) Draw the different compounds obtained using the wedge-flywheel representation.

2) What is the majority product? Explain

3) Propose a modification of the experimental conditions in order to obtain the exclusive formation of these compounds obtained after heating

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The organic compounds are interconverted to each other with the help of reagents. Some intermediates are formed in these reactions. One of them is carbocation. The carbocation is planar. The attacking reagent can attack via both above and below planes of a carbocation.

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