3. A primary alkyl bromide of molecular formula C6H13Br was found to be optically active. Treatment of this alkyl bromide with potassium tert-butoxide in tert-butyl alcohol gave an elimination product of molecular formula C6H12 that was optically inactive. Draw structures for an alkyl bromide and the elimination product derived from it that are consistent with these data

3. A primary alkyl bromide of molecular formula C6H13Br was found to be optically active. Treatment of this alkyl bromide with potassium tert-butoxide in tert-butyl alcohol gave an elimination product of molecular formula C6H12 that was optically inactive. Draw structures for an alkyl bromide and the elimination product derived from it that are consistent with these data

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...

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Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.
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An organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.
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