An inexperienced graduate student treated dec-5-ene with borane in THF, placed the flask in a refrigerator, and left for aparty. When he returned from the party, he discovered that the refrigerator was broken and that it had gotten quite warminside. Although all the THF had evaporated from the flask, he treated the residue with basic hydrogen peroxide. Tohis surprise, he recovered a fair yield of decan-1-ol. Use a mechanism to show how this reaction might have occurred.(Hint: The addition of BH3 is reversible.)

An inexperienced graduate student treated dec-5-ene with borane in THF, placed the flask in a refrigerator, and left for aparty. When he returned from the party, he discovered that the refrigerator was broken and that it had gotten quite warminside. Although all the THF had evaporated from the flask, he treated the residue with basic hydrogen peroxide. Tohis surprise, he recovered a fair yield of decan-1-ol. Use a mechanism to show how this reaction might have occurred.(Hint: The addition of BH3 is reversible.)

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...

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Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.
Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.
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