Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?

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
Chapter7: Alkynes
Section: Chapter Questions
Problem 7.26P
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Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamyl
groups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.
(a) Draw the structural formulas of the reagents and the products in the preparation of
disiamylborane.
(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why is
Sia3B not formed?

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