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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr
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Disiamylborane adds only once to alkynes by virtue of its

Chapter 21, Problem 22P

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QUESTION:

Problem 22P

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 not formed?

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QUESTION:

Problem 22P

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 not formed?

ANSWER:

Answer :

Step 1

(a) Draw the structural formulas of the reagents and the products in the preparation of disiamylborane.

To get the product disiamylborane first we have to react BH3 with 2-methyl-2-butene to give intermediate products and finally giving  disiamylborane.

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