Question

The hydroboration-oxidation of internal alkynes produces ketones. (a) When hydroboration-oxidation is applied to 2 -butyne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation. (b) When hydroboration-oxidation is applied to 2 -pentyne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.

          The hydroboration-oxidation of internal alkynes produces ketones.
(a) When hydroboration-oxidation is applied to 2 -butyne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation.
(b) When hydroboration-oxidation is applied to 2 -pentyne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.

Added by Cory Y.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

12/31/2021

Step 1

The intermediate formed after hydroboration is an alkylborane, which is then oxidized to form the ketone product. ** Show more…

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The hydroboration-oxidation of internal alkynes produces ketones. (a) When hydroboration-oxidation is applied to 2 -butyne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation. (b) When hydroboration-oxidation is applied to 2 -pentyne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.