A student decided to alter the amounts of starting material employed in the hydr

Question

A student decided to alter the amounts of starting material employed in the hydroboration-oxidation of 1-octene in order to improve her yield of 1-octanol. She used 1.57 mL of 1-octene, 3 mL of the borane-THF solution, and 0.9 mL of 30% hydrogen peroxide in her procedure. Appropriately larger amounts of solvent and sodium hydroxide were also used. What was the theoretical yield of 1-octanol under these conditions? Nancy was surprised to find that her gas chromatogram of the product mixture contained more residual 1-octene and more trialkyl borane than was observed by the other students in her section. Explain.

Explanation / Answer

A student decided to alter the amounts of starting material employed in the hydr

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