This lab is about reduction reaction. Using sodium borohydride to reduct 4- tert

Question

This lab is about reduction reaction. Using sodium borohydride to reduct 4-tert-butylcyclohexanone to alcohol product which contains cis- and trans- 4-tert-butylcyclohexanols.

1. Identify a method you could use if it was necessary to isolate samples of each of the diastereomeric products.

2. Explain why it is necessary to add an aqueous solution of sulfuric acid to the reaction solution after the reduction to form the alcohol product.

3. One of the objectives of this experiment is to determine the diastereoselectivity of the reduction of a pro-chiral ketone with a small, achiral reducing agent. Compare your ratio of cis- and trans- products against those reported in the literature (See Chem. Educator article posted on Lab Archives). Are your results consistent with those previously reported in the literature? Explain any discrepancies and hypothesize on possible causes.

Explanation / Answer

1. The reduction of 4- tert- butyl cyclohexanone by sodium borohydride would produce two diastereoisomers. The diastereoisomers can be separated by column chromatograohy.

2. The treatment of the molecule with sodium boro hydride will reduce the keto group and sodium alcoholate is generated. To protonate the alcoholate addition of sulfuric acid is necessary that will produce the alcohol.

3. Trans isomer will be major as it is free of 1;3- diaxial interaction.

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