13. Alcohols and Carbonyl Compounds

Show how you would make each compound, beginning with an alcohol of your choice.

(d)

(e)

(f)

Draw a mechanism for the following oxidation reactions.

(b)

What is the product of the reaction?

What is the product of the reaction?

What is the product of the reaction?

In Chapter 13, we explain how to convert secondary alcohols into ketones using a mild oxidation reaction. When the following enantiomerically pure and optically active secondary alcohol is submitted to these reaction conditions, the product is optically inactive. Explain this observation.

What is the major product(s) of each of the following reactions?

c.

What is the major product(s) of each of the following reactions?

h.

Two unknowns, X and Y, both having the molecular formula C₄H₈O, give the following results with four chemical tests. Propose structures for X and Y consistent with this information.

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the Lewis structures of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

a. the Cr in chromic acid

b. the Cl in sodium hypochlorite

c. the S in the Swern oxidation