The carbonyl group can be reduced by addition of a hydride ion (H⁻) and (H⁺) a proton 
. Removal of H⁻ and H⁺ from an alcohol results in a carbonyl group   <IMAGE>


b. In the reaction, indicate which direction represents reduction and which represents oxidation.

Draw the condensed structural formula for the alcohol formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:

c. 3-chlorocyclopentanone

Determine the alcohol product formed in the following reaction.

Determine which reactant should be used to produce the following alcohol.

The carbonyl group can be reduced by addition of a hydride ion (H⁻) and (H⁺) a proton 

. Removal of H⁻ and H⁺ from an alcohol results in a carbonyl group   <IMAGE>

a.To which atom of the carbonyl is the hydride ion added and why?

Write the structures of the hemiacetal or hemiketal that result from reactions (a) and (b). Write the structures of the complete hydrolysis products of the acetal or ketal in (c) and (d).

Acetone + Ethanol → ?

What ketones or aldehydes might be reduced to yield the following alcohols?

a. <IMAGE>

b. <IMAGE>

c. HOCH₂―CH₂―CH₂OH

Draw the structures of the products formed when the following compounds react with a reducing agent.

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Can the alcohol (CH₃)₃COH be formed by the reduction of an aldehyde or ketone? Why or why not?