15. Aldehydes and Ketones

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?

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.

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?

Indicate which compounds contain aldehyde or ketone carbonyl groups.

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Indicate which compounds contain aldehyde or ketone carbonyl groups. 

CH₃CH₂―O―CH₂―CHO 

Indicate which compounds contain aldehyde or ketone carbonyl groups.

<IMAGE>

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:

d. 2-methyl-3-pentanone

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:

a. ethyl propyl ketone

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:

a. butyraldehyde

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. hexanal

Draw the condensed structural or line-angle formula for the alcohol produced when hydrogen and a nickel catalyst reduce each of the following: (12.4)

b. <IMAGE>

Which compound in each of the following pairs would be more soluble in water? Explain.

c. butanal or hexanal

Draw the condensed structural or line-angle formula for the alcohol produced when hydrogen and a nickel catalyst reduce each of the following: (12.4)

b. <IMAGE>

Draw the condensed structural or line-angle formula for the alcohol produced when hydrogen and a nickel catalyst reduce each of the following: (12.4)

a. <IMAGE>

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