14. Compounds with Oxygen or Sulfur

Determine the product created under the following oxidation reaction.

Which of the following alcohols cannot undergo an oxidation reaction?

What products would you expect from oxidation of the following alcohols?

a. CH₃CH₂CH₂OH

b. <IMAGE>

c. <IMAGE>

From what alcohols might the following carbonyl-containing products have been made (red=O,reddish-brown=Br)?

(a) <IMAGE>

(b) <IMAGE> 

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.

a. <IMAGE>

b. <IMAGE>

c. <IMAGE>

What alcohols would you oxidize to obtain the following carbonyl compounds?

a. <IMAGE>

b. <IMAGE>

c. <IMAGE>

'Designer vinegars' have become very popular over the past decade. Vinegars made from champagne, merlot, and other wines are but a few of these. All wines contain ethanol, and these vinegars are simply wines containing microorganisms that have caused oxidation of the ethanol present. If vinegar is simply ethanol that has been oxidized, what is the structure of the acid formed?

Draw the structures of the aldehydes that might be oxidized to yield the following carboxylic acids:

CH₃CH=CHCOOH

A compound with the formula C₅H₁₀O oxidizes to give 3-pentanone. Draw the condensed structural formula and give the IUPAC name for the compound. (12.3, 12.4)

Write the balanced chemical equation for the complete combustion of each of the following compounds:

b. 3-hexanol

Draw the condensed structural or line-angle formula for the aldehyde or ketone formed when each of the following alcohols is oxidized [O] (if no reaction, write none):

d. <IMAGE>

Draw the condensed structural formulas for the aldehyde and carboxylic acid produced when each of the following is oxidized:

c. 3-chloro-1-propanol

Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions: (12.4)

c. <IMAGE>

A compound with the formula C₅H₁₀O oxidizes to give 3-pentanone. Draw the condensed structural formula and give the IUPAC name for the compound. (12.3, 12.4)

Are each of the following soluble, slightly soluble, or insoluble in water? Explain.

a. CH₃—CH₂—CH₂—OH