CARBOXYLIC ACIDS WORKSHEET KEY

1. Name the following:

a. methanoic acid b. ethanoic acid
c. propanoic acid d. butanoic acid
e. 3-bromobutanoic acid f. 2-methylbutanoic acid
g. 2-isopropylpentanoic acid h. 2,2,5-trimethylhexanoic acid
i. 2-phenylpropanoic acid j. 2,5-dimethylbenzoic acid
k. 3-chlorobenzoic acid l. 4-isoproplybenzoic acid
2. Draw condensed structural formulas for the following:
2-methylpropanoic acid 2,2,5-trimethylhexanoic acid

4,5-dimethyl-3-nitrooctanoic acid para-bromobenzoic acid

2,4,6-trinitrobenzoic acid 2-ethylpentanoic acid

3. Arrange the following compounds in order of increasing boiling point. (All of the
compounds have about the same molar mass.)

–1-pentanol
– hexane
– butanoic acid
– pentanal
The correct order is: hexane, pentanal, 1-pentanol, butanoic acid
4. Which member of each of the following pairs of compounds would you expect to
have a higher solubility in water?

a. 2-butanone OR propanoic acid

propanoic acid because it can form hydrogen bonds with water (between the hydrogens of
water and the oxygen in the hydroxyl group) . In addition the carboxylic group is the most polar
of the functional groups making carboxylic acids soluble in polar water (recall the thumb rule of
solubility- polar dissolves polar, non-polar dissolves non-polar). In 2-butanone the carbonyl
group though polar it is not as accessible to water as it is in the carboxylic group causing
ketones to be less soluble in water relative to carboxylic acids

b. hexanoic acid OR ethanoic acid

ethanoic acid. Because C-H bonds are nonpolar then the shorter chain carboxylic acids are
more soluble in a polar solvent