FORMATIVE ASSESSMENT: CARBOXYLIC ACIDS AND ESTERS
1. Fill in the missing name or structural formula in the chart below. For letters g-i, fill in both the structural
formula and the name of the compound.(2 points each)
CH3
H3C
O
O
OH
O
b.
CH3
a.
c. pentanoyl chloride
d. 3-methyl butanoic anhydride
e. (CH3)2CHCCCH2COOH
f. CH3COOCH2CH3
2. Arrange the compounds below in order of increasing boiling point:
a. pentane
b. butanol
c. propanol
d. butanoic acid
_____
< ______
< ______
< _____
e. butanone
< _____
3. Arrange the compounds below in order of solubility in water:
a. pentane
_____
b. butanol
< ______
c. propanol
< ______
4. Draw the structure for aluminum propanoate.
< _____
d. butanoic acid
< _____
e. butanone
5. Reaction Practice: Draw the structural diagram for each reaction below:
a. benzoic acid + sodium hydroxide
H+
b.
acetic acid + isopropanol
H+
c.
ethyl methanoate + water
d.
methyl butanoate + lithium hydroxide
e. glycerol + 3 butanoic acid molecules 
f.
2 propanoic acid 
(propanoic acid + propanoic acid)
g.
butanoyl bromide + 1-hexanol
6. Determine the reactants and conditions necessary to produce:
O
O
CH3
a.
+
H3C
OH
H2O
+
H3C
OH
b.
O
7. Use the steps below to write out the reaction mechanism for acetic acid and 2-propanol
1. The carboxyl oxygen of the carboxylic acid is protonated.
2. An alcohol molecule adds to the carbocation produced in Step 1.
3. A proton is lost from the oxonium ion generated in Step 2.
4. A proton is picked up from solution by a hydroxyl group.
5. A pair of unshared electrons from the remaining hydroxyl group helps the water molecule leave.
6. The oxonium ion loses a proton to generate the ester.