Download Key Practice Exam 3

Practice Exam 3 (100 Points)
Disclaimer: this practice exam is not a mirror image of the actual test nor does it contain
all the material you will be tested on (please see the exam study guide on testable
material). The aim here is to help you become familiar with test format and the type of
questions you will be asked.
1. Name the following compounds
O
O
Br
HO
O
Isopropyl butyrate
(1-methylethyl butanoate)
4-bromobutanoic acid
O
O
OH
O
2,4-dimethylbenzoic acids
Cyclobutyl propionate
2. Draw the structure of the following compounds
a. 3-methylpentanoic acid
O
OH
b. Methyl-3-cyclohexylpropanoate
O
O
3. Identify the following as a hemiacetal or acetal
hemiacetal
acetal
hemiacetal
4. Rank in increasing order the boiling points trends you would expect for alcohols,
alkanes, ketones and carboxylic acids. Provide rationale for your ranking.
Carboxylic acid > alcohol > ketones > alkanes
The ranking is based on the ability of these compounds to form hydrogen bonds (their
attractive intermolecular forces). Carboxylic acids can form two hydrogen bonds (they
are dimmers), followed by the monomeric hydrogen bonding between alcohols. Ketones
can’t hydrogen bond but have electronegative oxygen and alkanes lack intermolecular
forces.
5. Provide synthetic route for the following organic compounds, starting with the started
material and show all intermediate steps
a. 3-methylpentanoic acids starting with an alcohol and show all intermediate
reactions.
O
O
[O]
[O]
OH
OH
H
3-methylpentanoic acid
b. Butyl acetate from appropriate alcohol and acid
O
OH
1-butanol
+
HO
acetic acid
O
O
butyl acetate
6. Succinic acid is an intermediate in the citric acid cycle. The structure of succinic acid
is shown below. Provide two compounds that you could oxidize to form succinic acid
and show their reaction
O
OH
HO
O
1. Starting with an aldehyde
O
O
H
Excess
H
[O]
OH
HO
O
O
2. Starting with an alcohol
O
O
Excess
Excess
OH
H
OH
HO
[O]
H
HO
[O]
O
O
7. Predict the product(s) that forms in the following reactions
O
O
+ NaOH
O
+
O Na
OH
HO
O
+
+
+ H
H
2O
+ H3O+
O
O
O
H2N
O
+ NaOH
O
H2N
Na+
HO
O