Princeton 2012/Barron 4th ed.
AP Practice Problems
Unit 16 – Organic Chemistry
Essays
1. CH3CH2COOH + CH3CH2OH  CH3CH2COOCH2CH3 + H2O
The organic acid combines with an alcohol to form an ester and water, as shown above.
a. Draw the structural formulas for the following:
i.
The organic acid
ii.
The alcohol
iii.
The ester
b. For the organic acid that you drew in part (a.i.)
i.
State the hybridization of the carbon atom in the O-C-O bond.
ii.
Predict the bond angle in the O-C-O bond.
iii.
Indicate the number of pi and sigma bonds in the molecule.
c. Explain why methanol and methanoic acid are soluble in water, while methane is not.
d. Dibromoethene, C2H2Br2, exists in three isomers. Draw two of them.
2. Use the information in the table below to answer the following questions.
Compound Name
Butane
1-butyne
1-chlorobutane
2-butanone
1-butanol
Pentane
Compound Formula
CH3CH2CH2CH3
CH3CHCHCH3
CH3CH2CH2CH2Cl
CH3COCH2CH3
CH3CH2CH2CH2OH
CH3CH2CH2CH2CH3
a. Draw the structural formulas for the following:
i. 1-chlorobutane
ii. 2-butanone
Boiling Point (K)
273
281
352
353
391
309
Princeton 2012/Barron 4th ed.
b. For each pair of compounds below, explain the differences in boiling point.
(Include specific information about each compound in your answers.)
i. Butane and Pentane
ii. Butane and 2-butanone
iii. 1-chlorobutane and 1-butanol
c. Each of the compounds below exists in two different forms. Darw the structural
formula for both isomers of each compound.
i. Butane
ii. Butyne
d. A researcher is trying to separate a solution of 1-chlorobutane and 2-butanone.
Why would distillation be a poor choice?
Princeton 2012/Barron 4th ed.
Answer Key – Organic Chemistry
1. E
2. A
3. B
4. C
5. E
6. A
7. D
8. C
9. D
10. A
11. C
12. E
13. A
14. A
15. D