CHEMISTRY 122
MIDTERM#2
CHAPTERS 6, 8, 9, 10 & 11
JUNE 10, 2015
1. Using the formula C5H8Br2 draw structures for the following:
a. A pair of constitutional isomers
b. A pair of enantiomers
c. A pair of geometric isomers (cis/trans) that are achiral
d. A pair of geometric isomers that are chiral.
e. A meso compound.
2. What structural feature causes an amine to be basic?
Nonbonding electrons found on the nitrogen.
3. Draw and name the four constitutional isomers of C3H9N.
4. Circle the statements that are true.
a. Hydrogen bonding between 2° amine is stronger than that between 2° alcohols.
b. Primary and secondary amines generally have higher boiling points than hydrocarbons with
comparable carbon skeletons.
c. The boiling points of amines increases as the molecular weight of the amine increases.
d. The VSEPPR model predicts bond angles of 120° about the carbonyl carbon of aldehydes and
ketones.
e. The product of a carboxylic acid and a strong base produces salt and water/
f. The carbonyl carbon of a carboxylic acid can be a stereocenter, depending on its location within
a molecule.
g. Carboxylic acids have lower boiling points when compared to alcohols of similar molecular
weight.
h. Epimers are diastereomers
i. Enantiomers contain a plane of symmetry
5. Label the following as hemiacetals, acetals, or neither hemiacetals or acetals.
6. Give acceptable names for the following.
7. Give the major products for the following.
8. Give a stepwise mechanism for the following transformation.
9. From each pair of compounds, circle the stronger base.
10. Show how the following can be made from 1-propanol.