1) Draw the structure of the following named compounds. (4 points)
2) Classify the following structures as aromatic (A), anti-aromatic (AA) or non-aromatic
(NA). Assume all structures are planar (i.e. all atoms lie in the same plane). (5 points)
3) Answer questions a) and b) below with respect to the molecules shown. (2 points)
a) Which compound has a greater energy gap between its HOMO and LUMO? ___B___
b) Which compound has a longer max in its UV-Vis absorbance spectrum? ___A___
4) Answer questions a) and b) below with respect to the molecule shown. (2 points)
a) Which carbon-oxygen bond is the shortest? ___e____
b) Which carbon-oxygen bond is the longest? ____d____
– 1–
, 5) Answer questions a) and b) below with respect to the molecule shown. (2 points)
a) How many atoms are part of the molecule’s conjugated
system?
____12____
b) How many electron pairs are part of the molecule’s
conjugated system?
____7____
6) Circle the most likely mechanism for the following reactions. (3 points)
7) Consider the bromination reaction of 2-methylfuran shown here:
Indicate whether the structures below are acceptable resonance contributors for the
intermediate in the above reaction. (4 points)
8) Fill in the missing reagents and/or structures for each of the following transformations.
Where more than one product can form, show only the major product. (18 points, 2 points
per box).
– 2–
2) Classify the following structures as aromatic (A), anti-aromatic (AA) or non-aromatic
(NA). Assume all structures are planar (i.e. all atoms lie in the same plane). (5 points)
3) Answer questions a) and b) below with respect to the molecules shown. (2 points)
a) Which compound has a greater energy gap between its HOMO and LUMO? ___B___
b) Which compound has a longer max in its UV-Vis absorbance spectrum? ___A___
4) Answer questions a) and b) below with respect to the molecule shown. (2 points)
a) Which carbon-oxygen bond is the shortest? ___e____
b) Which carbon-oxygen bond is the longest? ____d____
– 1–
, 5) Answer questions a) and b) below with respect to the molecule shown. (2 points)
a) How many atoms are part of the molecule’s conjugated
system?
____12____
b) How many electron pairs are part of the molecule’s
conjugated system?
____7____
6) Circle the most likely mechanism for the following reactions. (3 points)
7) Consider the bromination reaction of 2-methylfuran shown here:
Indicate whether the structures below are acceptable resonance contributors for the
intermediate in the above reaction. (4 points)
8) Fill in the missing reagents and/or structures for each of the following transformations.
Where more than one product can form, show only the major product. (18 points, 2 points
per box).
– 2–
