Chem 215H
Quiz 3B
1/27/06
Name: _____________________________
Lab: 220___ 221___ 230___ 231___
250___ 251___ 270___ 271___
1.) Draw a picture of the LUMO of Molecule A (a -type orbital).
Label all the nodes and indicate the signs of the orbitals with + and -.
Molecule A
Is this orbital typically considered
nucleophilic or electrophilic?
electrophilic
2
1
2.) Dr. Hicks has forgotten to label two amines that she may need for the Honors Cup proposal
projects. It is your job to help her characterize her starting material. (3 pts)
NH2
B
Which of the two amines will have a UV-Vis absorption at
the highest ? Why?
NH2
C- because the d-bond lowers E, increases 
C
Match the amine with it’s mass spec and fill in the information about its NMR spectra. (1 pt ea.)
Letter of
Amine
C
Number of
unique 1H
NMR peaks
5
1H NMR
peak integral
ratios
1:1:1:2:2
Number of
unique 13C
NMR peaks
3
Letter of
Amine
B
Number of
unique 1H
NMR peaks
3
1H NMR
integral
ratios
2:1:6
Number of
unique 13C
NMR
2
3.) Answer the following questions based upon the structures below and your knowledge of Diels Alder
chemistry (6 pts). Each question may have more than one answer.
A. Are these molecules dienes or dienophiles?
O
NC
CN
NC
CN
O
OCH3
________dienophiles__________________
O
O
W
X
Y
Z
B. Molecule X reacts with cyclopentadiene slower
than
W, Y
C. Which molecule reacts the fastest?
D. Draw the product of cyclopentadiene with molecule Z.
E. Circle the C with the least - e- density on molecule X.
W