CHE 232-1, Summer 2008
Dr. Harris
Name (please print)___________________________________
Student ID #______________________________________
Short Answer: (4 pts each)
1) What type of information is provided by ultraviolet/visible spectroscopy?
identifies different types of pi bonds and conjugation
2) What is the multiplicity of the labeled proton?
H2
C
H3C
multiplet of 9
H2
C
C
H2
OH
3) How many peaks would you see for 2-pentanone in a proton NMR spectrum?
4
4) 2-pentene is reacted with HBr and peroxide. Draw the product.
Br
5) How many products would you get for the monochloronation of 2,2’dimethylbutane?
3
Predict the Product. (4 pts. each)
6)
Br2
ROOR
Br
7)
Cl2
ROOR
Cl
Cl
Cl
Cl
Cl
8)
NBS
hv
Br
Br
Br
Br
9)
Br
Br2
CCl4
Br
10)
HBr
Br
Mechanism: (Show all steps) (15 pts.)
11)
Br
Br2
CCl4
Br
Br
+
Br
Br
Br
Br
Br
Spectroscopy: (15 pts. each)
12) Using the MS, IR and +1H NMR spectra determine the formula and structure of
the unknown compound.
Molecular ion peak at 150 and 152.
C5H11Br
Br
200
Shift(ppm)
3.398 triplet
1.86 multiplet of 9
1.44 multiplet of 9
1.32 multiplet of 12
0.93
triplet
13) Using the following data, give the formula and structure of a compound with C,
H and O.
- Molecular ion peak at 102.
- IR peak at 2850-3000 cm-1.
- protn NMR data has a doublet at 1.1 ppm. (12H) and a septet at 3.6 ppm.
(2H)
C6H14O
O
14) Give the structure and formula using the following spectra.
Molecular ion peak at 87.
C4H9NO
O
N
Shift(ppm)
2.077 2
2.98 1
Exam Score
1-5 _________ (/20)
6-10_________ (/20)
11 ________ (/15)
12 _________ (/15)
13 _________ (/15)
14 _________ (/15)
Total________ (/100)