Answers for Student Exercise 2.1 2.

9

1
N
a. benzonitrile
H
2
N
b. isobutylamine
S
O
O
c. diphenyl sulfone
O
O
d. dioxane
N
+
O
O
-
e. 1-nitropropane
O
HO
f. formic acid g. biphenyl
O
HO
h. benzoic acid
O
H
2
N
i. benzamide

O
O
Butyl acetate
O
NH
2
Butyramide
H
2
N
Isobutylamine
C
11
H
23
O
HO
Lauric acid
Na
+
O
O
-
Sodium propionate
Spectrum E Spectrum H Spectrum I Spectrum F Spectrum G

O
Allyl phenyl ether
O
Benzaldehyde
H
HO
o-Cresol
O
HO
m-Toluic acid
Spectrum L Spectrum M Spectrum K Spectrum J

2.1. Since the indicated carbon of phenylacetonitrile is sp
3
hybridized, it is reasonable for this compound to
show CH stretching at less than 3000 cm
-1
(2960-2940 cm
-1
). Where as benzonitrile has only aromatic
CH stretching which is typically between 3100 - 3000 cm
-1
(page 87).






2.2.
2.3.

2.4.
2.5.








C
CH
2
N
phenylacetonitrile
C N
benzonitrile

1,3-Cyclohexadiene Diphenylacetylene 1-Octene 2-Pentene
Spectrum B Spectrum A Spectrum D Spectrum C

Answers for Student Exercise 2.1 2.9

2
H
2
N
Aniline
N
N
Azobenzene
N
HO
Benzophenone oxime
H
2
N
Benzylamine
NH
2
Cl
Dimethylamine
hydrochloride
Spectrum Q Spectrum O Spectrum P Spectrum N Spectrum R

O O
O O
H
enol

2.6.

2.7. Methyl isothiocyanate CH
3
N=C=S
2.8. This diketone exists primarily (~ 90%) in enol form (in CCl
4
)



Enols such as this display broad, shallow OH stretching bands (here from 3400-2500 cm
-1
). The
strong band at ~1600 cm
-1
is the enolic coupled C=COH band. (See pages 80, 94, and 98)











Answers for Student Exercise 2.1 2.9

3
O
4-Heptanone
OH
3-Heptanol
Br
4-Bromotoluene
Br
2-Bromopentane
O
2-Hexanone
O
OH
Propionic Acid
H
2
N
Butylamine
OH
Propargyl alcohol
N
+
O
O
-
1-Nitropropane
O
OH
2-Phenoxylethanol
O
Phenetole
O
O
Methyl Butyrate
HO
O
O
Methyl salicylate
O
HN
Caprolactam
N
N
2-methylpyrazine
N
+
O
-
O
Cl
1-Chloro-4-Nitrobenzene
O
HO Br
7-Bromo Heptanoic Acid
HO
5-Hexyn-1-ol
O
6-Methyl-5-hepten-2-one
O
HO
Hexanoic acid
Cl
Cl HO
2,6-Dichlorophenol
HO
2,6-Dimethylphenol
O
2-Cyclohexen-1-one
A B C D
E F G
H
I J K L
M N O P
Q R S
T U V W
H

2.9.