Soluções cap 02 Silverstein

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Answers for Student Exercise 2.1 – 2.9 
 
1
N
a. benzonitrile
H2N
b. isobutylamine
S
O
O
c. diphenyl sulfone
O
O
d. dioxane
N+
O
O-
e. 1-nitropropane
OHO
f. formic acid g. biphenyl
O
HO
h. benzoic acid
O
H2N
i. benzamide 
O
O
Butyl acetate
O
NH2
Butyramide
H2N
Isobutylamine
C11H23
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 sp3 hybridized, it is reasonable for this compound to 
show C−H stretching at less than 3000 cm-1 (2960-2940 cm-1). Where as benzonitrile has only aromatic 
C−H stretching which is typically between 3100 - 3000 cm-1 (page 87). 
 
 
 
 
 
 
2.2. 
2.3. 
 
2.4. 
2.5. 
 
 
 
 
 
 
 
 
C
CH2
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
H2N
Aniline
N
N
Azobenzene
N
HO
Benzophenone oxime
H2N
Benzylamine
NH2 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 CH3−N=C=S 
2.8. This diketone exists primarily (~ 90%) in enol form (in CCl4) 
 
 
 
 Enols such as this display broad, shallow O−H stretching bands (here from 3400-2500 cm-1). The 
strong band at ~1600 cm-1 is the enolic coupled C=C−OH 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
H2N
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
ClHO
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.