Answers and Solutions Manual for Student Exercises for Spectrometric Identification of Organic Compounds (8th Edition) by Robert M. Silverstein, Francis X. Webster, David J. Kiemle, and David L. Bryce – Complete Step-by-Step Spectroscopy Problem Solutions

All 8 Chapters Covered




PDF
Spectrometric
ldentification of
Organic Compounds

,
,Answers for Student Exercises 1 .1 to 1 .5 1

Atom Type # of Atoms Mass Total Mass
Hydrogen 22 1.00783 22.17226
a
Carbon 10 12.00000 120.00000
Nitrogen 0 14.0031 0.00000
3-ethyloctane Oxygen 0 15.9949 0.00000
C10H22 Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 0 Exact Mass 142.17226

- (C2Hs•) +


[ r Rule 3
..
[ r - (CH2=CH2) +
+



Rule 9

b Atom Type # of Atoms Mass Total Mass
Hydrogen 18 1.00783 18.14094
Carbon 10 12.00000 120.00000
Nitrogen 0 14.0031 0.00000
3-butylcyclohex-1-ene Oxygen 0 15.9949 0.00000
C10H18 Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 2 Exact Mass 138.14094




[
[
rr or



- (C4H9 )
•
Rule 5 and 6 .. 0

Rule 6
.-.
r r .. r
- (CH)=CH
- 7 )


[
r r - (C3H7•) \_)/ ..

, @SOLUTIONSSTUDY


+
• \ /
+
Rule 3

,Answers for Student Exercises 1 .1 to 1 .5 3

0 Atom Type # of Atoms Mass Total Mass
Hydrogen 18 1.00783 18.14094
Carbon 13 12.00000 156.00000
c
Nitrogen 0 14.0031 0.00000
2-methyl-1-phenylhexan- l-one Oxygen 1 15.9949 15.99490
C13H1sO Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 5 Exact Mass 190.13584




o+
Rule 8

+ +


Rule 9 \=I rH
. ---
\=I
H
/


- (CO)

O
+
I
Rule 8+9

Atom Type # of Atoms Mass Total Mass
d Hydrogen 22 1.00783 22.17226
Carbon 11 12.00000 132.00000
(E)-undec-3-ene
C11H22 Nitrogen 0 14.0031 0.00000
Oxygen 0 15.9949 0.00000
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 1 Exact Mass 154.17226




+
+



[ (;
.
•
3
..
r -Rule
(CH 5)


•
+




0
r. -(
C5H13)

Rule 5
.. +
+




- (C7H14) +
Rule 9

, @SOLUTIONSSTUDY
Atom Type # of Atoms Mass Total Mass
e Hydrogen 18 1.00783 18.14094
Carbon 12 12.00000 144.00000
Nitrogen 0 14.0031 0.00000
l-(hexan-2-yl)benzene Oxygen 0 15.9949 0.00000
C12 H18
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 4 Exact Mass 162.14094

.
+
+
•3
- (CH )
Rule 7 ..
.
+


- (C4H9 )

Rule 7
•
.. 0)
t

.
+ - (C4H3 )
Rule 9 .. [Cf]
Atom Type # of Atoms Mass Total Mass
Hydrogen 16 1.00783 16.12528
Carbon 7 12.00000 84.00000
Nitrogen 0 14.0031 0.00000
heptan-2-ol
Oxygen 1 15.9949 15.99490
C7H160
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1= 0 Exact Mass 116.12018

•
•+H
- (CsH11 )

Rule 8
.. + H


.. OH

H
- (CH;) +
•+ Rule 8



H
- (Ii)
Rule 8
.. OH




k•+
- (H70)
Rule 9 .. +

,Answers for Student Exercises 1 .1 to 1 .5 5

Atom Type # of Atoms Mass Total Mass
Hydrogen 22 1.00783 22.17226
COOH Carbon 11 12.00000 132.00000
Nitrogen 0 14.0031 0.00000
3,5,7-trimethyloctanoic acid
Oxygen 2 15.9949 31.98980
C11H2202
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 1 Exact Mass 186.16206




- (OH•)

Rule 8



+
• 0 0
OH
Rule 8
..
- (C10H21 ) Ill
'OcH II
+C...,
OH
+,..,..H +
0 OH
- (C9H13)
Rule 9
.. HO
A..... • HO
HO
Atom Type # of Atoms Mass Total Mass
Hydrogen 14 1.00783 14.10962
h
OH Carbon 6 12.00000 72.00000
Nitrogen 0 14.0031 0.00000
hexan-1-ol
Oxygen 1 15.9949 15.99490
C6H140
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 0 Exact Mass 102.10452
H
I •



Rule 9


- (CsH1•1 )
OH
•+ Rule 8


•
- (H ) +
OH ··
OH
•+ Rule 8

,
,Answers for Student Exercises 1.1 to 1.5 5

Atom Type # of Atoms Mass Total Mass
Hydrogen 18 1.00783 18.14094
Carbon 8 12.00000 96.00000
OH
Nitrogen 0 14.0031 0.00000
2-methylheptan-2-ol Oxygen 1 15.9949 15.99490
C8H180
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 0 Exact Mass 130.13584
•
- (CsH11 )
OH
•+ Rule 8

- (CH• )
3
OH OH
•+ Rule 8

H
I•



J7 Rule 8


Atom Type
Hydrogen
Rule 8


# of Atoms
16
..
- (CH2= C (CH3h)



Mass
1.00783
Total Mass
16.12528
s Carbon 7 12.00000 84.00000
butyl(propy1)sulfane Nitrogen 0 14.0031 0.00000
C7H16S Oxygen 0 15.9949 0.00000
Sulfur 1 31.9721 31.97210
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1= 0 Exact Mass 132.09738




Rule 8




=SH
+
Rule 9




s
Rule 8 +

, @SOLUTIONSSTUDY

Atom Type # of Atoms Mass Total Mass
k
Hydrogen 20 1.00783 20.15660
Carbon 13 12.00000 156.00000
Nitrogen 0 14.0031 0.00000
(2-hexylphenyl)methanol Oxygen 1 15.9949 15.99490
C13H200 Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 4 Exact Mass 192.15150


or


- (CsH1•1 )
..
r
Rule 7


- (OH•)
Rule 7 ..
- (H)O)
Rule 9
..
0 Atom Type # of Atoms Mass Total Mass


'd U ..,,::. ..,,::.
N0
(4-nitrophenyl )(phenyl)methanone
2
Hydrogen
Carbon
Nitrogen
Oxygen
9
13
1
3
1.00783
12.00000
14.0031
15.9949
9.07047
156.00000
14.00310
47.98470
C 13H9 N03
Sulfur 0 31.9721 0.00000
CnHmXxNyOz IHD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 10 Exact Mass 227.05827


- (C5H4NO;)

.. d+"::
0


Rule 7&8
0N0 2


d+ - (CO)
Rule 8&9 o+
+u
0
(C5H5 )
• .. I "::
-
Rule 7&8
N0 2 N0 2