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Exam (elaborations)

Spectrometric Identification of Organic Compounds (8th Ed. Silverstein) — Exercise Solutions & Explanations

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This document offers detailed explanations and worked‑out solutions for selected student exercises from Spectrometric Identification of Organic Compounds, 8th Edition by Silverstein. It includes interpretations of IR, NMR, MS, and UV spectra and guides students through problem‑solving strategies used in spectrometric analysis of organic compounds.

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Institution
Spectrometric Identification Of Organic Compounds
Course
Spectrometric Identification of Organic Compounds

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All 8 Chapters Covered




Answers for Student Exercises

,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

- (C2H5 )

Rule 3



- (C5H11 )

Rule 3


H - (CH2=CH2)

Rule 9

Atom Type # of Atoms Mass Total Mass
b
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



or




- (C4H9 )

Rule 5 and 6



- (CH2=CH2)
Rule 6



- (C3H7 )

Rule 3

,Answers for Student Exercises 1.1 to 1.5 2

O Atom Type # of Atoms Mass Total Mass
c Hydrogen 18 1.00783 18.14094
Carbon 13 12.00000 156.00000
Nitrogen 0 14.0031 0.00000
2-methyl-1-phenylhexan-1-one Oxygen 1 15.9949 15.99490
C13H18O 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 O O
- (C6H13 )

Rule 8
O O
- (C6H5 )
Rule 8

H
O - (C4H8) O OH

Rule 9 H

O
- (CO)
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



or



- (CH3)
Rule 5


- (C6H13)
Rule 5

H
- (C7H14)
Rule 9

, Answers for Student Exercises 1.1 to 1.5 3
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
1-(hexan-2-yl)benzene Oxygen 0 15.9949 0.00000
C12H18
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


- (CH3 )

Rule 7


- (C4H9 )

Rule 7

H H
- (C4H8 )

Rule 9


H
Atom Type # of Atoms Mass Total Mass
f Hydrogen 16 1.00783 16.12528
OH Carbon 7 12.00000 84.00000
Nitrogen 0 14.0031 0.00000
heptan-2-ol
C7H16O Oxygen 1 15.9949 15.99490
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

- (C5H11 )
OH
Rule 8 OH


- (CH3 )
OH OH
Rule 8

H
- (H )
OH OH
Rule 8

H - (H2O)
OH
Rule 9
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Robert M. Silverstein, Francis X. Webster, David J. Kiemle, David L. Bryce Spectrometric Identification of Organic Compounds
  • 2014
  • 9780470616376
  • Unknown

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Spectrometric Identification of Organic Compounds
Course
Spectrometric Identification of Organic Compounds

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Uploaded on
February 4, 2026
Number of pages
252
Written in
2025/2026
Type
Exam (elaborations)
Contains
Questions & answers

Subjects

  • organic compounds
  • silverstein 8th edition
  • ir spectroscopy
  • nmr spectroscopy
  • mass spectrometry
  • spectrometric identification
  • spectrum interpretation structural elucidation
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