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Exam (elaborations)

Answers for Student Exercises — Spectrometric Identification of Organic Compounds, 8th Edition (Silverstein) — Exercise Answer Key and Spectral Interpretations

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This document is the complete answer key for the student exercises that accompany Spectrometric Identification of Organic Compounds (8th ed., Silverstein). It contains worked answers, spectral assignments, fragment analyses, and explanation notes for problems covering IR, NMR (¹H and ¹³C), mass spectrometry, and combined spectrometric structure elucidation. The material includes molecular formulas, exact masses, degrees of unsaturation, typical fragmentations, coupling patterns, chemical-shift assignments, and suggested structures for the textbook exercises. The answers are arranged by exercise (chapters and problem sets) and are suitable for self-study, homework checking, and exam preparation.

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Uploaded on
November 21, 2025
Number of pages
126
Written in
2025/2026
Type
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All 8 Chapters Covered




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Spectrometric
ldentif ication 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

- (C2Ḣs•) +


[ r Rule 3
..
[ r - (CḢ2=CḢ2) +
+



Rule 9

b Atom Type # of Atoms Mass Total Mass
Ḣydrogen 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
C 10H 18 Sulfur 0 31.9721 0.00000
CnHmXxNyOz IḢD Bromine 0 78.9183 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 2 Exact Mass 138.14094




[ r •
- (C4Ḣ9 )
.. 0
r
or



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Rule 5 and 6

,Answers for Student Exercises 1 .1 to 1 .5 2




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r r
Rule 6
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, Answers for Student Exercises 1 .1 to 1 .5 3

0 Atom Type # of Atoms Mass Total Mass
Ḣydrogen 18 18.14094
1.00783 156.00000
c
Carbon 13 12.00000 0.00000
2-metḣyl-1-pḣenylḣexan- l- Nitrogen 0 14.0031 15.99490
one C13Ḣ1sO
Oxygen 1 15.9949 0.00000
CnḢmXxNyOz IḢD Sulfur 0 31.9721 0.00000
Index = (n) - (m/2) - (x/2) + (y/2) + 1 = 5 Bromine 0 Exact Mass
78.9183 190.13584




o+
Rule 8

+ +

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

/


- (CO) +

Rule 8+9 O I



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




+
+



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r - C5Ḣ13 ..
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Rule 5 +

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