Student's Solutions Manual for Organic Chemistry
9th Edition
ISBN: 9780134160375
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 12, Problem 12.20SP
(A true story) While organizing the undergraduate stockroom a new chemistry professor found a half-gallon jug containing a cloudy liquid (bp 100-105 °C), marked only “STUDENT PREP.” She ran a quick mass spectrum, which is printed below. As soon as she saw the spectrum (without even checking the actual mass numbers), she said, “I know what it is.”
- a. What compound is the “student prep”? Any uncertainty in the structure?
- b. Suggest structures for the fragments at 136, 107, and 93. Why is the base peak (at m/z 57) so strong?
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Name these organic compounds:
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name
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2025 McGraw Hill LLC. All Rights Reserved. Terms of
Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic.
ZI
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O aromatic
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O nonaromatic
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H
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×
Part I.
Draw the stepwise reaction mechanism of each product (a, b, c, d, e, f)
HO
HO
OH
НОН,С
HO
OH
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HO
CH₂OH
H
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N
HO
-H
H
-OH
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H
OH
CH₂OH
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OH
НОН,С
HO
HO
+
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HO-
HO
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OH
HO
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OH
(b)
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HN
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ethanol
H
N
N
N
HO
·H
H
OH
H
OH
N
CH₂OH
OH
(f) Phenyl Osazone
H
(e) Carboxy phenyl osatriazole
Figure 2.1. Reaction Scheme for the Total Synthesis of Fine Chemicals
Chapter 12 Solutions
Student's Solutions Manual for Organic Chemistry
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
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