Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
3rd Edition
ISBN: 9780134255644
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 8, Problem 47P
Starting with bromocyclohexane, how could the following compounds be prepared?
Expert Solution & Answer
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Part I.
a) Elucidate
the structure of compound A using the following information.
• mass spectrum: m+ = 102, m/2=57
312=29
• IR spectrum:
1002.5
% TRANSMITTANCE
Ngg
50
40
30
20
90
80
70
60
MICRONS
5
8
9 10
12
13
14 15 16
19
1740 cm
M
10
0
4000
3600
3200
2800
2400
2000
1800
1600
13
• CNMR
'H
-NMR
Peak
8
ppm (H)
Integration
multiplicity
a
1.5 (3H)
triplet
b
1.3
1.5 (3H)
triplet
C
2.3
1 (2H)
quartet
d
4.1
1 (2H)
quartet
& ppm (c)
10
15
28
60
177 (C=0)
b) Elucidate the structure of compound B using the following information
13C/DEPT NMR 150.9 MHz
IIL
1400
WAVENUMBERS (CM-1)
DEPT-90
DEPT-135
85 80 75
70
65
60
55
50
45 40
35
30 25 20
ppm
1200
1000
800
600
400
•
Part II.
a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below:
• IR spectra
% TRANSMITTANCE
1002.5
90
80
70
60
50
40
30
20
10
0
4000
3600
3200
2800
2400
2000
1800
1600
• Information from 'HAMR
MICRONS
8 9 10
11
14 15 16
19
25
1400
WAVENUMBERS (CM-1)
1200
1000
800
600
400
peak
8 ppm
Integration
multiplicity
a
2.1
1.5 (3H)
Singlet
b
3.6
1 (2H)
singlet
с
3.8
1.5 (3H)
Singlet
d
6.8
1(2H)
doublet
7.1
1(2H)
doublet
Information from 13C-nmR
Normal carbon
29ppm
Dept 135
Dept -90
+
NO peak
NO peak
50 ppm
55 ppm
+
NO peak
114 ppm
t
126 ppm
No peak
NO peak
130 ppm
t
+
159 ppm
No peak
NO peak
207 ppm
по реак
NO peak
Could you redraw these and also explain how to solve them for me pleas
Chapter 8 Solutions
Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
Ch. 8.1 - Prob. 2PCh. 8.1 - Does increasing the energy barrier for an SN2...Ch. 8.1 - Arrange the following alkyl bromides in order from...Ch. 8.2 - Prob. 7PCh. 8.2 - Which reaction in each of the following pairs...Ch. 8.2 - Prob. 9PCh. 8.2 - Prob. 11PCh. 8.3 - Draw the substitution products that will be formed...Ch. 8.4 - Arrange the following alkyl halides in order from...Ch. 8.5 - Prob. 14P
Ch. 8.5 - Which of the following reactions will go faster if...Ch. 8.6 - After a proton is removed from the OH group, which...Ch. 8.6 - Draw the product of each of the following...Ch. 8.9 - Prob. 20PCh. 8.9 - Prob. 21PCh. 8.11 - Why do the SN1/E1 reactions of tertiary alkyl...Ch. 8.11 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.12 - Prob. 25PCh. 8.12 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - a In which solvent would tert-butyl bromide...Ch. 8.13 - What would be the best way to prepare the...Ch. 8 - Methoxychlor is an insecticide that was intended...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Explain how the following changes would affect the...Ch. 8 - Prob. 38PCh. 8 - Draw the major product obtained when each of the...Ch. 8 - Which alkyl halide in Problem 39 can undergo an El...Ch. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Starting with bromocyclohexane, how could the...Ch. 8 - Prob. 48PCh. 8 - Fill in the blanks in the following chemical...Ch. 8 - For each of the following alkyl halides, indicate...Ch. 8 - Prob. 51PCh. 8 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 8 - An ether can be prepared by an SN2 reaction of an...Ch. 8 - Give two sets of reactants (each set including an...Ch. 8 - Show how the following compounds could be...Ch. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Draw the structures of the products obtained from...Ch. 8 - cis-4-Bromocyclohexanol and...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - In which solventethanol or diethyl etherwould the...Ch. 8 - The pKa of acetic acid in water is 4.76. What...
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- In the image, the light blue sphere represents a mole of hydrogen atoms, the purple or teal spheres represent a mole of a conjugate base. A light blue sphere by itself is H+. Assuming there is 2.00 L of solution, answer the following: The Ka of the left & right solution is? The pH of the left & right solution is? The acid on the left & right is what kind of acid?arrow_forwardNonearrow_forwardNonearrow_forward
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