Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134649771
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 11, Problem 40P
A student added an equivalent of 3,4-epoxy-4-methykyclohexanol to a solution of methylmagnesium bromide in diethyl ether, and then added dilute hydrochloric acid. He expected that the product would be 1,2-dimethyl-1,4-yclohexanodiol. He did not get any of the expected product. What product did he get?
3,4-epoxy-4-methyl-cyclohexanol
1,2-dlmethyl-1,4-cydohexanediol
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Complete boxes in the flow chart. Draw the structure of the organic compound foundin each layer after adding 3M NaOH and extraction. Make sure to include any charges. Provide explanation on answers.
==
Vid4Q2
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Provide IUPAC name of product in the reaction
below
A 3,4-dimethylcyclohexene
B 1,2-dimethylcyclohexane
C 1,2-dimethylcyclohexene
D 3,4-dimethylcyclohexane
H₂
Pd
5.
Use the MS data to answer the questions on the next page.
14.0
1.4
15.0
8.1
100-
MS-IW-5644
26.0
2.8
27.0
6.7
28.0
1.8
29.0
80
4.4
38.0
1.0
39.0
1.5
41.0
1.2
42.0
11.2
43.0
100.0
44.0
4.3
79.0
1.9
80.0
2.6
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40
81.0
1.9
82.0
2.5
93.0
8.7
20-
95.0
8.2
121.0
2.0
123.0
2.0
136.0
11.8
0
138.0
11.5
20
40
8.
60
a.
Br
- 0
80
100
120
140
160
180
200
220
m/z
Identify the m/z of the base peak and molecular ion.
2
b.
Draw structures for each of the following fragments (include electrons and charges): 43.0, 93.0,
95.0, 136.0, and 138.0 m/z.
C.
Draw a reasonable a-fragmentation mechanism for the fragmentation of the molecular ion to
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6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium
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Chapter 11 Solutions
Organic Chemistry Study Guide and Solutions Manual, Books a la Carte Edition (8th Edition)
Ch. 11.1 - Prob. 1PCh. 11.2 - Which is more reactive an organolithium compound...Ch. 11.2 - Prob. 3PCh. 11.3 - Muscalure is the sex attractant of the common...Ch. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Prob. 9PCh. 11.3 - Prob. 10PCh. 11.4 - Prob. 13PCh. 11.4 - Prob. 14P
Ch. 11.4 - Prob. 15PCh. 11.4 - Prob. 16PCh. 11.4 - Prob. 17PCh. 11.4 - Prob. 19PCh. 11.4 - Show how the Suzuki and/or Heck reactions can be...Ch. 11.4 - Identify two pairs of an alkyl bromide and an...Ch. 11.5 - Prob. 22PCh. 11.5 - Draw the product of ring-closing metathesis for...Ch. 11.5 - Prob. 25PCh. 11.5 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - The coupling of an alkyne with an aryl halide in...Ch. 11 - Identify A through H.Ch. 11 - Using the given starting material, any necessary...Ch. 11 - What alkyl halide reacts with lithium...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - The following compound undergoes an intramolecular...Ch. 11 - Using ethynyleyclohexane as a starting material...Ch. 11 - Prob. 37PCh. 11 - Using the given starting material, any necessary...Ch. 11 - Prob. 39PCh. 11 - A student added an equivalent of...Ch. 11 - Using the given starting material, any necessary...Ch. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Bombykol is the sex pheromone of the silk moth....Ch. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - A dibromide loses only one bromine when it reacts...Ch. 11 - What starting material is required in order to...Ch. 11 - What product is obtained from ring-opening...
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