Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 16.SE, Problem 50AP
Name and draw the major product(s) of electrophilic chlorination of the following compounds:
(a) m-Nitrophenol
(b) o-Xylene
(c) p-Nitrobenzoic acid
(d) p-Bromobenzenesulfonic acid
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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
Relative Intensity
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
fragment 43.0 m/z. Be sure to include all electrons and formal charges.
6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium
ion (CsH6N) and show your work.
None
Stereochemistry: Three possible answers- diastereomers, enantiomers
OH
CH₂OH
I
-c=0
21108 1101
41745 HOR
CH₂OH
IL
Но
CH₂OH
TIL
a. Compounds I and III have this relationship with each other: enantiomers
b. Compounds II and IV have this relationship with each other:
c. Compounds I and II have this relationship with each other:
d. *Draw one structure that is a stereoisomer of II, but neither a
diastereomer nor an enantiomer. (more than one correct answer)
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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