ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
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Question
Chapter 10.10, Problem 44P
Interpretation Introduction
Interpretation:
The major product of given should be given.
Concept introduction:
Hofmann elimination:
Quaternary ammonium ion undergoes elimination with strong base like hydroxide ion, this reaction is called as Hofmann elimination. In this reaction, the abstraction of proton form β- carbon, which is having more number of hydrogen to produce the
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Relative Intensity
Part VI. consider the multi-step reaction below for compounds
A, B, and C.
These compounds were subjected to mass spectrometric analysis and
the following spectra for A, B, and C was obtained.
Draw the structure of B and C and match all three compounds
to the correct spectra.
Relative Intensity
Relative Intensity
100
HS-NJ-0547
80
60
31
20
S1
84
M+
absent
10
30
40
50
60
70
80
90
100
100-
MS2016-05353CM
80-
60
40
20
135 137
S2
164 166
0-m
25
50
75
100
125
150
m/z
60
100
MS-NJ-09-43
40
20
20
80
45
S3
25
50
75
100
125
150
175
m/z
Part II. Given two isomers: 2-methylpentane (A) and 2,2-dimethyl butane (B) answer the following:
(a) match structures of isomers given their mass spectra below (spectra A and spectra B)
(b) Draw the fragments given the following prominent peaks from
each spectrum:
Spectra A m/2 =43 and 1/2-57
spectra B m/2 = 43
(c) why is 1/2=57 peak in spectrum A more intense compared
to the same peak in spectrum B.
Relative abundance
Relative abundance
100
A
50
29
29
0
10
-0
-0
100
B
50
720
30
41
43
57
71
4-0
40
50
60 70
m/z
43
57
8-0
m/z = 86
M
90 100
71
m/z = 86
M
-O
0
10 20 30
40 50
60
70
80
-88
m/z
90
100
Part IV. C6H5 CH2CH2OH is an aromatic compound which was subjected to Electron Ionization - mass
spectrometry (El-MS) analysis. Prominent m/2 values: m/2 = 104 and m/2 = 9) was obtained.
Draw the structures of these fragments.
Chapter 10 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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