Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
9th Edition
ISBN: 9781305922198
Author: John E. McMurry
Publisher: CENGAGE L
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Question
Chapter 14.SE, Problem 16VC
Interpretation Introduction
Interpretation:
The structures of all possible adducts obtainable when the diene given reacts with one equivalent of HCl are to be given.
Concept introduction:
Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.
To give:
The structures of all possible adducts obtainable when the diene given reacts with one equivalent of HCl.
Expert Solution & Answer
Answer to Problem 16VC
The compound given is 1-vinylcyclopentene.The structures of all the possible adducts obtained when it reacts with one equivalent of HCl are given below.
Explanation of Solution
1-Vinylcyclopentene is an unsymmetrical conjugated diene. Protonation of the CH2 in double bond and that in the ring lead to the formation of two different allyl carbocations, each of which is in resonance with another form. Hence four carbocations as shown are possible. Attack of the chloride ion on each of these carbocation leads to the formation of four different products.
Conclusion
The compound given is 1-vinylcyclopentene.The structures of all the possible adducts obtained, when it reacts with one equivalent of HCl, are given below.
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Students have asked these similar questions
Part VII. The H-NMR of a compound with molecular formula C5 H 10 O2 is given below.
Find the following:
(a) The no. of protons corresponding to each signal in the spectra
(6) Give the structure of the compound and assign the signals to each
proton in the compound.
a
70.2
Integration Values
C5H10O2
b
47.7
C
46.5
d
69.5
3.6 3.5
3.4 3.3 3.2 3.1 3.0
2.9 2.8
2.7
2.6 2.5
2.4 2.3 2.2 2.1 2.0
Chemical Shift (ppm)
1.9
1.8
1.7 1.6
1.5
1.4 1.3 1.2
1.1 1.0
0.9 0.8
Part 111. 1 H-NMR spectrum of a compound with integration values in red is given below.
Answer the following:
(a) write the signals in the 'H-NMR spectrum to the corresponding protons on the structure
of the molecule below.
(b) Identify the theoretical multiplicities for each proton in the compound. Also give the possible.
complex splitting patterns assuming J values are not similar.
там
Br
22
2
3
6
4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0
Chemical Shift (ppm)
ra.
Br
2
3
6
6
2.5
2.4
2.3
2.2
2.1
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.1
1.0
0.9
0.8
Chemical Shift (ppm)
2
2
Br
7.3
7.2
7.1
7.0 6.9
6.7 6.6 6.5
6.4
6.3
6.2
6.1
6.0
Chemical Shift (ppm)
5.9
5.8 5.7
5.5 5.4 5.3 5.2
5.0 4.9
1600°
1538°C
1493°C
In the diagram, the letter L indicates
that it is a liquid. Indicate its
components in the upper region
where only L is indicated.
The
iron-iron carbide phase
diagram.
Temperature (°C)
1400
8
1394°C
y+L
1200
2.14
y, Austenite
10000
912°C
800a
0.76
0.022
600
400
(Fe)
a, Ferrite
Composition (at% C)
15
1147°C
a + Fe3C
2
3
Composition (wt% C)
L
2500
4.30
2000
y + Fe3C
727°C
1500
Cementite (Fe3C)
1000
4
5
6
6.70
Temperature (°F)
Chapter 14 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
Ch. 14.1 - Prob. 1PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5PCh. 14.3 - Prob. 6PCh. 14.5 - Predict the product of the following Diels–Alder...Ch. 14.5 - Prob. 8PCh. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Diels–Alder...
Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
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