Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 10, Problem 12PP
Practice Problem 10.12
Benzylic radicals, due to the adjacent benzene ring, have even greater possibility for delocalization than allylic radicals. Draw contributing resonance structures that show this delocalization for the benzylic radical derived from methyl benzene. (Hint: There are four contributing resonance structures for this benzylic radical.)
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Both bicyclo[3.3.1]nonane and bicyclo[2.2.1]heptane are saturated hydrocarbons composed of only 2° and 3° carbons.
Recall that radical substitution generally takes place preferentially at a 3° carbon. Indeed, when bicyclo[3.3.1]nonane is
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models of each of these compounds.
BrCCl.
hv
hv
Br
Br
Bicyclo[3.3.1]nonane
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Bicyclo[2.2.1]heptane
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Following is an example of a type of reaction known as a Diels-Alder reaction
1,3-Pentadiene
Ethylene
3-Methylcyclohexene
(a racemic mixture)
The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is
one of the few ways that chemists have to form two new carbon-carbon bonds in a single
reaction. Given what you know about the relative strengths of carbon-carbon sigma and
pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic?
Explain your reasoning.
Draw an orbital correlation diagram for the suprafacial-suprafacial reaction of an allyl species with an olefin to give the
corresponding cyclopentyl species, and establish whether the reaction is allowed or forbidden for the cation, anion, and
radical.
= 0.
5 Draw the orbital correlation diagram for the addition of ozone to ethylene to give a five-membered ring ozonide.
Is the reaction allowed or forbidden?
6. Predict the product of the following reaction. The reaction involves an intermediate (I) which sets the stereochemistry in
the product. What is this intermediate, and what is the stereochemistry of the product? (Hint: The first reaction involves
a pericyclic C-C bond cleavage.)
Ph
I
N
Heat
H₂CO₂C CO₂CH3
H_CO,C-C=C-CO,CH,
P
diene interconversion of Eq. 15.18.
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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