Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 10, Problem 11PP
Interpretation Introduction
Interpretation: The allylic monobromo substitution products for the given compounds, the most stable isomeric product based on the double bond, and the resonance hybrid(s) for allylic radicals that are formed in each are to be discussed.
Concept introduction:
Molecules that have one unpaired electron are called free radicals.
A
Allylic bromination take place in the presence of NBS and peroxide or light. NBS is a good reagent for allylic bromination.
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For each of the following, write the major product(s) and then draw out each step in the mechanism using
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(a).
(b).
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dissociation enthalpies in the appendix, the following approximate bond
dissociate enthalpies might be useful to you:
~310 kJ/mol
The component of C=C
CH3CH₂CH₂CH₂-Br
CH3CH₂CH₂CH2-I
-290 kJ/mol (C-Br bond)
~235 kJ/mol (C-I bond)
11.;
(a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction
below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation
steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46
kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'.
hv
H-H + Br-Br
2 H-Br
(b) Calculate the overall AH for the above propagation steps (show all work).
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 - 10.32 Synthesize each of the following compounds...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 35PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - Prob. 37PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 39PCh. 10 - Prob. 40PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...Ch. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - 10.2 In the radical chlorination of methane, one...Ch. 10 - Prob. 3QCh. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - Prob. 5QCh. 10 - Prob. 6Q
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