ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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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
curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show
explicitly ALL bonds being broken or formed.
Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of
electrophile involved in the nucleophilic attack. MO diagrams are not necessary.
(a).
(b).
-CHO
2. H₂O
1. LiAlH4
2. H₂O
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(a) What monobromo allylic substitution products would result from reaction of each of PRACTICE P
the following compounds with NBS in the presence of peroxides and/or light? (b) In the
case of isomeric products for any reaction, which would you predict to be the most stable
based on the double bond in the product? (c) Draw the resonance hybrid(s) for the allylic
radical that would be involved in each reaction.
(i)
(ii)
V
dil....
(iii)
oily
(3) HI does not undergo free radical addition with 1-butene, even in the presence
of a peroxide. Please provide an explanation by analyzing the propagation
steps if the same radical reaction occurred with HI. Besides the bond
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)
Chapter 10 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
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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