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 6PP
Interpretation Introduction
Interpretation:
The percentage of the products formed by the chlorination of the given reactants is to be determined. Also, the reactivity order of hydrogen atoms is to be compared.
Concept introduction:
The product percentage of the compounds is calculated by the formula:
The reactivity and product percentage vary directly. The hydrogen atoms that are more reactive will convert easily into products and will give more yields.
However, the actually yield and theoretical yield do not always match. They may vary and the exact trend for the reactivity is on the basis of the actual yield and not the theoretical yield.
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Practice Problem 7.16
When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound
called camphene and not bornylene, as one might expect. Using models to assist you, write a step-by-step mechanism
showing how camphene is formed.
HO
H,O
not
heat
Isoborneol
Camphene
Bornylene
4. (3) For each of the following reactions, fill in the missing reagents from the list provided for the
formation of the product shown. Sequential steps, if necessary, should be numbered. Reagents
may be used more than once.
Reagent List:
Lit
NaH NaNH2
Na+
H,C-S-CI
HBr
PBr3
H20
Br2
Li-CH3
но
NaOH
Br-CH3
KBr
(HOAC)
(pyridine)
(LDA)
(MSCI)
но
Br. Br
5. (5) In reaction A, the product was determined to be racemic (both enantiomers were formed).
(a) Propose a curved arrow mechanism for reaction A that accounts for this observation.
(b) Predict the product for reaction B where conditions now use a different chloride source.
b)
H-CI
но
CI
1. LICI
2. HCI
reaction A
reaction B
8. (a) Benzene derivatives exhibit medium to
strong absorption in UV-region. Explain
why aniline and phenoxide ion have
strong UV-absorptions.
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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