The accepted mechanism for a rearrangement reaction is shown below. "Q Ph Ph Ph OH Ph J L G Ph Ph HO O (i) (ii) (iii) HO™ fast slow fast HQ Ph LO™ Ph Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining.
The accepted mechanism for a rearrangement reaction is shown below. "Q Ph Ph Ph OH Ph J L G Ph Ph HO O (i) (ii) (iii) HO™ fast slow fast HQ Ph LO™ Ph Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Question
Transcribed Image Text:The accepted mechanism for a rearrangement reaction is shown below.
"Q Ph
(1)
(ii)
Ph
Ph
HO™
fast
Ph
Ph
HO O™
slow
Ph
aufae
.Ar²
LOH
HO™
fast
Draw a curly arrow mechanism for this transformation.
Sketch an energy profile for this reaction, showing approximate relative energies for the
reactants, intermediates, transition states, and products.
HQ Ph
(iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™.
Explain why this result shows that the third step is fast and cannot be rate-determining.
Ph
(iv) Write the predicted rate equation for this mechanism, and show how it was derived.
(v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃
labelling experiment that would allow you to distinguish which of the two aryl groups had
migrated in this situation.
OH
AR²0-
Ar¹
C
C
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