Draw/outline a reasonable and detailed mechanism for the dehydration of 2-methylcyclohexanol catalyzed by phosphoric acid. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the reaction. Predict and rationalize the expected product distribution based on thermodynamic aspects

Draw/outline a reasonable and detailed mechanism for the dehydration of 2-methylcyclohexanol catalyzed by phosphoric acid. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the reaction. Predict and rationalize the expected product distribution based on thermodynamic aspects

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...

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A. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.
Outline a mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid.
Using 2,2-dimethylpropanal and other necessary reagents, write the derivation of 2,4,4-trimethyl-2-pentenal showing the reaction mechanism.
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Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
The reaction of sodium borohydride with ketones proceeds rapidly at room temperature, forming an intermediate borate ester which is hydrolyzed to give the product alcohol: 4 R2C=O + Na+BH4- ---> (R2CHO)4B-Na+ 2. (R2CHO)4B-Na+ + 2H2O ---> 4R2CHOH + Na+BO2- Rewrite these two steps using benzil as the ketone, and using structural formulas throughout, rather than the condensed forms above. For example, the structural formula for water is H-O-H. Please write them by hand and paste them in.
Explain and detail the reaction mechanism: NaBr + H2O + n-butyl alcohol = ?
I'm just wondering, would the answer be that it is possible to create 3-methyl-1-butanol form acidic hydration of 3-methyl-1-butene but you would end up with a mixture of 3-methyl-1-butanol as well as 3-methyl-2-butanol with the latter being the major species?
The reaction of sodium borohydride with ketones proceeds rapidly at room temperature, forming an intermediate borate ester which is hydrolyzed to give the product alcohol: 4 R2C=O + Na+BH4- ---> (R2CHO)4B-Na+ (R2CHO)4B-Na+ + 2H2O ---> 4R2CHOH + Na+BO2- Rewrite these two steps using benzil as the ketone, and using structural formulas throughout, rather than the condensed forms above.