When 1,2-cyclohexanediol is dehydrated in the presence of concentrated sulfuric acid, the major product is not an alkene. Instead, you get cyclohexanone. Write a reasonable and detailed mechanism for the dehydration of 1,2-cyclohexanediol to form cyclohexanone. Use

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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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

When 1,2-cyclohexanediol is dehydrated in the presence of concentrated sulfuric acid, the major product is not an alkene. Instead, you get cyclohexanone. Write a reasonable and detailed mechanism for the dehydration of 1,2-cyclohexanediol to form cyclohexanone. Use curved
arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the course of this reaction as well as any alternative resonance structures that will help you to account for the formation of the major product observed in this reaction.

Definition Definition Organic compounds that contain at least one double bond between carbon-carbon atoms. The general molecular formula for alkenes with one double bond is C n H 2n .

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