Scribd
Upload
263 views2 pages

Prelab For Cyclohexanone Synthesis From Cyclohexanol

This document discusses the oxidation of cyclohexanol to cyclohexanone. Cyclohexanol is a secondary alcohol that can be oxidized to form the ketone cyclohexanone. Sodium hypochlorite in acidic solution will be used as the oxidizing agent to perform this reaction. The product cyclohexanone will be characterized using Jones reagent, warm potassium permanganate, and Brady's reagent to confirm its identity and purity. The student will learn about alcohol oxidation mechanisms and characterize their cyclohexanone product.

Uploaded by

Sollen Lataquin
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
263 views2 pages

Prelab For Cyclohexanone Synthesis From Cyclohexanol

This document discusses the oxidation of cyclohexanol to cyclohexanone. Cyclohexanol is a secondary alcohol that can be oxidized to form the ketone cyclohexanone. Sodium hypochlorite in acidic solution will be used as the oxidizing agent to perform this reaction. The product cyclohexanone will be characterized using Jones reagent, warm potassium permanganate, and Brady's reagent to confirm its identity and purity. The student will learn about alcohol oxidation mechanisms and characterize their cyclohexanone product.

Uploaded by

Sollen Lataquin
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
You are on page 1/ 2

Alcohols are organic compounds with a hydroxyl group attached to an alpha carbon.

Alcohols
can be classified depending on the amount of alkyl groups connected to its respective alpha carbon, the
classifications are primary, secondary and tertiary:

Fig1.1 types of alcohols

Of all these types, only tertiary alcohols cannot undergo oxidation, however, if a primary or secondary
alcohol undergoes oxidation, a new compound belonging to another class will be formed, in the case of
a secondary alcohol, ketones will be formed after oxidation. In small scale organic synthesis applications,
ketones are often prepared by oxidation of secondary alcohols.

In the experiment, cyclohexanone, a ketone, will be synthesized from cyclohexanol, a secondary


alcohol. The obtained product will then be purified, and characterized. The student should be able to
explain the mechanisms of primary and secondary alcohol oxidation, explain the mechanism of the jones
reagent with an alcohol, and successfully obtain a relatively high yield of a relatively pure cyclohexanone
product after the experiment.

Fig.1.2 overall reaction

Strong oxidants are most commonly used in these reactions such as potassium permanganate or
a Cr (VI) containing compound, these however are relatively expensive. It is therefore imperative to
continue the synthesis using a different yet cheaper oxidant such as sodium hypochlorite (an active
ingredient in household chlorine bleach) in an acidic solution. The hypochlorite ions containing a
positively charged chloronium ion can be produced by adding sodium hypochlorite to an acidic solution:

Fig 1.3 hypochlorite production

The hypochlorite ion can then impart its chloronium ion to the cyclohexanol producing cyclohexanone:

Fig 1.4 overall mechanism

The recovered product will then be tested with the Jones reagent, a chromium trioxide solution
in sulfuric acid. The reaction of a secondary alcohol with the jones reagent goes as follows:

Fig 1.5 overall reaction

Due to the reduction of Chromium (VI) from chromic acid (which is orange – yellow in color) to
Chromium (III) (which is blue green in color) with the existence of an alcohol, it is valid to conclude that
if the product turned out positive results in the Jones test (with the said color change), the starting
material wasn’t completely oxidized into the desired product.

The product will also be tested with warm, dilute KMnO4 - another strong oxidizing agent. The
production of MnO2 in the reaction (which is brown in nature) will dictate whether the test resulted
positive or not. The reaction of alcohols with warm KMno4 goes as follows:

Fig 1.6 over all reaction

It is therefore valid to say that if the product tested positive with the warm KMnO4, the starting material
wasn’t completely oxidized into the desired product.
The obtained product can also be tested for the existence of cyclohexanone by using Brady’s
reagent : 2,4 – DNP. The reaction goes as follows:

Fig 1.7 overall reaction

The product formed, 2,4 – dinitrophenylhydrazone , is a yellow – red precipitate. The production of a
yellow-red precipitate after the reaction of the obtained product and 2,4 – DNP will therefore conclude
that there is cyclohexanone present in the product. The boiling point of the product will also be
obtained by the oil-bath method, the expected boiling point value is 155.6 C.

You might also like