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Oxidation of Secondary Alcohols to Ketones with Household Bleach (NaOCl)

Page history last edited by jbfriesen 9 years, 2 months ago

Adapted from “Experiments in Organic Chemistry by Richard K. Hill & John Barbaro, 2nd

edition, Contemporary Publishing Company of Raleigh, Inc. (2000) 0-89892-218-6

 

Summary of Experiment

Student Handout 2011- this year we varied the reaction time and rate of bleach addition.

Student Handout 2009 for Week One.Week one was the oxidation of 2, 3, or 4-methyl-1-cyclohexanol.

Students were allowed to choose an alcohol for the experiment. The products were analyzed by IR and GC-FID.

 

Positive

+ Generates a nice discussion of green chemistry principles and alternative synthetic applications.

+ Inexpensive and relatively low toxicity!

+ Many analysis opportunities: IR, 1H NMR, 13C NMR, MS spectroscopy; TLC, GC, HPLC, chromatography.

 

Neutral

± odd smells

± successful employment of KI-starch indicator paper is still a mystery to me.

 

Negative

- work up is a tedious liquid-liquid separation process

 

Inquiry and Extension Ideas

● Could be done with any secondary alcohol.

● Simple experiment that can be modified easily without total loss of product.

● Various work-up possibilities.

● Could be beginning of multi-step synthesis: 1) oxidation, 2) Grignard addition, 3) dehydration, 4) addition to double bond….

GC-FID 2011

IR 2011

GC-FID chromatograms 2009

IR Spectra 2009

Photos 2009

Student Comments 2009 1st week

Student Comments 2009 2nd week

 

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