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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