oxidation of alcohol lab
Oxidation of an Alcohol:
Oxidizing Methoxybenzyl Alcohol to
Methoxybenzaldehyde Using
Phase-Transfer Catalysis
PURPOSE OF THE EXPERIMENT
Oxidize methoxybenzyl alcohol to methoxybenzaldehyde, using sodium hypochlorite as the oxidizing agent and tetrabutylammonium hydrogen sulfate as the phase-transfer catalyst.
Monitor the progress of the reaction by thin-layer chromatography.
BACKGROUND REQUIRED
You should be familiar with extraction, evaporation, and thin-layer chromatography techniques.
You may wish to review the TLC lab from earlier in the semester!
BACKGROUND INFORMATION
In organic molecules, carbon may exist in several different oxidation states. In typical organic compounds, the oxidation number for carbon may vary from –4 (a very reduced form of carbon, such as carbon in methane) to +2 (a very oxidized form of carbon, such as carbon in formic acid), or any oxidation number within this range. [Please note that while it is possible for carbon to have oxidation numbers outside of this range, they are generally not observed for organic molecules]. Reduction and oxidation processes can occur in organic reactions, just as you may remember for inorganic compounds and ions from General Chemistry class. The oxidation number for carbon may increase (an oxidation process) or decrease (a reduction process), depending on the reaction conditions. Oxidation of carbon often can be identified in an organic reaction because the number of carbon-oxygen bonds will increase, and the number of carbon-hydrogen bonds will decrease during the process. Reduction, of course, exhibits the opposite: carbon-hydrogen bonds increase and carbon-oxygen bonds decrease in number. For example, the following reaction is easily identifiable as an oxidation because the number of carbon-oxygen bonds is increasing from two to three; and the number of carbon-hydrogen bonds is decreasing from two to one:
O
H C
O
H
H C OH
A substance which increases the oxidation
Oxidizing Methoxybenzyl Alcohol to
Methoxybenzaldehyde Using
Phase-Transfer Catalysis
PURPOSE OF THE EXPERIMENT
Oxidize methoxybenzyl alcohol to methoxybenzaldehyde, using sodium hypochlorite as the oxidizing agent and tetrabutylammonium hydrogen sulfate as the phase-transfer catalyst.
Monitor the progress of the reaction by thin-layer chromatography.
BACKGROUND REQUIRED
You should be familiar with extraction, evaporation, and thin-layer chromatography techniques.
You may wish to review the TLC lab from earlier in the semester!
BACKGROUND INFORMATION
In organic molecules, carbon may exist in several different oxidation states. In typical organic compounds, the oxidation number for carbon may vary from –4 (a very reduced form of carbon, such as carbon in methane) to +2 (a very oxidized form of carbon, such as carbon in formic acid), or any oxidation number within this range. [Please note that while it is possible for carbon to have oxidation numbers outside of this range, they are generally not observed for organic molecules]. Reduction and oxidation processes can occur in organic reactions, just as you may remember for inorganic compounds and ions from General Chemistry class. The oxidation number for carbon may increase (an oxidation process) or decrease (a reduction process), depending on the reaction conditions. Oxidation of carbon often can be identified in an organic reaction because the number of carbon-oxygen bonds will increase, and the number of carbon-hydrogen bonds will decrease during the process. Reduction, of course, exhibits the opposite: carbon-hydrogen bonds increase and carbon-oxygen bonds decrease in number. For example, the following reaction is easily identifiable as an oxidation because the number of carbon-oxygen bonds is increasing from two to three; and the number of carbon-hydrogen bonds is decreasing from two to one:
O
H C
O
H
H C OH
A substance which increases the oxidation