Oxidation of Cyclohexanol
Oxidation of Cyclohexanol
Introduction:
The oxidation of cyclohexanol involves using household bleach to oxidize this secondary alcohol and produce a ketone product, cyclohexanone. Oxidation-reduction (redox) reactions occur when the oxidation state of atoms change due to a transfer of electrons. Oxidation occurs when electrons are ‘lost’ to the formation of bonds and reduction occurs when electrons are ‘gained’ in the braking of bonds (Levine). Using this reaction and its product, a redox experiment was performed to familiarize students with important organic chemistry laboratory techniques including proper mixing in an oxidation reaction, extraction, infrared spectroscopy, and gas chromatography. Reactants cyclohexanol and sodium hypochlorite (NaOCl) undergo a redox reaction and when combined with the catalyst acetic acid (HOAc) and solvent water (H2O), form the product cyclohexanone along with sodium chloride (NaCl) and water. In the overall
Figure 1: Cyclohexanol Reaction
oxidation-reduction reaction, the secondary alcohol of cyclohexanol is oxidized to form the ketone cyclohexanone, and the Cl of NaOCl is reduced to form NaCl.
This reaction utilizes the catalyst acetic acid to speed up the reaction by forming HOCL when the nucleophile OCl- removes the acidic H from acetic acid. This same H bonds to the oxygen of cyclohexanol and the OCl- attaches to the carbon the alcohol group was attached
to at the same time water is removed. Next, the water removes the acidic hydrogen, which allows a double bond to oxygen to form and the chlorine ion to detach. This leaves cyclohexanone, the chloride ion and hydrodium ion. This particular reaction is considered
environmentally friendly or good ‘Green Chemistry’ based on four principles: atom economy, no organic solvent required, use of a catalyst, and microscale. Atom economy means that the ratio of atoms consumed to those produced is close to one. This is only one way to oxidize cyclohexanol that is
Introduction:
The oxidation of cyclohexanol involves using household bleach to oxidize this secondary alcohol and produce a ketone product, cyclohexanone. Oxidation-reduction (redox) reactions occur when the oxidation state of atoms change due to a transfer of electrons. Oxidation occurs when electrons are ‘lost’ to the formation of bonds and reduction occurs when electrons are ‘gained’ in the braking of bonds (Levine). Using this reaction and its product, a redox experiment was performed to familiarize students with important organic chemistry laboratory techniques including proper mixing in an oxidation reaction, extraction, infrared spectroscopy, and gas chromatography. Reactants cyclohexanol and sodium hypochlorite (NaOCl) undergo a redox reaction and when combined with the catalyst acetic acid (HOAc) and solvent water (H2O), form the product cyclohexanone along with sodium chloride (NaCl) and water. In the overall
Figure 1: Cyclohexanol Reaction
oxidation-reduction reaction, the secondary alcohol of cyclohexanol is oxidized to form the ketone cyclohexanone, and the Cl of NaOCl is reduced to form NaCl.
This reaction utilizes the catalyst acetic acid to speed up the reaction by forming HOCL when the nucleophile OCl- removes the acidic H from acetic acid. This same H bonds to the oxygen of cyclohexanol and the OCl- attaches to the carbon the alcohol group was attached
to at the same time water is removed. Next, the water removes the acidic hydrogen, which allows a double bond to oxygen to form and the chlorine ion to detach. This leaves cyclohexanone, the chloride ion and hydrodium ion. This particular reaction is considered
environmentally friendly or good ‘Green Chemistry’ based on four principles: atom economy, no organic solvent required, use of a catalyst, and microscale. Atom economy means that the ratio of atoms consumed to those produced is close to one. This is only one way to oxidize cyclohexanol that is