Oxidation
YOUR NAME: Erin Alston, Kennedy Stuart, Amber Lamb and Stephonya Williams
EXPERIMENT TITLE: Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation and Adipic Acid from Cyclohexanone
DATE: 4/18/2014
INTRODUCTION: In experiment 4, alcohol is oxidized to a ketone with household bleach. The product is then isolated by steam distillation and is extracted into the distillate with ether. After the removal of ether, it leaves the product cyclohexanone.
In experiment 6, cyclohexanone is oxidized by potassium permanganate. Manganese dioxide is filtered off and the filtrate is concentrated, acidified with hydrochloric acid and then cooled to yield crystalline adipic acid.
OBJECTIVE:
Experiment 4: To recover cyclohexanone from the oxidation of cyclohexanol by hypochlorite
Experiment 6: To recover adipic acid from the oxidation of cyclohexanone
CHEMICAL REAGENTS
Cyclohexanol
Acetic Acid
Chlorine (Bleach)
Thymol Blue (indicator)
Sodium Hydroxide
These reagents were all used during experiment 4.
APPARATUS USED
Simple distillation apparatus
250mL round bottomed flask
PROCEDURE: Experiment 4
8 mL of cyclohexanol was placed into a 250 mL Erlenmeyer flask, and then a thermometer was introduced to the cyclohexanol. A mixture of 4 mL of acetic acid and 115mL of commercial household bleach was slowly added to the flask, while swirling it. During adding the mixture, the temperature was kept between 40 degrees C-50 degrees C. The process took 15-20min. Once the 20 minutes was up, the mixture was tested by dropping some of the mixture onto a piece of starch iodide paper. After the test, the reaction was transferred to a 250mL round bottomed flask and was set up for simple distillation. To help with distillation, boiling chips was added. The distillation was continued until 40mL was collected.
Experiment 6
5.0g of cyclohexanone, 15g of potassium permangarate was mixed together with 125mL of water into a 250mL Erlenmeyer flask. Once the mixture was reached
EXPERIMENT TITLE: Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation and Adipic Acid from Cyclohexanone
DATE: 4/18/2014
INTRODUCTION: In experiment 4, alcohol is oxidized to a ketone with household bleach. The product is then isolated by steam distillation and is extracted into the distillate with ether. After the removal of ether, it leaves the product cyclohexanone.
In experiment 6, cyclohexanone is oxidized by potassium permanganate. Manganese dioxide is filtered off and the filtrate is concentrated, acidified with hydrochloric acid and then cooled to yield crystalline adipic acid.
OBJECTIVE:
Experiment 4: To recover cyclohexanone from the oxidation of cyclohexanol by hypochlorite
Experiment 6: To recover adipic acid from the oxidation of cyclohexanone
CHEMICAL REAGENTS
Cyclohexanol
Acetic Acid
Chlorine (Bleach)
Thymol Blue (indicator)
Sodium Hydroxide
These reagents were all used during experiment 4.
APPARATUS USED
Simple distillation apparatus
250mL round bottomed flask
PROCEDURE: Experiment 4
8 mL of cyclohexanol was placed into a 250 mL Erlenmeyer flask, and then a thermometer was introduced to the cyclohexanol. A mixture of 4 mL of acetic acid and 115mL of commercial household bleach was slowly added to the flask, while swirling it. During adding the mixture, the temperature was kept between 40 degrees C-50 degrees C. The process took 15-20min. Once the 20 minutes was up, the mixture was tested by dropping some of the mixture onto a piece of starch iodide paper. After the test, the reaction was transferred to a 250mL round bottomed flask and was set up for simple distillation. To help with distillation, boiling chips was added. The distillation was continued until 40mL was collected.
Experiment 6
5.0g of cyclohexanone, 15g of potassium permangarate was mixed together with 125mL of water into a 250mL Erlenmeyer flask. Once the mixture was reached
References: Kenneth L. Williamson; Robert D. Minard; Katherine M. Masters, Macroscale and Microscale Organic Experiments, Fifth Edition, Boston, 2007, pp 375-388. Procedure: pp383-386.