For Questions 13-15, consider the following oxidation reaction: Cyclohexanol is
ID: 1017494 • Letter: F
Question
For Questions 13-15, consider the following oxidation reaction: Cyclohexanol is dissolved in methylene chloride and reacted with excess pyridinium chlorochromate (PCC). The reaction mixture is gently warmed until the formation of cyclohexanone is complete. . Question 13: How could you follow the progress of the reaction? A. Watch for the change in color of PCC from orange (active) to green (inactive). B. Use TLC to detect the ketone product as a spot with a higher Rf than the alcohol. C. Use IR to follow the disappearance of the OH band around 3400 cm-1 and the appearance of a carbonyl band around 1700 cm-1. D. Use litmus paper to follow the disappearance of the acidic OH. B & C A & C 5 points Save Answer QUESTION 14 How can you conveniently remove PCC and it byproducts from the reaction mixture? PCC and its byproducts are solids and can be simply filtered off with filter paper. PCC and its byproducts are soluble in mild aqueous acid and are removed by washing the product with mild aqueous acid. PCC and its byproducts are destroyed by washing the product with mild aqueous hydroxide. PCC and its byproducts are volatile and simple evaporate with the solvent. 5 points Save Answer QUESTION 15 If a stronger oxidant, like potassium dichromate, had been used instead of PCC, what would be the oxidation product from cyclohexanol? Cyclohexanoic Acid Cyclohexanecarboxylic Acid Cyclohexanone Cyclohexanecarbaldehyde
Explanation / Answer
13. The progress of the reaction can be followed by B. TLC as the ketone will not only have higher Rf but will also be mildly UV active unlike the starting alcohol and C. by use of IR spectroscopy as there will be appearence of peak for the keto group at 1700 cm-1
14. PCC and its by-products can be destroyed by washing the product with mild aqueous hydroxide.
15. Cyclohexanone
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