Question

Chemical Synthesis Tutorial: Oxidation of Secondary Alcohol to Ketone

Answer 1

\({\bf{Overview:}}\) in this tutorial I will be going over one particular type of oxidation, the Jones oxidation, using K2Cr2O7 as the oxidizing agent via an ester intermediate

Answer 2

in this particular experiment we synthesized a 2,4-DNP (2,4-dinitrophenylhydrazone) derivative by reacting the ketone from the previous step w/ 2,4-DNP. note* requires dropwise addition of H2SO4 to prime the ketone for substitution

Answer 3

the positive charge on the nitrogen is relieved via proton transfer to the OH, which then makes the OH into a good LG for elimination, making a DB between the two nitrogens. water de-protonates the last H on the positive nitrogen to get

Answer 4

\({\bf{Safety~Information:}}\)
- chromic acid is a very strong oxidizer and gets its own container since it will be incompatible with most waste products
- DNP also gets its own container in this experiment
- recrystallization, since it's done w/ ethanol, goes into non-halogented organic waste