4-Tert-Butylcyclohexanone Lab Report

The objective of this two-part experiment was to in Part I, create 4-tert-butylcyclohexanone via oxidation of 4-tert-butylcyclohexanol to provide a source of ketone for reduction procedures. Part II of the experiment was conducted preforming a series of reduction reactions in effort to asses the diastereoselectivity of aluminum isopropoxide (MPV reduction), sodium borohydride (NaBH4), and L-selectride when reacted with 4-tert-butylcyclohexanone. The methods used for analysis were TLC, IR, and 1HNMR spectroscopy.
An oxidation of 4-tert-butylcyclohexanol was conducted to produce the ketone, 4-tert-butylcyclohexanone using oxidizing reagent, sodium hypochlorite in glacial acetic acid solvent. Glacial acetic acid was used to provide an acidic environment to drive the reaction into equilibrium. Also, glacial acetic acid reacts with the oxygen of sodium hypochlorite to form a compound with a partial positive charge on chlorine. Sodium hypochlorite in the presence of glacial acetic acid (pKa~4.5) accomplishes a rapid equilibrium due to the nucleophilic nature of oxygen’s lone pair on the acidic protons of glacial acetic acid. The unusual cationic character of chlorine provided the source of oxidant [Cl+]. Chlorine underwent nucleophilic attack by the hydroxyl group of

One conformation placed the 4-tert-butyl substituent in most stable, locked the equatorial position with the carbonyl pointing up. Oxidation the 4-tert-cyclohexanol produced a greater amount of the more stable conformer with tert-butyl in the equatorial position relative to the conformer with tert-butyl in the un-favored axial position. The faces of 4-tert-butylcyclohexanone are non-equivalent for nucleophilic attack due to top –face steric hindrance imposed by a tert-butyl group in the equatorial position and the presence of much smaller, axial deuterium atoms adjacent to the carbonyl on the bottom-face of the