Sodium Boronhydride Reduction of Cyclohexanone

Laboratory Report

Experiment 2:

Sodium Boronhydride Reduction of Cyclohexanone

Objective

1. To synthesize cyclohexanol from cyclohexanone by using reduction reaction with sodium borohydride.

2. To determine the percentage yields of product produced.

Introduction

In organic chemistry, a ketone is a compound with the structure RC (=O) R', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group (C=O) bonded to two other carbon atoms. The carbonyl group is polar as a consequence of the fact that the electronegativity of the oxygen center is greater than that for carbonyl carbon. Thus, ketones are nucleophilic at oxygen and electrophilic at carbon. Because the carbonyl group interacts with water by hydrogen bonding, ketones are typically more soluble in water than the related methylene compounds. Ketones are a hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and cannot hydrogen-bond to itself. Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are more volatile than alcohols and carboxylic acids of comparable molecular weights. These factors relate to pervasiveness of ketones in perfumery and as solvents. Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula  NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are used for bleaching wood pulp. The compound is insoluble inether , and soluble in glyme solvents, methanol and water, but reacts with the latter two in the absence of base.

Material and apparatus

Test tubes, ice bath, pipette, pre weighed round bottom flask, separatory funnel, rotoevaporator, IR machine, balance

Chemical

Methanol(CH3OH), cyclohexanone, sodium boronhydride, NaOH solution, dichloromethane, anhydrous sodium...