Intro exp benzaldehyde of benzylic acid

Multistep synthesis can be defined as the process of converting compounds that commercially
available into desired products by using known reactions. It involves more than one step which the
formation of intermediate is compulsory.

In this experiment, we were supposed to convert benzaldehyde to benzilic acid via a three step of
reactions. Firstly, two equivalents of benzaldehyde react to form benzoin by using thiamine-
catalyzed reaction. Thiamine is used as it acts as a coenzyme that enhances the reaction.Secondly,
benzoin undergoes oxidation to form benzil . Oxidation reaction occurs in order to utilize the mild
oxidizing agent which is nitric acid in pyridine.lastly, benzil rearranges to form benzilic acid by
reactions with KOH and then followed by H3o+. the rearrangement of benzil happens due to the
intramolecular oxidation and reduction forces of gaining and losing electrons. However, we were
failed during first step due to several factors which will be explained more details in the discussion
parts.

Thiamine hydrochloride is used as a “green” reagent as opposed to thiamine pyrophosphate (TPP) to

catalyze the benzoin condensation. In the reaction, the proton at carbon two is removed with a
weak base to form the ylide, which acts as a nucleophile and adds to the carbonyl group of
benzaldehyde. Then another proton is removed with a base to form a double bond, which then
reacts with another equivalent of benzaldehyde to form another intermediate. The base then
removes another proton to yield benzoin and the ylide, which can hen react with more molecules of
benzaldehyde. Next, the benzoin produced in the first step is oxidized with nitric acid to prepare
benzil in the final reaction, the benzil produces is rearranged with potassium hydroxide and then an
acid reaction, the benzil produced is rearranged with potassium hydroxide and then an acid
(hydrochloric acid). The addition of potassium hydroxide to benzil yields a carboxylate salt,
potassium benzilate, which then reacts with an acid to produce the final product< benzilic acid.

Equation 1: Thiamine Catalysis of Benzoin

Equation 2:Oxidation of Benzil

Equation 3: Rearrangement of Benzil to Benzilic Acid

Infrared Spectroscopy (IR) is performed after each step to determine if the desired product is
formed. The 1H and 13C Nuclear Magnetic Resonance Spectroscopy (NMR) of the final product is also
determined to ensure the correct product is created. These spectra can be found in the attached
appendix.