Chemical Chirality - Results Sheet G Question 5

Alan Lai

The chiral resolution involved forming diastereomeric salts that had different

solubilities in order to separate the two enantiomers of mandelic acid. Its advantages include

the ability to separate a mixture of enantiomers, so that we can obtain one specific

enantiomer. Additionally, it yields a high purity, especially for that of the solid if the two

enantiomers differ by solubility, upwards of about 80 to 90%. However, it has disadvantages

in that the enantiomer in solution has a lower purity, and that if only one enantiomer is

desired, then large quantities (half, corresponding to the other enantiomer) is wasted.

The enzymatic reduction used yeast enzymes in order to reduce methyl

benzoylformate to methyl mandelate. It has multiple advantages - the yeast and sucrose

needed to support the reaction is very inexpensive, and little attention is needed to keep the

reaction going. Additionally, it is extremely enantiomerically selective, with ee of around

98%. Furthermore, an enzymes reusability allows it to react with more reactants than

synthetic reactions. Its mediated reactivity and substrate selectivity also prevents unwanted

reactions from occurring, such as creation of hydrogen gas, and is very safe to operate.

However, a few disadvantages include a lower yield, and the time needed for the reaction to

run sufficiently. Additionally, further purification techniques are needed, which contributes to

the lower yield, and there are no visible signs of the reaction occurring.

Racemic reduction provided both enantiomers of methyl mandelate through the

reduction of methyl benzoylformate using NaBH4. Advantages include its relatively fast

reaction time, and its simplicity in implementation. However, it is disadvantaged by the fact

that a racemic mixture is produced. This means if one enantiomer is preferred over the

other, we will not be able to make a specific enantiomer. Additionally, the reactivity of sodium
borohydride is also a liability. Its high reactivity makes it shock sensitive and explosive in

water, so extra precautionary measures are needed to make sure that no accidents occur.

Additionally, the hydrogen gas produced by the reaction by the hydride with the solvent is

highly flammable.

Enantioselective reduction was very similar to the racemic reduction in that it involved

sodium borohydride as the reducing agent. However, the reaction was mediated by

(L)-tartaric acid in order to produce one specific enantiomer. This is advantageous over the

racemic reduction in that a specific enantiomer is produced over the other, providing greater

yield of the desired enantiomer. It also incorporates the advantages of the racemic reduction

reaction, including its relatively quick reaction time, compared to enzymatic reduction.

However, it requires the use of another enantiomeric compound to obtain mediate this

reaction, which could be hard or expensive to come by. Additionally, the chiral auxiliary will

be needed to be removed, and the reaction requires more steps and more specific

conditions (such as solvent) to perform, making it more complicated.