Tutorial%203A - CHEM 281 Tutorial Problem Set No 3 1 In...

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CHEM 281 Tutorial Problem Set No. 3 1. In class we learned that although chiral molecules share many of the same physical properties, their interactions with plane-polarized light are unique. Below are two examples of chiral molecules whose enantiomers demonstrate additional unique or detrimental properties. a) please draw a chemical structure for both enantiomers of thalidomide and point out which enantiomer is ( R ) and which is ( S ). Also, describe how a lack of appreciation for the unique properties of enantiomers led to serious side effects when this molecule was used as a racemic drug. Roughly, what percentage of current drugs on the market are chiral? Thalidomide is a sedative, hypnotic, and anti-inflammatory medication that was sold from 1957 to 1961 in almost fifty countries. Thalidomide was chiefly sold and prescribed during this time to pregnant women to combat morning sickness and as an aid to help them sleep. Unfortunately, inadequate tests were performed to assess the drug's safety, with catastrophic results for the children of women who had taken thalidomide during their pregnancies. As a result, approximately 10,000 children were born with severe malformities, because their mothers had taken thalidomide during pregnancy. In 1962, in reaction to the tragedy, many countries enacted laws requiring tests for safety during pregnancy before a drug can receive approval for sale. Thalidomide is racemic – it contains both (R) and (S) enantiomers in equal
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Tutorial%203A - CHEM 281 Tutorial Problem Set No 3 1 In...

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