CHAPTER 5: Question 1

2D explanations

Any compound which possesses a stereocentre adjacent to a carbon-oxygen double bond, and has a hydrogen atom as one of the substituents on the stereocentre will racemize when treated with base. If the carbon-oxygen double bond is an aldehyde or ketone, then the compound will also racemize when treated with acid. This is shown schematically below. Hence:

A This compound contains a stereocentre adjacent to the carbon-oxygen double bond of an ester, and one of the substituents on the stereocentre is a hydrogen atom. Thus the compound will racemize under basic conditions.

B  This compound contains a stereocentre adjacent to the carbon-oxygen double bond of an ester, but there is no hydrogen atom attached to the stereocentre. Thus the compound will not racemize under acidic or basic conditions.

C This compound contains a stereocentre adjacent to the carbon-oxygen double bond of a ketone, and one of the substituents on the stereocentre is a hydrogen atom. Thus the compound will racemize under acidic and basic conditions.

D This compound contains a stereocentre adjacent to the carbon-oxygen double bond of an aldehyde, and one of the substituents on the stereocentre is a hydrogen atom. Thus the compound will racemize under acidic and basic conditions.

E  This compound contains a stereocentre adjacent to the carbon-oxygen double bond of an aldehyde, but there is no hydrogen atom attached to the stereocentre. Thus the compound will not racemize under acidic or basic conditions.

F This compound contains a stereocentre adjacent to the carbon-oxygen double bond of both a ketone and an ester, and one of the substituents on the stereocentre is a hydrogen atom. Thus the compound will racemize under acidic and basic conditions.

 
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