Consider all possible isomeric ketones, including stereoisomers of MW ...
Introduction:
In this question, we are given a set of isomeric ketones with a molecular weight of 100. We need to determine the number of ketones that will produce a racemic product when reacted with NaBH4.
Understanding the concept:
When a ketone is reacted with NaBH4, it undergoes reduction to form an alcohol. The reduction of a ketone by NaBH4 is a stereospecific process, meaning that the configuration of the product is determined by the configuration of the starting ketone.
Determining the number of ketones that give a racemic product:
To determine the number of ketones that give a racemic product, we need to consider the presence of a chiral center in the ketone molecule. A chiral center is a carbon atom bonded to four different groups.
Case 1: Ketones with no chiral centers:
If a ketone has no chiral centers, it will not produce a racemic product. This is because there is no possibility for the product to have different configurations.
Case 2: Ketones with one chiral center:
If a ketone has one chiral center, it can exist as a pair of enantiomers. When reacted with NaBH4, each enantiomer will produce the corresponding enantiomeric alcohol. Therefore, in this case, the ketone will give a racemic product.
Case 3: Ketones with two chiral centers:
If a ketone has two chiral centers, it can exist as a pair of diastereomers. When reacted with NaBH4, each diastereomer will produce a mixture of enantiomeric alcohols. Therefore, in this case, the ketone will give a racemic product.
Case 4: Ketones with more than two chiral centers:
If a ketone has more than two chiral centers, it can exist as a pair of diastereomers. However, in this case, the diastereomers will not be mirror images of each other, and the reaction with NaBH4 will not produce a racemic product.
Conclusion:
In summary, the ketones that give a racemic product when reacted with NaBH4 are those with one or two chiral centers. Therefore, out of all the possible isomeric ketones with a molecular weight of 100, there are 5 ketones that will produce a racemic product.
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