I found a question to determine the number of possible chiral products of monochlorination of 2-chloropentane.So, first the products are (with possible number of enantiomers in the parentheses:
2,2-dichloropentane(no chiral product),
1,2-dichloropentane(4 or 2, I am not sure is there a plane of symmetry here)
2,3-dichloropentane(2 or 4)
2,4-dichloropentane(obviously none for a plane of symmetry)
2,5-dichloropentane(2,4?)
But my surprisingly the answer says it's only 5. That's even lower than my lower estimate. I am not sure how there are 5 enantiomers.
Answer
2-chloropentane is optically active compound hence in some cases we will get only diastereomers. For example 1,2-dichloropentane is single product because it is formed by attack at carbon no. 1 hence no change in chirality of carbon no. 2. So product formed by attack at carbon 1 (one chiral product) carbon3 (two chiral product i.e. diastereomers) carbon 4 (one chiral product, i.e. one chiral and one meso) carbon5 (one chiral product)
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