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)
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.