Monochlorination of 2-chloropentane and possible enantiomer products
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)