Answer: A, B, D
3-Methylpentane has four sets of equivalent hydrogens (the two ethyl CH3, the two CH2, the tertiary CH, and the methyl on C-3), so four constitutional monochlorides arise. Of these only 1-chloro-3-methylpentane (one stereocentre) and 2-chloro-3-methylpentane (two stereocentres) are chiral, giving 2 + 4 + 1 + 1 = 8 stereoisomers. Three chiral constitutional isomers is wrong (two), and the tertiary-hydrogen product, 3-chloro-3-methylpentane, is achiral. RDKit confirms 4 and 8.