IIT JEE Advanced 2006 Paper 1

The possible isomeric products (N) formed from the reaction are

Thus, a total of 2 + 2 + 1 + 1= 6 isomers are formed.
Since d, l isomers cannot be separated on fractional distillation, so the isomers (M) are four:
H3C−

CH2Cl |

C

−CH2CH3 +

CH3 |

HC

| CH3

−

Cl |

CH

−CH3 + H3C−

CH3 |

C

| H

−CH2CH2Cl + H3C−

CH3 |

C

| CH3

−CH2CH3