Iodide ion reacts with chloromethane to displace chloride ion in a common organic substitution reaction:
(a) Draw a wedge-bond structure of chloroform and indicate the most effective direction of attack.
(b) The analogous reaction with 2-chlorobutane [Figure P16.107(b)] results in a major change in specific rotation as measured by polarimetry. Explain, showing a wedge-bond structure of the product.
(c) Under different conditions, 2-chlorobutane loses in a rate-determining step to form a planar intermediate [Figure P16.107(c)]. This cationic species reacts with HI and then loses H to form a product that exhibits no optical activity. Explain, showing a wedge-bond structure.
