Iodide ion reacts with chloromethane to displace chlorideion in a common organic substitution reaction: I⁻+CH3Cl →CH3I+Cl⁻ (a) Draw a wedge-bond structure of chloroform and indicatethe most effective direction of Iattack.(b) The analogous reaction with 2-chlorobutane [FigureP16.107(b)] results in a major change in specific rotation asmeasured by polarimetry. Explain, showing a wedge-bondstructure of the product.(c) Under different conditions, 2-chlorobutane loses Clin arate-determining step to form a planar intermediate [FigureP16.107(c)]. This cationic species reacts with HI and then losesHto form a product that exhibits no optical activity. Explain,showing a wedge-bond structure.
Iodide ion reacts with chloromethane to displace chlorideion in a common organic substitution reaction: I⁻+CH3Cl →CH3I+Cl⁻ (a) Draw a wedge-bond structure of chloroform and indicatethe most effective direction of Iattack.(b) The analogous reaction with 2-chlorobutane [FigureP16.107(b)] results in a major change in specific rotation asmeasured by polarimetry. Explain, showing a wedge-bondstructure of the product.(c) Under different conditions, 2-chlorobutane loses Clin arate-determining step to form a planar intermediate [FigureP16.107(c)]. This cationic species reacts with HI and then losesHto form a product that exhibits no optical activity. Explain,showing a wedge-bond structure.
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