Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the major product of the following reaction.
Correct answer
2
Step-by-step solution
The given reaction involves a secondary alkyl halide reacting with sodium hydrosulfide ( NaSH ). NaSH provides the SH ⁻ ion, which is a strong nucleophile. The reaction proceeds via an S _ N 2 mechanism. Iodine ( I ⁻ ) is an excellent leaving group, whereas - OH and - OMe are poor leaving groups. Therefore, nucleophilic substitution occurs exclusively at the carbon atom bonded to iodine. An S _ N 2 reaction proceeds with complete inversion of configuration at the reacting center. Since the iodine atom is on a dashe