Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the major product B in the following reaction sequence:
Correct answer
1
Step-by-step solution
The starting material, 4-bromocyclohexylmethanamine, contains both a nucleophilic primary amine group and an electrophilic secondary bromide. In the presence of dilute OH^- , the amine nitrogen undergoes an intramolecular S_N2 reaction, attacking the C4 carbon and displacing the bromide ion. This cyclization forms the bicyclic intermediate A, 2-azabicyclo[2.2.2]octane. Treatment of intermediate A with excess CH₃I results in exhaustive methylation, converting the amine into a quaternary ammonium iodide salt. Subsequ