Question

Write reactions of the final alkylation product of aniline with excess of methyl iodide in the presence of sodium carbonate solution.

Answer 1

\[\ce{\underset{Aniline}{C6H5\overset{\bullet\bullet}{N}H2} + CH3 - I -> \underset{N-Methylanilinium iodide}{[C6H5\overset{+}{N}H2CH3]I^-}}\]

\[\ce{2[C6H5\overset{+}{N}H2CH3]I- + Na2CO3 -> \underset{N-Methylaniline}{2C6H5NHCH3} + CO2 + 2NaI}\]

\[\ce{C6H5\overset{\bullet\bullet}{N}HCH3 ->[+ CH3I][Na2CO3] \underset{N, N-Dimethylaniline}{C6H5N(CH3)2}}\]

\[\ce{C6H5\overset{\bullet\bullet}{N}(CH3)2 + CH3 - I -> \underset{N, N, N-Trimethylanilinium iodide}{[C6H5\overset{+}{N}(CH3)3]I^-}}\]

\[\ce{2C6H5\overset{+}{N}(CH3)3I- + Na2CO3 -> \underset{N, N, N-Trimethylanilinium carbonate}{[C6H5\overset{+}{N}(CH3)3]2CO^{2-}3} + 2NaI}\]