JEE Advanced levelSingle correct optionDifficulty 3 of 3el196
Which pair of reagents would give cetyltrimethylammonium bromide, [CX16HX33N(CHX3)X3]X+BrX−, directly in one step?
ACX16HX33OH and (CHX3)X3N
B(CHX3)X3N and CX16HX33Br
CCX15HX31COOH and (CHX3)X3N
DCX16HX33NHX2 and one equivalent of CHX3Br
Answer: B
Trimethylamine is a nucleophile that attacks the primary alkyl bromide in an SN2 reaction: (CHX3)X3N+CX16HX33Br[CX16HX33N(CHX3)X3]X+BrX−. One equivalent of CHX3Br with a primary amine gives a mixture of lower alkylation products, and alcohols or acids do not alkylate the amine.