Reactions of Simple Aliphatic Amines
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry and stereochemistry of the reaction.Click the mouse on the reactant molecule to view the answer;
click on the reagent to briefly review the reaction.
Acid halides undergo nucleophilic attack by azide anion, N3-, to give unsatble acyl azides. On heating, the acyl azide will decompose (the Curtius rearrangement) to form the aliphatic amine, CO2 and N2.
Primary amines react with p-toluenesulfonyl chloride to form primary sulfonamides. The primary sulfonamide is base-soluble (the NH proton is acidic), forming the basis of the Hinsberg Test.
Pthalimide anion is a strong nucleophile and will reack with alkyl halides to give N-substituted imides. On hydrolysis, this yield the corresponding primary amine and pthalic acid.
Simple amines are good nucleophiles and will react with alkyl halides to yield substitution products by an SN2 mechanism.
Acid halides undergo nucleophilic attack by azide anion, N3-, to give unsatble acyl azides. On heating, the acyl azide will decompose (the Curtius rearrangement) to form the aliphatic amine, CO2 and N2.
Primary amines react with p-toluenesulfonyl chloride to form primary sulfonamides. The primary sulfonamide is base-soluble (the NH proton is acidic), forming the basis of the Hinsberg Test.
Pthalimide anion is a strong nucleophile and will reack with alkyl halides to give N-substituted imides. On hydrolysis, this yield the corresponding primary amine and pthalic acid.
Simple amines are good nucleophiles and will react with alkyl halides to yield substitution products by an SN2 mechanism.