VJC 2025 Organic Compounds Tutorial

1 Victoria Junior College Organic Chemistry Tutorial: Nitrogen Compounds [H2 Only] SELF-CHECK EXERCISE a) Complete the following tables. Reactant Reaction Type, Reagents & Conditions Intermediate Reaction Type, Reagents & Conditions Products Nucleophilic substitution excess NH3, heat in a sealed tube CH3CH2NH2 ethylamine Nucleophilic substitution CH3CH2Cl, heat Condensation CH3COCl Reduction  LiA lH4 in dry ether Neutralisation HCl Neutralisation RCO2H Reduction  H 2, Ni catalyst, heat  H 2, Pt catalyst  LiA lH4 in dry ether Reactant Reaction Type, Reagents & Conditions Intermediate Reaction Type, Reagents & Conditions Products Reduction Sn and concentrated HCl, heat then add alkali such as NaOH(aq) phenylamine Nucleophilic substitution CH3CH2Cl, heat Condensation CH3COCl Neutralisation HCl Electrophilic substitution Br2(aq)

2 Reactant Reaction Type, Reagents & Conditions Intermediate Reaction Type, Reagents & Conditions Products Nucleophilic substitution Concentrated NH3 CH3CONH2 ethanamide Acid hydrolysis HCl(aq), heat Base hydrolysis NaOH(aq), heat Reduction LiAlH4 in dry ether b) Write down the organic compounds in the following mind map. OH―(aq) OH―(aq) heat NH3 Concentrated NH3 CH3CONH2 H+(aq), heat LiAlH4 in dy ether NH3(alc), heat H+(aq) NH3(alc) heat, excess CH 3CH2Cl CH3COCl OH―(aq)

3 c) Tick the functional groups that would be reduced. Reducing agents Alkene RCHO RCOR RCO 2H RCONH 2 RCN Nitrobenzene LiAlH4 in dry ether H2, Pt NaBH4 in methanol Sn in concentrated HCl, heat, followed by NaOH d) State the type of reactions that would occur. Reagents & conditions Alkene RX 1o or 2o ROH RCHO RCOR RCO 2H RCONH2 RCN RCOCl KMnO4, H2SO4(aq), heat K2Cr2O7, H2SO4(aq), heat OH▬(aq), heat H2O Relative basicities of amines Recall: Based on availability of lone pair of electrons on N (as Lewis base)  Basic strength increases when the lone pair of electrons on N is more available for donation to an acid.  Factors that affect availability of lone electron pair on N: - Inductive effect - Delocalisation (resonance effect) - Steric hindrance – block acid from approaching the N atom

4 1 (a) Suggest and explain the relative basicities of methylamine and ethylamine in gaseous state in terms of Lewis bases. ……………………………………………………………………………………………………… ……………………………………………………………………………………………………… ……………………………………………………………………………………………………… ……………………………………………………………………………………………………… ……………………………………………………………………………………………………… ……………………………………………………………………………………………………[3] (b) Explain in terms of structures why ammonia is