Chemistry · Organic Chemistry

Organic Compounds Containing Nitrogen formulas for JEE

Every Organic Compounds Containing Nitrogen formula you need for JEE, grouped by concept.

FormulasRevision notes
20 formulas3 concepts
01Amines02Amine Reactions03Diazonium Salts
01

Amines

2 formulas

Basicity Constant of Amines

Kb=[RNH3+][OH−][RNH2]K_b = \frac{[RNH_3^+][OH^-]}{[RNH_2]}

Equilibrium constant for the basic hydrolysis of an amine in aqueous solution.

applies whenAqueous solution.
aminesbasicityequilibrium

pKb of Amines

pKb=−log⁡10KbpK_b = -\log_{10} K_b

Logarithmic measure of the basic strength of an amine.

aminesbasicity
02

Amine Reactions

11 formulas

Aliphatic Amine with Nitrous Acid

R−NH2+HNO2→NaNO2+HCl[R−N2+Cl−]→H2OR−OH+N2↑+HClR-NH_2 + HNO_2 \xrightarrow{NaNO_2 + HCl} [R-N_2^+Cl^-] \xrightarrow{H_2O} R-OH + N_2\uparrow + HCl

Reaction of aliphatic primary amines yielding alcohols and evolving nitrogen quantitatively.

applies whenProduces unstable aliphatic diazonium intermediate.
aminesreactionsgas-evolution

Ammonolysis of Alkyl Halides

R−X+NH3→373KR−NH2+HXR-X + NH_3 \xrightarrow{373 K} R-NH_2 + HX

Nucleophilic substitution of alkyl halides by ammonia to form primary amines.

applies whenSealed tube at 373 K, ethanolic ammonia.
aminespreparationsubstitution

Bromination of Aniline

C6H5NH2+3Br2(aq)→2,4,6−tribromoaniline↓+3HBrC_6H_5NH_2 + 3Br_2(aq) \rightarrow 2,4,6-\text{tribromoaniline}\downarrow + 3HBr

Electrophilic substitution yielding a tribromo precipitate due to high activation.

applies whenAqueous bromine at room temperature.
amineselectrophilic-substitution

Carbylamine Reaction

R−NH2+CHCl3+3KOH→ΔR−NC+3KCl+3H2OR-NH_2 + CHCl_3 + 3KOH \xrightarrow{\Delta} R-NC + 3KCl + 3H_2O

Test for primary amines yielding a foul-smelling isocyanide.

applies whenHeating with ethanolic KOH; only for 1° aliphatic and aromatic amines.
aminesidentificationtestname-reaction

Gabriel Phthalimide Synthesis

Phthalimide→2.R−X,3.NaOH(aq)1.KOH(alc)R−NH2+Sodium phthalate\text{Phthalimide} \xrightarrow[2. R-X, 3. NaOH(aq)]{1. KOH(alc)} R-NH_2 + \text{Sodium phthalate}

Preparation of purely aliphatic primary amines from phthalimide.

applies whenOnly applicable for aliphatic primary amines.
aminespreparationname-reaction

Hinsberg's Test (1° Amine)

C6H5SO2Cl+R−NH2→C6H5SO2NHR+HClC_6H_5SO_2Cl + R-NH_2 \rightarrow C_6H_5SO_2NHR + HCl

Reaction of primary amine with benzenesulphonyl chloride forming an alkali-soluble sulphonamide.

applies whenProduct is soluble in alkali due to acidic N-H proton.
aminesidentificationtest

Hinsberg's Test (2° Amine)

C6H5SO2Cl+R2NH→C6H5SO2NR2+HClC_6H_5SO_2Cl + R_2NH \rightarrow C_6H_5SO_2NR_2 + HCl

Reaction of secondary amine with benzenesulphonyl chloride forming an alkali-insoluble sulphonamide.

applies whenProduct is insoluble in alkali.
aminesidentificationtest

Hoffmann Bromamide Degradation

R−CONH2+Br2+4NaOH→R−NH2+Na2CO3+2NaBr+2H2OR-CONH_2 + Br_2 + 4NaOH \rightarrow R-NH_2 + Na_2CO_3 + 2NaBr + 2H_2O

Conversion of an amide to a primary amine with one fewer carbon atom.

applies whenAqueous or ethanolic NaOH.
aminespreparationstep-downname-reaction

Libermann Nitroso Test

R2NH+HNO2→R2N−N=O+H2OR_2NH + HNO_2 \rightarrow R_2N-N=O + H_2O

Reaction of secondary amines with nitrous acid forming N-nitrosamines.

applies whenForms a yellow oily liquid.
aminestestnitrous-acidjee-advanced

Hoffmann Mustard Oil Reaction

R−NH2+CS2→HgCl2R−N=C=S+HgS↓+2HClR-NH_2 + CS_2 \xrightarrow{HgCl_2} R-N=C=S + HgS\downarrow + 2HCl

Test for primary amines producing a pungent alkyl isothiocyanate.

applies whenHeating with CS2 followed by addition of HgCl2.
aminestestname-reactionjee-advanced

Sulphonation of Aniline

C6H5NH2→H2SO4(conc.)C6H5N+H3HSO4−→453−473 Kp−H3N+C6H4SO3−C_6H_5NH_2 \xrightarrow{H_2SO_4(conc.)} C_6H_5N^+H_3HSO_4^- \xrightarrow{453-473\,K} p-H_3N^+C_6H_4SO_3^-

Formation of sulphanilic acid, which exists as a zwitterion.

applies whenHeating at 453-473 K.
amineselectrophilic-substitutionzwitterion
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03

Diazonium Salts

7 formulas

Diazotisation of Aniline

C6H5NH2+NaNO2+2HCl→273−278 KC6H5N2+Cl−+NaCl+2H2OC_6H_5NH_2 + NaNO_2 + 2HCl \xrightarrow{273-278\,K} C_6H_5N_2^+Cl^- + NaCl + 2H_2O

Conversion of primary aromatic amine to diazonium salt.

applies whenLow temperature (273-278 K).
aminesdiazoniumpreparation

Azo Coupling Reaction

Ar−N2+Cl−+C6H5OH→OH−Ar−N=N−C6H4OH+Cl−Ar-N_2^+Cl^- + C_6H_5OH \xrightarrow{OH^-} Ar-N=N-C_6H_4OH + Cl^-

Electrophilic aromatic substitution of a phenol or aniline by a diazonium ion to form an azo dye.

applies whenBasic medium for phenol (pH 9-10), weakly acidic for aniline (pH 4-5).
diazoniumcouplingdye

Balz-Schiemann Reaction

Ar−N2+Cl−+HBF4→Ar−N2+BF4−→ΔAr−F+BF3+N2↑Ar-N_2^+Cl^- + HBF_4 \rightarrow Ar-N_2^+BF_4^- \xrightarrow{\Delta} Ar-F + BF_3 + N_2\uparrow

Preparation of aryl fluorides from diazonium fluoroborates.

applies whenHeating the isolated fluoroborate salt.
diazoniumfluorinationname-reaction

Reduction of Diazonium with Ethanol

Ar−N2+Cl−+CH3CH2OH→Ar−H+N2↑+CH3CHO+HClAr-N_2^+Cl^- + CH_3CH_2OH \rightarrow Ar-H + N_2\uparrow + CH_3CHO + HCl

Reduction of diazonium salts to arenes by ethanol.

diazoniumreduction

Reduction of Diazonium with Hypophosphorous Acid

Ar−N2+Cl−+H3PO2+H2O→Ar−H+N2↑+H3PO3+HClAr-N_2^+Cl^- + H_3PO_2 + H_2O \rightarrow Ar-H + N_2\uparrow + H_3PO_3 + HCl

Mild reduction of diazonium salts to arenes by hypophosphorous acid.

applies whenAqueous medium.
diazoniumreduction

Gattermann Reaction

Ar−N2+Cl−→Cu/HXAr−X+N2↑Ar-N_2^+Cl^- \xrightarrow{Cu/HX} Ar-X + N_2\uparrow

Replacement of diazonium group by halogens using copper powder.

applies whenX = Cl, Br; requires finely divided copper powder.
diazoniumsubstitutionname-reaction

Sandmeyer Reaction

Ar−N2+Cl−→CuX/HXAr−X+N2↑Ar-N_2^+Cl^- \xrightarrow{CuX/HX} Ar-X + N_2\uparrow

Replacement of diazonium group by Cl, Br, or CN using Cu(I) salts.

applies whenX = Cl, Br, CN; requires Cu(I) salt catalyst.
diazoniumsubstitutionname-reaction
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