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Chemistry · Organic Chemistry

Organic Compounds Containing Nitrogen formulas for JEE

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

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ChemistryOrganic Compounds Containing Nitrogen1 / 20
QuestionState the formula — Basicity Constant of Amines
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Basicity Constant of AminesKb=[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
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All 20 Organic Compounds Containing Nitrogen formulas
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
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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