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H2 Chemistry Organic Chemistry - Reactions

Reactions/ Hydrocarbons

Alkanes –C–C–
Combustion For all hydrocarbons

Alkenes C=C

Arenes – Benzene

Arenes – Methylbenzene CH3

Combustion Hydrogenation Nitration

Hydrogenation Reagent: H2(g) Condition: 150oC + Ni catalyst or Pt catalyst + r.t. Product: Alkanes *Useful in analysing no. of C=C by measuring amt. of hydrogen absorbed by 1 mol of hydrocarbon Reagent: Br2 in CCl4 Condition: r.t., NO UV light Product: Dibromoalkane Observation: Reddishbrown colour of Br2 is rapidly decolourised * Test for unsaturation

Nitration Reagent: mixture of conc. HNO3 Condition: & conc. H2SO4 + reflux at ≤ 60oC Product: Nitrobenzene

Nitration Reagent: mixture of conc. HNO3 Condition: & conc. H2SO4 + 30oC *If temperature is high, further substitution may occur * Methylbenzene more reactive Of side-chain Reagent: Cl2(g) bubbled into boiling methylbenzene Condition: Sunlight/UV light Reagent: Cl2(g) / Br2(l) Condition: halogen-carrier (w/o sunlight)

Halogenation

Reagent: Cl2 (or Br2) in CCl4 Condition: UV light/sunlight Product: Chloroalkanes/ Bromoalkanes

Reagent: Cl2(g) / Br2(l) Condition: halogencarriers + r.t. Product:

1 R = alkyl/aryl groupX = halogen (F, Cl, Br or I)

acidified manganate (VII)ions Condition: heat + H+/MnO42 R = alkyl/aryl groupX = halogen (F.Reactions Hydration Industrial Reagent: H2O(g) Condition: H3PO4 catalyst + 300oC + 70 atm Product: Alcohols Laboratory Reagent: conc.H2 Chemistry Organic Chemistry . alkaline manganate(VII) ions Condition: OH-/MnO4Product: diols Observation: Purple colour of MnO4.t. Oxidation By hot.is discharged & brown manganese(IV) oxide is formed *Test for unsaturation Of side-chain Reagent: H+/MnO4Condition: reflux Product: Carboxylic acid Observations: Decolourisation of purple acidified KMnO4 solution. H2SO4 + H2O Condition: Product: Alcohols Hydrohalogenation Reagent: HX Condition: r. Cl. Product: Halogenoalkanes Mild Oxidation by cold. White ppt of benzoic acid *Test to distinguish benzene & methylbenzene * For alkylbenzenes with longer alkyl chains. products include CO2 and H2O too. Br or I) . dilute.

t.Alcohols – Phenols O H Hydrolysis Nitration Hydrolysis Reagent: KOH(aq) / NaOH(aq) Condition: reflux Product: Alcohols Nitration of benzene ring Reagent: HNO3 (aq) Condition: r. Br or I) .t. Reagent: Mixture of conc.H2 Chemistry Organic Chemistry . 3 R = alkyl/aryl groupX = halogen (F.Reactions Product: Carboxylic acids & Ketones By ozone Reagent: Condition: Product: Carbonyl compounds (aldehydes & ketones) Polymerisation Reagent: Condition: Product: Poly(alkenes) Others Friedel-Crafts Reaction Reagent: RX Condition: reflux + AlCl3 Product: Halogenoarenes Reactions/ Hydrocarbons Halogenoalkanes Hydroxy Compounds Hydroxy Compounds Carboxylic Acids . H2SO4 & HNO3 Condition: r. Cl.

H2 Chemistry Organic Chemistry . white ppt formed & HBr fumes liberated *Chemical test for phenol Reagent: X2 in CCl4 [mono] Condition: r. H2SO4 **Involves breakage of C-O bond Of benzene ring Reagent: X2 (aq) [tri] Condition: r.t. 4Observation: Reddish brown Br is decolourised & HBr fumes liberated Halogenation Substitution with PX3 Reagent: PX3 Product: R – X + H3PO3 Substitution with SOCl2 Reagent: SOCl2 (thionyl chloride) Product: R – Cl + SO2 + HCl (g) Substitution with PCl5 Reagent: PCl5 Product: R – Cl + POCl3 + HCl (g) Observations: White fumes of HCl evolved *Test for alcohol Reaction with PCl5 Reagent: PCl5 *No reaction *Breakage of C – O bond is very difficult because the p orbital of Oxygen atom overlaps with π cloud of benzene ring 4 R = alkyl/aryl groupX = halogen (F.Reactions Halogenation Substitution with HX Reagent: HX (g)* Condition: Reflux Product: R – X + H2O *Prepared in situ by mixing NaX or KX with conc. Product: tri-bromine Observations: Reddish brown Br is decolourised. Product: mixture of 2-. Cl. Br or I) .t.

) Product: Alkenes* *Major product = more substituted alkene = more alkyl group Of Esters Reagent: Alcohol + carboxylic acid Condition: conc. conc. H2SO4 / Al2O3 Condition: 170oC / 360oC (resp. Br or I) .H2 Chemistry Organic Chemistry .Reactions Hydration Deyhydration To Corresponding Alkene Reagent: Excess conc. Using excess alcohol 2. carbonates & metals Product: Salts *Vigorous evolution of CO2 with Na2CO3 shows that carboxylic acids are stronger acids than phenol 5 R = alkyl/aryl groupX = halogen (F. H2SO4 serves to remove water formed Formation Formation Of nitriles/cyanides Reagent: alcoholic KCN/NaCN Condition: reflux Product: nitriles/cyanides *Used to lengthen carbon chain Of Salts Reagent: Bases. H2SO4 Product: Esters * Breakage of O-H bond is slow & reversible *Suitable for preparing aliphatic esters *Better yield of ester achieved by: 1. Cl. Removal of ester as it is formed 3.

Product: Esters *Better ‘cos able to carry out in r.t. H2SO4 removes the H2O formed. Mild Oxidation Reagent: Acidified K2Cr2O7 Condition: Distil Product: Aldehydes Observations: Orange Cr2O72. ammonia Oxidation Oxidation 6 R = alkyl/aryl groupX = halogen (F.Reactions Acylation Reagent: Alcohol + acyl chloride Condition: r.turned to green Cr3+ *Further heating with excess H+/ K2Cr2O7 further oxidises aldehyde to carboxylic acids Of amines Reagent: conc. / warm (resp. which can escape easily from solution 1o Alcohols. use excess conc.H2 Chemistry Organic Chemistry . H2SO4 Product: Esters + H2O *Conc.) Product: Acyl chlorides *Use of SOCl2 is preferred ‘cos both SO2 & HCl are gases. hence increase the yield of ester by shifting the position of equilibrium to the right *Involves braking C – O of carboxyl group & O – H in alcohol Of Acyl Chlorides Reagent: PCl5 / SOCl2 Condition: r. *Acyl chloride is very reactive thus faster reaction Acylation Reagent: acyl chloride Product: Esters + HCl Reagent: alkaline phenol + benzoyl chloride Product: Esters Of Esters Reagent: Alcohols Condition: reflux + conc. NH3 (in ethanol) Condition: heat in sealed tube Product: Amines *For higher yield of 1o amine. Cl.t. Br or I) .t.

H2 Chemistry Organic Chemistry . Strong Oxidation Reagent: Acidified K2Cr2O7/ Acidified KMnO4 Condition: Reflux Product: Carboxylic acids Observations: Orange Cr2O72.turned to green Cr3+ / Purple KMnO4 is decolourised **3o Alcohols resistant to oxidation Elimination Of -HX Reagent: alcoholic KOH or ethanolic KOH/NaOH Condition: Reflux Product: Alkenes 7 R = alkyl/aryl groupX = halogen (F.Reactions 1o Alcohols. Cl. Br or I) .turned to green Cr3+ / Purple KMnO4 is decolourised 2o Alcohols. Strong Oxidation Reagent: Acidified K2Cr2O7/ Acidified KMnO4 Condition: Reflux Product: Ketones Observations: Orange Cr2O72.

5] (for Carbonyl Cmpds) – [3. 4. Br or I) . Cl. 5. 3. 6. 3] 8 R = alkyl/aryl groupX = halogen (F.Reactions Others Reaction with Na/Reactive Metal Reagent: Na / reactive metal Product: H2 + alkoxide (R – O-) Observation: sodium sinks & bubbles of H2(g) evolved *Reactivity of alcohols with Na decreases as acid strength decreases from primary to tertiary alcohols Iodoform Test Reagent: I2 (aq) / NaOH (aq) Condition: Warm Observations: Yellow ppt/crystal with an “antiseptic” smell Reaction with Reactive Metal Reagent: Reactive metal Product: H2 gas + phenoxide salt Observation: Sodium sinks & bubbles of H2(g) evolved *Reaction is more vigorous than with ethanol ‘cos phenol is a stronger acid than ethanol Reaction with Base Reagent: NaOH Product: salt + water *Alcohols do not react with base as breakage of O – H bond in phenol is easier than in alcohol as phenol is a stronger acid Reaction with Sodium Carbonate Reagent: Na2CO3 *No reaction *Used to distinguish phenol from carboxylic acid Others Equation: (for Alcohol) – [4.H2 Chemistry Organic Chemistry .

Br or I) .4-dinitrophenylhydrazine (Brady’s reagent) presence of carbonyl compounds Condition: Warm Observation: orange ppt (NOT YELLOW) Equations: [Aldehyde] Carbonyl Compounds – Ketones R’/R C=O R *Used to detect Brady’s reagent [Ketone] 9 R = alkyl/aryl groupX = halogen (F.Reactions *To identify organic compound with the following structural units Reactions/ Hydrocarbons Carbonyl Compounds – Aldehydes H/C C=O H Reagent: 2. Cl.H2 Chemistry Organic Chemistry .

Br or I) .H2 Chemistry Organic Chemistry . Cl.Reactions Reagent: I2 (aq) & NaOH (aq) Iodoform test compounds with: Condition: Warm Observations: Yellow ppt/crystal of CHI3 with an “antiseptic” smell Equations: [Aldehyde] *Used to detect carbonyl [Ketone] Reduction Reagent: LiAlH4 Condition: In dry ether Equations: [Aldehyde] [Ketone] Formation Of cyanohydrin (‘Step-up’ reaction) Reagent: HCN Condition: Trace amt of NaOH (or NaCN) Product: Hydroxynitrile (aka cyanohydrin) Equations: [Aldehyde] 10 R = alkyl/aryl groupX = halogen (F.

turns green Product: Carboxylic acids Tollens’ reagent (test for all aldehydes) Reagent: Ag(NH3)2+ (colourless) Observation: Aldehydes give a grey ppt of Ag(s) or ‘silver mirror’ *Ketones have no reaction Fehling’s solution (only for aliphatic aldehydes) Reagent: Alkaline soln of complex copper(II) ions – deep blue soln Observation: Aldehydes give a red ppt of Cu2O *Benzaldehyde & ketones have no reaction Acidified aq K2Cr2O7 (for all aldehydes) Condition: Reflux Observation: Orange acidified K2Cr2O7 turns green Acidified aqueous KMnO4 (for all aldehydes) Condition: Reflux Observation: Purple acidified KMnO4 is decolourised 11 Differentiating Tests R = alkyl/aryl groupX = halogen (F.Reactions [Ketone] Oxidation Reagent: K2Cr2O7/H+ Condition: Warm Observation: Orange Cr2O72. Cl. Br or I) .H2 Chemistry Organic Chemistry .

H2 Chemistry Organic Chemistry . Cl. Br or I) .Reactions 12 R = alkyl/aryl groupX = halogen (F.