Organic Chem Reactions

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Organic Chem Reactions

1. Alkanes

a. Reactions  Combustion  Free-radical substitution o Steps  Initiation  Propagation  Termination o Conditions  Cl2(g)/Br2(l), UV light b. Formation  Hydrogenation of Alkenes

o H2(g) with Nickel catalyst, at ~150oC, ~5atm

o H2(g) with Pt or Pd catalyst, at room temperature

 Decarboxylation of sodium salt of carboxylic acid o Heating with sodalime

2. Alkenes

a. Reactions

 Addition of bromine

o Br2(l) / Br2 dissolved in CCl4, room temperature

 Addition of bromine water

o Bromine water at room temperature  Addition of HBr

o HBr(g)/ HBr dissolved in CCl4, room temperature

 Direct hydration

o Steam, H3PO4 catalyst, 300oC, 65 atm

 Indirect hydration

o Cold concentrated H2SO4, followed by heating in the presence of

water

 Addition of Hydrogen

o H2(g) with Nickel catalyst, at ~150oC, ~5atm

o H2(g) with Pt or Pd catalyst, at room temperature

 Oxidation

o Partial bond cleavage

 Cold alkali/ cold, dilute acidified KMnO4

o Total bond cleavage

 Hot, acidified KMnO4

 Combustion b. Formation  Dehydration of Alcohols o Excess, concentrated H2SO4, 180oC o Al2O3, 400oC  Dehydrohalogenation of halogenoalkane

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o Alcoholic KOH, relfux

3. Benzene

a. Reactions  Nitration

o Concentrated HNO3, concentrated H2SO4, reflux at less than 60oC

 Halogenation

o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

 Friedel-Crafts Alkylation

o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

 Friedel-Crafts Acylation

o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

4. Alkylbenzene

a. Reactions (side-chain)  Halogenation

o Cl2(g)/Br2(l), UV light

 Oxidation

o Alkaline/ acidified KMnO4, reflux

o Entire side chain is oxidized into CO2H

b. Formation

 Friedel-Crafts Alkylation

o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

5. Alcohols

a. Reactions

 Esterification

o Concentrated H2SO4, reflux

 Acylation

 Halogenation (hydrogen halide)

o NaCl(s), concentrated H2SO4, reflux

o HX, reflux

 Halogenation (phosphorus halide) o Cold PCl5

o Red P and Br2, reflux

o Red P and I2, reflux

 Halogenation (Sulfur dichloride oxide) o SOCl2, dissolved in pyridine

 Dehydration

o Excess, concentrated H2SO4, 180oC

o Al2O3, 400oC

 Formation of alkyl hydrogensulfate

o Concentrated H2SO4, reflux at 80oC

 Combustion  Oxidation

o For aldehyde

 Acidified K2Cr2O7, heat to distill

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 Acidified K2Cr2O7/ KMnO4, reflux

b. Formation

 Alkaline hydrolysis of halogenoalkane o Aqueous KOH, reflux

 Direct hydration of alkenes

o Steam, H3PO4 catalyst, 300oC, 65 atm

 Indirect hydration of alkenes

o Cold concentrated H2SO4, followed by heating in the presence of

water

 Reduction of carbonyl compounds o H2(g) with Ni catalyst at 140oC

o LiAlH4, dissolved in dry ether at room temperature

c. Test

 Tri-iodomethane/ Iodoform test o Alkaline I2(aq), heat

o Solid I2, NaOH(aq), heat

o NaOI(l), heat

6. Phenol

a. Reactions

 Esterification

o Acid chloride and NaOH(aq)  Halogenation

o Br2 dissolved in CCl4

o Chlorine/ Bromine water at room temperature  Nitration

o Dilute HNO3, room temperature

b. Test

 Neutral Iron(III) chloride solution at room temperature o Violet coloration

 Bromine water at room temperature

o Decolourisation and white precipitate

7. Aliphatic carbonyl compounds

a. Reactions

 Oxidation of aldehydes

o Acidified K2Cr2O7/ KMnO4, heat

o Alkaline KMnO4, heat

o Tollen’s Reagent, heat

 Ammoniacal silver(I) nitrate o Fehling’s Solution, heat

 Alkaline copper(II) tartrate  Reduction

o H2(g) with Ni catalyst at 140oC

o LiAlH4, dissolved in dry ether at room temperature

 Addition of HCN

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o HCN (aq), small amount of KCN, 10-20o

C  Condensation reaction with Brady’s Reagent

o Brady’s Reagent, room temperature. b. Test

 Tri-iodomethane test o Alkaline I2(aq), heat

o Solid I2, NaOH(aq), heat

o NaOI(l), heat c. Formation

 Oxidation of alcohols

o Acidified K2Cr2O7/ KMnO4, heat (to distill for aldehyde)

8. Aromatic carbonyl compounds

a. Reactions

 Oxidation of aldehydes o Acidified KMnO4, heat

o Alkaline KMnO4, heat

o Tollen’s Reagent, heat

 Ammoniacal silver(I) nitrate o NOT Fehling’s solution

 Reduction

o LiAlH4, dissolved in dry ether at room temperature

 Condensation reaction with Brady’s Reagent o Brady’s Reagent, room temperature.  Electrophilic substitution of benzene ring

o Fuming HNO, concentrated H2SO4, reflux at 40oC

o Cl2 , anhydrous FeCl3, at room temperature

b. Test

 Tri-iodomethane test o Alkaline I2(aq), heat

o Solid I2, NaOH(aq), heat

o NaOI(l), heat c. Formation

 For benzaldehyde

o Excess Cl2 gas and UV light, followed by reflux with NaOH (aq)

 For phenylethanone

o CH3COCl with anhydrous AlCl3 catalyst, 40oC

9. Carboxylic acid

a. Reactions

 Metal, metal carbonate, alkali o Room temperature

 Formation of acyl chloride by a halogen atom o PCl5(s), cold

o PCl3(l), cold

o SOCl2, dissolved in pyridine

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o Concentrated H2SO4, reflux

 Reductions

o LiAlH4, dry ether, room temperature

b. Formation

 Oxidation of primary alcohol

o Acidified K2Cr2O7/ KMnO4, reflux

 Oxidation of aldehydes

o Acidified K2Cr2O7/ KMnO4, reflux

 Oxidation of methyl benzene o Acidified KMnO4, heat

o Alkaline KMnO4, heat

 Acid hydrolysis of nitriles o Dilute HCl, reflux  Alkali hydrolysis of nitriles

o Dilute NaOH, reflux, followed by acidify

10. Carboxylic acid derivatives

a. Reactions

 Hydrolysis o Ester

 Dilute H2SO4, reflux

o Acyl chloride

 Water, room temperature o Amide

 Dilute HCl, reflux  React with alcohol/ phenol

o Acyl chloride  Room temperature  Reaction with NH3 o Ester  Concentrated alcoholic NH3 o Acyl chloride  Room temperature  Reduction o Ester

 LiAlH4, dissolved in dry ether at room temperature

o Acyl chloride

 LiAlH4, dissolved in dry ether at room temperature

o Amide

 LiAlH4, dissolved in dry ether at room temperature

 b. Formation

 Acyl chloride

o Formation of acyl chloride by a halogen atom  Ester

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 Amide

o Acyl chloride, NH3/ RNH2/ R2’NH, cold

11. Amine

a. Reactions

 Alkylation of amine

o RX dissolved in ethanol in a sealed tube; Heat  Acylation of amine

o Acyl chloride; Cold b. Formation

 Reduction of nitriles

o LiAlH4, dry ether, room temperature

o H2(g) with Ni catalyst at 140oC

o Na and ethanol  Reduction of amides

o LiAlH4, dry ether, room temperature

o H2(g) with Ni catalyst at 140oC

o Na and ethanol

12. Phenylamine

a. Reactions

 Alkylation of amine

o RX dissolved in ethanol in a sealed tube; Heat  Acylation of amine

o Acyl chloride; Cold  Halogenation

o Br2 dissolved in CCl4

o Chlorine/ Bromine water at room temperature b. Formation

 Reduction of nitrobenzene

o Sn, concentrated HCl, reflux followed by addition of NaOH (aq)

13.

Halogenoalkane

a. Reactions

 Nucleophilic substitution o Alkaline hydrolysis

 NaOH (aq); Reflux  KOH (aq); Reflux o Formation of Nitrile

 Alcoholic KCN; Reflux o Formation of ether

 Na in excess alcohol; Reflux o Formation of ester

 Silver(I) salt of carboxylic acid in alcohol; Reflux o Formation of amine

 Excess concentrated NH3 in alcohol; Reflux

 Elimination

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 Alcoholic KOH; Reflux  Alcoholic CH3O-Na+; Reflux

b. Formation

 Free radical substitution of alkane  Halogenation of alcohols

Figure

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