H2 Organic Chemistry Reaction Summary | Ingel Soong

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H2 Organic Chemistry Reaction Summary for Elucidation and Deductive Questions

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Comparison of Alcohol, Water, Phenol and Carboxylic Acid Reactivities

alcohol water phenol acid reactivity

Comparison of LiAl4, NaBH4, H2 Reduction Reactions

LiAlH4 NaBH4 H2

Links

  • Reactions of

Alkane, Alkene, Halogenoalkane, Nitrile, Alcohol, Carbonyl Compounds,
Carboxylic Acid, Acyl Chloride, Ester, Nitrogen Compounds

  • Formation of

Alkane, Alkene, Halogenoalkane
Nitrile, Alcohol, Carbonyl Compounds
Carboxylic Acid, Acyl Chloride, Ester, Amine, Amide

  • Reactions of

Benzene, Methylenzene, Phenol, Aryl Chloride, Aryl Nitro

Aliphatic Compounds

The following is a summary of reaction for hydrocarbons (alkane, alkene, alkyl hydrogensulfate), hydrogen derivatives (halogenoalkane), hydroxyl compounds (alcohol), carbonyl compounds (aldehydes, ketones), carboxylic acids and derivatives (carboxylic acid, acyl chloride, ester), nitrogen compounds (nitrile, amine, amide, amino acid).

Reactions of Alkane

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halogenoalkane

Halogenoalkane

Reagents:
Cl2 gas (or Br2 gas)

Reaction:
Free radical substitution

Observations:
Greenish yellow Cl2 decolorised
(or reddish brown Br2 decolorised)
White fumes of HCl formed

Reactions of Alkene

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alkane

Alkane

Reagents:
H2/Ni, heat

Reaction:
Reduction

Observations:

halogenoalkane

Halogenoalkane

Reagents:
Cl2 in CCl4 (or Br2 in CCl4)

Reaction:
Electrophilic addition

Observations:
Greenish yellow Cl2 decolorised
(or reddish brown Br2 decolorised)

halogenoalkane

Halogenoalkane

Reagents:
HCl gas, rtp

Reaction:
Electrophilic addition

Observations:

alcohol

Alcohol

Reagents:
H2O, 300oC, 60atm, conc. H3PO4

Reaction:
Electrophilic addition

Observations:

diol

Diol

Reagents:
Cold dilute KMnO4

Reaction:
Mild Oxidation

Observations:
Purple KMnO4 decolorized.
Brown MnO2 ppt formed in alkaline conditions

carboxylic acid

Carboxylic Acid

Reagents:
Hot acidified KMnO4

Reaction:
Oxidative cleavage

Observations:
Purple KMnO4 decolorized.
Brown MnO2 ppt formed in alkaline conditions

carbon dioxide

Carbon dioxide

Reagents:
Hot acidified KMnO4

Reaction:
Oxidative cleavage for terminal alkenes only

Observations:
Purple KMnO4 decolorized.

Reactions of Halogenoalkane

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alkene

Alkene

Reagents:
NaOH (alc), heat under reflux

Reaction:
Elimination

Observations:

alcohol

Alcohol

Reagents:
NaOH(aq), heat under reflux

Reaction:
Nucleophilic substitution

Observations:

amine

Amine

Reagents:
Excess NH3 (alc), heated in a sealed tube

Reaction:
Nucleophilic substitution

Observations:

nitrile

Nitrile

Reagents:
NaCN (alc), heat under reflux

Reaction:
Nucleophilic substitution

Observations:

Reactions of Nitrile

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carboxylic acid

Carboxylic acid

Reagents:
Dilute H2SO4, heat

Reaction:
Acid hydrolysis

Observations:

carboxylate ion

Carboxylate ion

Reagents:
Dilute NaOH, heat

Reaction:
Basic hydrolysis

Observations:

alkyl ammonium

Amine

Reagents:
LiAlH4, dry ether
(or H2, Pd)

Reaction:
Reduction

Observations:

Reactions of Alcohol

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halogenoalkane

Halogenoalkane

Reagents:
PCl3 (or PCl5 or SOCl2)
Conc HCl, anhydrous ZnCl2, heat (for 1o and 2o alcohols only)
PBr3 from Br2 and red P
HBr gas from NaBr and H2SO4, heat
PI3 from I2 and red P

Reaction:
Substitution

Observations:
HCl fumes for PCl3/PCl5/SOCl2 only

alkoxide

Alkoxide ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H2 gas formed which gives pop sound with lighted splint

carboxylic acid

Carboxylic acid

Reagents:
1o alcohol only.
KMnO4, heat (or K2CrO4, heat)

Reaction:
Oxidation

Observations:
Purple KMnO4 decolorised
(or orange K2CrO4 turned green)

aldehyde

Aldehyde

Reagents:
1o alcohol only.
K2CrO4, heat with distillation

Reaction:
Oxidation

Observations:
Orange K2CrO4 turned green

ketone

Ketone

Reagents:
2o alcohol only.
KMnO4, heat (or K2CrO4, heat)

Reaction:
Oxidation

Observations:
Purple KMnO4 decolorised
(or orange K2CrO4 turned green)

alkene

Alkene

Reagents:
Excess conc. H2SO4, 1700C
(or Al2O3)

Reaction:
Elimination

Observations:

carboxylate ion

Carboxylate ion

Reagents:
I2, NaOH, heat

Reaction:
Mild oxidation

Observations:
Yellow CHI3 ppt formed

ester

Ester

Reagents:
Acid, conc H2SO4, heat
(or acyl chloride, rtp)

Reaction:
Condensation

Observations:
Sweet smell of ester

Reactions of Carbonyl Compound

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carboxylic acid

Acid

Reagents:
KMnO4, heat (or K2CrO4, heat)

Reaction:
Oxidation

Observations:
Purple KMnO4 decolorised
(or orange K2CrO4 turned green)

alcohol

Alcohol

Reagents:
NaBH4 (aq), (or LiAlH4 in dry ether, H2 gas, Pt heat)

Reaction:
Reduction
(Aldehyde to 1o alcohol
Ketone to 2o alcohol)

Observations:

hydrazone

2,4-DNPH

Reagents:
2,4-DNPH, warm

Reaction:
Condensation

Observations:
Orange ppt of hydrazone formed

carboxylate ion

Carboxylate ion

Reagents:
I2, NaOH, heat

Reaction:
Oxidation

Observations:
Yellow CHI3 ppt formed

carboxylate ion

Carboxylate ion

Reagents:
Fehling’s solution (Cu2+ and NaOH), warm
Aldehyde (except benzaldehyde) only

Reaction:
Oxidation

Observations:
Brick red of Cu2O ppt formed

carboxylate ion

Carboxylate ion

Reagents:
Tollen’s reageant (Ag2O in NH3)
Aldehyde only

Reaction:
Oxidation

Observations:
Silver mirror of Ag formed

Reactions of Carboxylic Acid

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carboxylate ion

Carboxylate ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H2 gas formed which gives pop sound with lighted splint

carboxylate ion

Carboxylate ion

Reagents:
NaOH(aq)

Reaction:
Neutralisation

Observations:

carboxylate ion

Carboxylate ion

Reagents:
Na2CO3 (or NaHCO3)

Reaction:
Neutralisation

Observations:
Effervescence of CO2 gas formed which gives white ppt with limewater

ethanoyl chloride

Acyl chloride

Reagents:
PCl3 (or PCl5 or SOCl2)

Reaction:
Neutralisation

Observations:
White fumes of HCl

ester

Ester

Reagents:
Alcohol, conc H2SO4, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

alcohol

Alcohol

Reagents:
LiAlH4 in dry ether

Reaction:
Reduction to 1o alcohol

Observations:

carbon dioxide

Carbon dioxide

Reagents:
KMnO4, heat
HCOOH or (COOH)2

Reaction:
Purple KMnO4 decolorized.
Effervescence of CO2 gas formed which gives white ppt with limewater

Observations:

Reactions of Acyl Chloride

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ester

Ester

Reagents:
Alcohol, conc H2SO4, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

amide

Amide

Reagents:
Excess conc NH3

Excess RNH2
1o amine to 2o amide
2o amine to 3o amide
no reaction for 3o amide

Reaction:
Condensation

Observations:
White fumes of HCl

alcohol

Alcohol

Reagents:
H2O

Reaction:
Hydrolysis

Observations:
White fumes of HCl

Reactions of Ester

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carboxylic acid

Carboxylic acid

Reagents:
Dilute H2SO4, heat under reflux

Reaction:
Acid hydrolysis

Observations:

carboxylate ion

Carboxylate ion

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Basic hydrolysis

Observations:

Reactions of Nitrogen Compound

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alkyl ammonium

Alkyl ammonium and carboxylic acid

Reagents:
HCl(aq)
(or CH3COOH)

Reaction:
Neutralisation

Observations:
White crystalline solid

N-alkylamine

N-alkylamine

Reagents:
CH3Cl, heat

Reaction:
Nucleophilic substitution

Observations:

amide

Amide

Reagents:
Acyl chloride

Reaction:
Condensation

Observations:
White fumes of HCl

alkyl ammonium
carboxylic acid

Alkyl ammonium

Reagents:
Dilute H2SO4, heat under reflux

Reaction:
Acid hydrolysis
1o amide produce NH4+

Observations:

carboxylate ion
amine

Carboxylate ion and amine

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Base hydrolysis
1o amide produce NH3

Observations:
NH3 gas turned damp red litmus paper blue

Formation of Alkane

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alkene

Alkene

Reagents:
H2/Ni, heat

Reaction:
Reduction

Observations:

Formation of Alkene

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alcohol

Alcohol

Reagents:
Excess conc. H2SO4, 1700C
(or Al2O3)

Reaction:
Elimination

Observations:

Formation of Halogenoalkane

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alkene

Alkene

Reagents:
Cl2 in CCl4 (or Br2 in CCl4)

Reaction:
Electrophilic addition

Observations:
Greenish yellow Cl2 decolorised
(or reddish brown Br2 decolorised)

alkene

Alkene

Reagents:
HCl gas, rtp

Reaction:
Electrophilic addition

Observations:

alkene

Alkene

Reagents:
PCl3 (or PCl5 or SOCl2)
Conc HCl, anhydrous ZnCl2, heat (for 1o and 2o alcohols only)
PBr3 from Br2 and red P
HBr gas from NaBr and H2SO4, heat
PI3 from I2 and red P

Reaction:
Substitution

Observations:
HCl fumes for PCl3/PCl5/SOCl2 only

Formation of Alcohol

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halogenoalkane

Halogenoalkane

Reagents:
NaOH (aq), heat under reflux

Reaction:
Nucleophilic substitution

Observations:

alkene

Alkene

Reagents:
H2O, 300oC, 60atm, conc. H3PO4

Reaction:
Electrophilic addition

Observations:

aldehyde

Carbonyl Compound

Reagents:
NaBH4 (aq), (or LiAlH4 in dry ether, H2 gas, Pt heat)

Reaction:
Reduction
(Aldehyde to 1o alcohol
Ketone to 2o alcohol)

Observations:

carboxylic acid

Carboxylic Acid

Reagents:
LiAlH4 in dry ether

Reaction:
Reduction to 1o alcohol

Observations:

Formation of Carboxylic Acid

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alkene

Alkene

Reagents:
Hot acidified KMnO4

Reaction:
Oxidative cleavage

Observations:
Purple KMnO4 decolorized.
Brown MnO2 ppt formed in alkaline conditions

ester

Ester

Reagents:
Dilute H2SO4, heat

Reaction:
Acid hydrolysis

Observations:

alcohol

Alcohol

Reagents:
1o alcohol only.
KMnO4, heat (or K2CrO4, heat)

Reaction:
Oxidation

Observations:
Purple KMnO4 decolorised
(or orange K2CrO4 turned green)

alcohol

Alcohol

Reagents:
I2, NaOH, heat

Reaction:
Mild oxidation

Observations:
Yellow CHI3 ppt formed

amide

Amide

Reagents:
HCl(aq)
(or CH3COOH)

Reaction:
Neutralisation

Observations:
White crystalline solid

Formation of Acyl Chloride

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carboxylic acid

Carboxylic acid

Reagents:
PCl3 (or PCl5 or SOCl2)

Reaction:
Neutralisation

Observations:
White fumes of HCl

Formation of Ester

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alcohol

Alcohol

Reagents:
Acid, conc H2SO4, heat
(or acyl chloride, rtp)

Reaction:
Condensation

Observations:
Sweet smell of ester

carboxylic acid

Carboxylic acid

Reagents:
Alcohol, conc H2SO4, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

ethanoyl chloride

Acyl Chloride

Reagents:
ALcohol, conc H2SO4, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

Formation of Amine

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halogenoalkane

Halogenoalkane

Reagents:
Excess NH3 (alc), heated in a sealed tube

Reaction:
Nucleophilic substitution

Observations:

nitrile

Nitrile

Reagents:
LiAlH4, dry ether
(or H2, Pd)

Reaction:
Reduction

Observations:

amide

Amide

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Base hydrolysis
1o amide produce NH3

Observations:
NH3 gas turned damp red litmus paper blue

Formation of Amide

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ethanoyl chloride

Acyl chloride

Reagents:
Excess conc NH3

Excess RNH2
1o amine to 2o amide
2o amine to 3o amide
no reaction for 3o amide

Reaction:
Condensation

Observations:
White fumes of HCl

Aromatic Compounds

The following is a summary of reaction for hydrocarbons (benzene), hydroxyl compounds (phenol), carboxylic acids and derivatives (benzoic acid, benzoate), nitrogen compounds (phenylamine, nitrobenzene):

Reactions of Benzene

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nitrobenzene

Nitrobenzene

Reagents:
Conc HNO3, conc H2SO4, heat under reflux at 55oC

Reaction:
Electrophilic substitution

Observations:
Yellow layer of nitrobenzene formed

bromobenzene

Nitrobenzene

Reagents:
Br2, anhydrous FeBr3, rtp
(or Cl2, anhydrous FeCl3, rtp)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br2 decolorised
(or greenish yellow Cl2 decolorised)

Reactions of Methylbenzene

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1-methyl-2-nitrobenzene

1-methyl-4-nitrobenzene

1-methyl,2-nitrobenzene

Reagents:
Conc HNO3, conc H2SO4, heat under reflux at 30oC

Reaction:
Electrophilic substitution

Observations:

1-bromo-2-nitrobenzene1-bromo-4-nitrobenzene

1-bromo-2-nitrobenzene

Reagents:
Br2, anhydrous FeBr3, rtp
(or Cl2, anhydrous FeCl3, rtp)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br2 decolorised
(or greenish yellow Cl2 decolorised)

chloromethylbenzene

1-bromo-2-nitrobenzene

Reagents:
Cl2, UV light, boil

Reaction:
Free radical substitution

Observations:
Greenish yellow Cl2 decolorised
White fumes of HCl formed

benzoic acid

Benzoic acid

Reagents:
Hot acidified KMnO4, heat under reflux

Reaction:
Side chain oxidation

Observations:
Purple KMnO4 decolorised
White benzoic acid ppt formed

Reactions of Phenol

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phenoxide anion

Phenoxide ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H2 gas formed which gives pop sound with lighted splint

methyl benzoate

Phenyl benzoate

Reagents:
CH3Cl, pyridine, rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

phenyl benzoate

Phenyl benzoate

Reagents:
Phenylacetyl chloride, NaOH(aq), rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

1,3,5-tribromobenzene

1,3,5-tribromobenzene

Reagents:
Br2(aq), rtp

Reaction:
Condensation

Observations:
Reddish brown Br2 decolorized
White 1,3,5-tribromobenzene ppt formed
White fumes of HBr formed

1-bromo-4-nitrobenzene1-bromo-2-nitrobenzene

Nitrophenol

Reagents:
Dilute HNO3(aq), rtp

Reaction:
Electrophilic substitution

Observations:
Yellow layer of nitrophenol formed

1,3,5-trinitrobenzene

1,3,5-trinitrophenol

Reagents:
Conc HNO3(aq), rtp

Reaction:
Electrophilic substitution

Observations:
Yellow ppt of 1,3,5-trinitrophenol formed

1,3,5-trinitrophenol

Reagents:
Neutral FeCl3(aq)

Reaction:
Electrophilic substitution

Observations:
Violet complex compound formed

Reactions of Aryl Chloride

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phenyl benzoate

Phenyl benzoate

Reagents:
Phenol, NaOH(aq), rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

Reactions of Aryl Nitro Compounds

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phenylamine

Phenylamine

Reagents:
Sn, conc HCl, heat followed by NaOH (or H2, Ni, heat)

Reaction:
Reduction

Observations:
Sweet smell of ester
White fumes of HCl formed

phenylamine
2,4,6-tribromophenylamine

2,4,6-tribromophenylamine

Reagents:
Br2(aq)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br2 decolorized
White 2,4,6-tribromophenylamine ppt formed
White fumes of HBr formed

Summary Map of Alipahtic Reactions

Summary Map of Aromatic Reactions

H2 Organic Chemistry Aromatic Reaction Summary

Comment

2 Replies to “H2 Organic Chemistry Reaction Summary | Ingel Soong”

  1. This is certainly pleasing to the eyes. Thank you for making the dreaded organic chemistry much more appealing

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