ORGANIC REACTIONS NOTES Prepared by Baloyi DT hluvukahighschool@gmail.

com

There are five (5) main types of organic reactions

1. Combustion reaction (Complete : Burning in excess oxygen)

Alkane + O2 ⟶ CO2 + H2O + energy

2. Substitution reaction (2 types)

o Halogenation
o Hydrolysis

3. Addition (4 types) [Undergone by Alkenes only)

o Hydrogenation [Alkene + H2 → Alkane]

o Hydrogenation [Alkene + X2 → Haloalkane]
o Hydrohalogenation [Alkene + HX → Haloalkane], apply Markovnikov`s rule (Major product)
o Hydration [Alkene + H2O → Alcohol], apply Markovnikov`s rule (Major product)
4. Elimination reaction (3 types)

o (Thermal) Cracking [Long chain → Alkene + Alkane or H2]

o Dehydrohalogenation [Haloalkane (remove HX) → Alkene + HX], apply Zaitsev`s rule (Major
product)
o Dehydration [Alcohol (remove H2O) → Alkene + H2O], apply Zaitsev`s rule (Major product)

5. Condensation (Esterification)

Alcohol + Carboxylic acid ⟶ ester + water (conc. H2SO4 as a catalyst)

Organic reactions are undergone by the following Homologous series (4/5):

1. Alkanes
2. Alkenes
3. Haloalkanes
4. Alcohols / Carboxylic acids

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ORGANIC REACTIONS NOTES Prepared by Baloyi DT [email protected]

ORGANIC REACTIONS UNDERGONE BY HOMOLOGOUS SERIES

1. ALKANES (3 Organic Reactions)
1.1 Combustion (Complete)

Generally: Alkane + O2 ⟶ CO2 + H2O (Complete combustion: burning in excess oxygen)

E.g. Complete combustion of butane: 2C4H10 + 13O2 ⟶ 8CO2 + 10H2O
 This reaction is used as fuel during cooking or in vehicles.

1.2 Substitution (Halogenation)

Generally: Alkane + X2 ⟶ Haloalkane + Hydrogen halide (HX) where X = Cℓ or Br
H H H Br
H C C H + Br Br H C C H +H Br
H H H H
Ethane Bromine Chloroethane Hydrogen bromide
Molecular formula: C2H6 + Br2 ⟶ C2H5Br + HBr
Type of substitution: Halogenation (Bromination) Reactants: Alkane (Organic) and halogen (Inorganic)
Conditions: Heat or Sunlight Products: Haloalkane (Organic) and hydrogen halide (Inorganic)

1.3 Elimination (Thermal Cracking)

Generally: Alkane (long chain) ⟶ Alkane (short chain) + Alkene and/or Hydrogen
H H H H H
H H H H H
H C C C C C H H C C C H + C C

H H H H H H H H H H

Pentane Propane Ethane

Molecular formula: C5H12 ⟶ C3H8 + C2H4
Type of elimination: (Thermal) Cracking Reactants: Alkane (Organic)
Conditions: High temperatures and High pressures Products: Alkane + Alkene or H2

2. ALKENES (4 Organic Reactions)

2.1 Hydrogenation
Generally: Alkene + H2 ⟶ Alkane
H H
H H
C C + H2 H C C H
H H
H H
Ethene Hydrogen Ethane
Molecular structure: C2H4 + H2 ⟶ C2H6
Type of addition: Hydrogenation Reactants: Alkene (Organic) + Hydrogen {H2} (Inorganic)
Conditions: Pt, Ni or Pd as catalyst Products: Alkane (Organic)

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ORGANIC REACTIONS NOTES Prepared by Baloyi DT [email protected]

2.2 Halogenation

Generally: Alkene + X2 ⟶ Haloalkane [X2 = Br2 / Cl2]

H H
H H
C C + Cl Cl H C C H
H H Cl Cl
Ethene Chlorine 1,2 – dichloroethane
Molecular structure: C2H4 +Cl2 ⟶ C2H4Cl2
Type of addition: Halogenation (Chlorination) Reactants: Alkene (Organic) + Halogen {Cl2/Br2} (Inorganic)
Conditions: Unreactive solvent Products: Haloalkane (Organic)

2.3 Hydrohalogenation

Generally: Alkene + HX ⟶ Haloalkane [ X = Br / Cl]

H H H H H Br H

H C C C C + HBr H C C C C H
H
H H H H H H H
But – 1 – ene Hydrogen bromide 2 – bromobutane (Major product)
Molecular structure: C4H8 + HBr ⟶ C4H7Br
Type of addition: Hydrohalogenation (Hydrobromination) Reactants: Alkene (Organic) + Hydrogen bromide
Conditions: No water; Unreactive solvent Products: Haloalkane (Organic)
Major product: H atom attached to the C atom already having more H atoms (Markovnikov`s Rule)

2.4 Hydration

Generally: Alkene + H2O ⟶ Alcohol

H
H H H H H H
O
H C C C C + H2O H C C C C H
H
H H H H H H H
But – 1 – ene Water Butan – 2 – ol (Major product)
Molecular structure: C4H8 + H2O ⟶ C4H7OH / C4H8O
Type of addition: Hydration Reactants: Alkene (Organic) + H2O (Inorganic)
Conditions: Excess water; H2SO4 / H3PO4 as catalyst Products: Alcohol (Organic)
Major product: H atom attached to the C atom already having more H atoms (Markovnikov`s Rule)

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ORGANIC REACTIONS NOTES Prepared by Baloyi DT [email protected]

3. HALOALKANES (3 Organic Reactions)

3.1 Substitution (Hydrolysis)
3.1.1 with dilute strong base (NaOH/KOH)
Generally: Haloalkane + dil. Strong base (NaOH/KOH) ⟶ Alcohol + metal salt (NaBr/KBr/NaCl/KCl)

H
H H Br H H H H
O
H C C C C H + NaOH H C C C C H + Na Br

H H H H H H H H
2 - bromobutane sodium hydroxide butan – 2 – ol sodium bromide
Molecular structure: C4H7Br + NaOH ⟶ C4H7OH + NaBr
Type of substitution: Hydrolysis Reactants: Haloalkane + strong base (NaOH/KOH)
Conditions: Mild heat and Dilute strong base (NaOH/KOH) Products: Alcohol (Organic) + metal salt

3.1.2 with excess water (H2O)

Generally: Haloalkane + water ⟶ Alcohol + hydrogen halide (HBr/HCl)

H
H H Cl H H H H
O
H C C C C H + H2O H C C C C H + HCl

H H H H H H H H
2 - chlorobutane water butan – 2 – ol hydrogen chloride
Molecular structure: C4H7Cl + H2O ⟶ C4H7OH + HCl
Type of substitution: Hydrolysis Reactants: Haloalkane + water (H2O)
Conditions: Mild heat and excess water (H2O) Products: Alcohol (Organic) + hydrogen halide

3.2 Elimination (Dehydrohalogenation)

Generally: Haloalkane + conc. Strong base (NaOH/KOH) ⟶ Alkene + metal salt (NaBr/KBr/NaCl/KCl) + water (H2O)

H H Br H H H H
H C C C C H + NaOH H C C C C H + Na Br + H2O
H H H H H H H
2 - bromobutane sodium hydroxide but – 2 – ene (Major product) sodium bromide water
Molecular structure: C4H7Br + NaOH ⟶ C4H8 + NaBr + H2O
Type of elimination: Dehydrohalogenation Reactants: Haloalkane + conc. strong base(NaOH/KOH)
Conditions: Strong heat and Concentrated strong base (NaOH/KOH) Products: Alkene (Organic) + metal salt + water
Major product: The H atom is removed from the C atom with the least number of H atoms (Zaitsev`s Rule)

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ORGANIC REACTIONS NOTES Prepared by Baloyi DT [email protected]

4. ALCOHOLS
4.1 Substitution

Generally: Alcohol + HX (X = HBr/HCl) ⟶ Haloalkane + water (H2O)

H
H H H H H Br H
O
H C C C C H + HBr H C C C C H + H2O

H H H H H H H H
Butan – 2 - ol Hydrogen halide 2 – bromobutane Water
Molecular structure: C4H7OH + HBr ⟶ C4H7Br + H2O
Conditions: Heat
Reactants: Alcohol + Hydrogen halide (HBr/HCl) Products: Haloalkane (Organic) + water (Inorganic)

4.2 Elimination

Generally: Alcohol + ⟶ Alkene + water

H
H H H H H
O
H2SO4
H2O
H C C C C H H C C C C H +
H H H H H H H H
Butan – 2 – ol But – 2 – ene (Major product) water
Molecular structure: C4H7OH ⟶ C4H8 + H2O
Type of elimination: Dehydration Reactants: Alcohol + H2SO4 (Catalyst)
Conditions: H2SO4 as catalyst/dehydrating agent Products: Alkene (Organic) + water (H2O)
Major product: The H atom is removed from the C atom with the least number of H atoms (Zaitsev`s Rule)

4.3 Condensation / Esterification

Generally: Alcohol + Carboxylic acid ⟶ Ester + water

H H O H H H H O H H

H C C O H + H O C C C H H C C O C C C H
+ H2O
H H H H H H H H
Ethanol Propanoic acid Ethyl propanoate Water
Molecular structure: C2H5OH + C3H6O2 ⟶ C5H10O2 + H2O
Type of reaction: Condensation (Esterification)
Conditions: Heat and Concentrated Sulphuric acid (H2SO4) as catalyst
Reactants: Alcohol + Carboxylic acid (Organic) Products: Ester (Organic) + water (Inorganic)