SCH4U Organic Chemistry Revision

Organic Compounds
• Organic compounds are made of carbon with H,O,N.
• Carbon Dioxide and Carbon Monoxide are NOT organic compounds.

Why has Carbon been selected as the main element in organic compounds?

1) They have 4 valence shell electrons

2) They can form 4 covalent bonds

• Covalent bond: Non Metal + Non Metal, share electrons

• Properties:

• Contains Carbons

• Low Boiling & Melting Points

• Soluble

• Have Covalent bonds

• Burns in air (Combustion)

• Exothermic Reaction

Organic Structure:
Straight Chain Compounds Branched Chain Compouds Cyclic Compounds

IUPAC Naming + Rules:

#C Pre x 1) Select the Longest Chain

1 Meth
2) Find the functional group

3) Functional Group must be at the lowest carbon number

2 Eth 4) “-“ Between Alphabets + Numbers

5) “,” Between Numbers

3 Prop 6) Side Chain: Mono = 1, Di = 2, Tri = 3, Tetra = 4, Penta = 5

7) Side Chain: Follow Alphabetical Order

4 But
8) Halogens: Cl -> Chloro Br -> Bromo I -> Iodo

5 Pent 9) Numbering starts from side chain which has more number of group/substituents

6 Hex
Homologous Series:
Empirical Formula: Simplest Elemental Ratio

7 Hept - Same General Formula

Molecular Formula: How many atoms in each
- Similar Characteristics
element of compound

8 Oct - Same Functional Group

9 Non
- Same Chemical Reaction
MF: C₂H₆

Hydrocarbons:
EF: CH₃

10 Dec - Only contain Carbon and Hydrogen

Condensed Formula (CF): CH₃-CH₃
- C-C Tetrahedral Shape

11 Undec - C=C Trigonal Shape

12 Dodec - C三C Linear Shape

fi
Alkane:
Physical Properties:
• Non-Polar

• Insoluble in Water: Water is polar and Alkane is non-polar, so it cannot dissolve. Alkanes are soluble in non-
polar solvent. E.g. Benzene

• Boiling/Melting Point: As the molar mass increases, the intermolecular forces between the molecules
increases, so more energy is needed to break the bonds, hence the B.P/M.P increases.

• Tetrahedral Shape Bond Angle: 109.8°

• Saturated Compound (C-C)

• Viscosity: Viscosity increases as molar mass increases.

• Flammability: The ammability decreases as molar mass increases.

• Physical State: CH₄ —> C₄H₁₀ r.t.p Gas

C₅H₁₂ —> C₁₀H₂₂ r.t.p Liquid

C₁₁H₂₄—> r.t.p Solid

Chemical Properties:
• Combustion Reaction:

• Incomplete: Insu cient Oxygen, Less Energy, Orange Flame, Smoke Produced, Dangerous

• Products: CO₂ + CO + C + H₂O

• Complete: Su cient Oxygen, More Energy, Blue Flame, No Smoke

• Products: CO₂ + H₂O

• Substitution Reaction:
USES:

- Fuel (Gas/Lighters)

• CONDITIONS: U.V LIGHT

- Raw Material For Medicine

General Formula:

- CnH2n+2

Alkene/Alkyne:
Physical Properties (Alkene/Alkyne):
• Non-Polar

• Insoluble in Water: Water is polar and Alkene/Alkyne is non-polar, so it cannot dissolve. Alkene and Alkyne
are soluble in non-polar solvent. E.g. Benzene

• Boiling/Melting Point: As the molar mass increases, the intermolecular forces between the molecules
increases, so more energy is needed to break the bonds, hence the B.P/M.P increases.

• Trigonal Planar, Bond Angle: 120°

• Unsaturated

• Viscosity: Viscosity increases as molar mass increases.

• Flammability: The ammability decreases as molar mass increases.

• Physical State: C₂H₄ —> C₅H₁₀ r.t.p Gas

• Density: Density increases as molar mass increases.

Isomers: Compounds having the same molecular formula but di erent structural formula

CIS: Isomers that have two similar atoms on the same side of a carbon-carbon double bond

TRANS: Isomers that have two similar atoms placed on opposite sides of a carbon-carbon double
bond.

-CIS & TRANS form due to the restricted rotation about a C=C double bond.

Why is Olive Oil healthier than Margarine/Peanut Oil/Lard Oil?

1) Olive oil has more number of C=C compared to C-C, hence it is easier to digest in the
stomach. (Reference to Sigma & Pi bonds, sigma bond is more stronger than pi bond)
General Formula:

- Alkene/Cycloalkane: CnH2n Alkene: CnH2n-2

ffi
ffi
fl
fl
ff
Aromatic Compounds:

- Aroma (Smell)

- Must have Benzene Ring

- Benzene Ring:

• When the benzene ring is attached to a carbon chain, it loses one hydrogen-phenyl
group (C₆H₅)

IDP-IDP DP-DP Hydrogen Bonding

Induced Dipole Dipole -

In all Covalent Compounds Only in Polar Compounds O-H, H-F, N-H

Hydrogen Bonding > DP-DP > IDP-IDP

Intermolecular Force Intramolecular Force

CH₄````````CH₄ CH₄ (Strong)

Between the molecules In the Bonds

Functional Group
Formula Ending With Example
Name

Alcohol R-O-H OL CH₃OH (Methanol)

Aldehyde AL CH₃COH (Ethanal)

Ketone ONE CH₃COCH₃ (Propanone)

CH₃COOH (Ethanoic
Carboxylic Acid OIC ACID
Acid)

CH₃COOCH₃ (Methyl
Ester OATE
Ethanoate)

CH₃NH2 (Methanamine
Amine Amine
OR Methylamine)

CH₃OCH₃ (Methoxy
Ether R-O-R Alkoxy Alkane Methane)

Shortest Chain
Alcohol: General Formula:

- CnH2n+1OH
Physical Properties:
• Polar

• Solubility: Solubility decreases in water as we move from methanol —> pentanol. Smaller alcohols are soluble
in water. After ethanol, non-polar (alkyl group) increases, so the solubility decreases in water.



• Boiling/Melting Point: Increases from Methanol to pentanol because as Molar Mass increases, the H-bonding,
DP-DP and IDP-IDP forces increase between the molecules, hence more energy is needed to overcome the
bonds.

• Volatility: Decreases as Molar mass increases

• Physical State: CH₃OH —> C₅H₁₁OH r.t.p Liquid

Why does C₃H₇OH has a higher boiling point than C₃H₈?

1) Due to the hydrogen bonding and DP-DP force between the molecules in alcohol, it needs
more energy to overcome the bonds, hence the boiling point is higher.

• Primary Alcohol: Functional Group is attached to carbon which is attached to two H-atoms

• Secondary Alcohol: Functional Group is attached to carbon which is attached to one H-atoms

• Tertiary Alcohol: Functional Group is attached to carbon which is attached to 0 H-atoms

Chemical Properties:
• Combustion Reaction:

• Alcohol + Oxygen —> Carbon Dioxide + Water

• Oxidation Reaction:

• CONDITIONS: Acidi ed K₂CR₂O₇ Potassium Dichromate/ KMnO₄ Potassium Permanganate

• Observation: K₂CR₂O₇ (Orange to Green) KMnO₄ (Purple to Colourless)

• Primary Alcohol:

• After oxidation gives: Aldehyde then Carboxylic Acid

• Secondary Alcohol:

• After oxidation gives: Ketone

• Tertiary Alcohol:

• NO oxidation

• Preparation of Alcohol:

• Fermentation:

• Conditions: Yeast, 35°C ~ 37°C

• Glucose —> Alcohol + Carbon Dioxide (No oxygen)

• Hydration:

• Conditions: Concentrated Sulphuric Acid

• Alkene + Water —> Alcohol

Ether:
Physical Properties:
• Highly volatile & ammable

• Ethoxyethane is used as aesthetic

• Solubility: Soluble in water due to polarity of CO bond. As Molar mass increases, solubility increases because
the non-polar alkyl group increases.

• Bigger molecules of ether are soluble in fats and oils.

• Boiling Point: As molar mass increases, the boiling point increases.

Chemical Reaction:
• Condensation: When two molecules join together by removal of water

• C₂H₅OH + C₂H₅OH —> C₂H₅OC₂H₅ + H₂O

Naming:
R-O-R Alkoxy(Shorter Chain) - Alkane (Longer Chain)

Same molar mass of alkane & ether, which one will have a greater boiling point? Why?

1) Ether: High B.P, IDP-IDP, DP-DP

2) Alkane: Low B.P, IDP-IDP, No DP-DP

DP-DP>IDP-IDP Ether has dp-dp between molecules, dp-dp>idp-idp, hence more energy is needed to overcome the bonds
fl
fi
Thiol: General Formula:

Physical Properties: - CnH2n+1SH

• Functional Group-SH



• Ends with “thiols”

• Very strong odour due to the presence of sulphur

• Neutralised by H₂O₂ (Bleach)

Aldehyde: General Formula:

- CnH2n+1CHO
Physical Properties:
• Carbonyl Compound due to C=O

• B.P increases, M.P increases, as MR increases, IDP IDP increases, dp dp increases between molecules

• Polar

• Soluble in water (small molecules) As Mr increases, solubility decreases

• Very Smelly

• Making of Aldehyde: Primary Alcohol undergoes oxidation

• Reaction of Aldehyde:

• Combustion: CH₃CHO + O₂ —>CO₂ + CO

• Reduction:

• CONDITIONS: Ni, 300°C

Ketone: OH<CHO<CO<COOH
• When ketone is in a side chain, then it is called as “oxo”.

Physical Properties:
• Boiling Point increases as Molar mass increases

• Solubility decreases as Molar Mass increases

• Polar due to the presence of C=O

Chemical Properties:
• Making of Ketone: Secondary alcohol undergoing oxidation

• Combustion: R-C=O-R + O₂ —> CO₂ + H₂O + energy

• Reduction: Conditions: Ni + 300°C

Carboxylic Acid: General Formula:

• COOH>CO>CHO>OH
- CnH2n+1COOH
Physical Properties:
• Solubility: Soluble in water. Solubility decreases as Molar mass increases.

• Non-Polar

• B.P increases as Molar Mass increases

• Viscosity increases as Molar Mass increases

• Physical State: Most are liquid at r.t.p

• Zero Flammability

Weak Acid-Partially dissociates into ions when dissolved in water (Reversible)

• CH₃COOH <—> CH₃COO⁻ + H⁺

Chemical Properties:
• Able to conduct electricity when dissolved in water due to the presence of free ions.

• ACID + METAL -> SALT + H₂(g)

• ACID + METAL CARBONATE -> SALT + CO₂ + H₂O

• Neutralisation:

• ACID + ALKALI —> SALT + H₂O

• CH₃COOH + NaOH —> CH₃COONa + H₂O

Esters:
Physical Properties:
• Insoluble in water

• Polar

• B.P/M.P/Density increases as Molar Mass increases

• Lower Molar mass esters are volatile

• Sweet Smelling liquid (e.g. vanilla)

• Low Molar mass esters are gases, most are liquids.

Esteri cation: The process of condensation(when two molecules join together by removing water)

CONDITIONS: Concentrated Sulphuric acid + Heat

Reagent: Alcohol + Carboxylic Acid

Chemical Reaction:
• Hydrolysis: Add water to break down

• CONDITIONS: aqueous NaOH or aq KOH, heat

• R-(C=O)-O-R + NaOH —> R-(C=O)-O-Na (salt) + R-OH (alcohol)

Uses:
- Ice cream avours

- Perfume

- Solvent

- Drugs contain esters, they are insoluble in water but soluble in fats. Hence it goes into the brain, making one
high.

fi
fl