Cambridge IGCSE0620

Formulae, functional groups and terminology

Chemistry 0620 Chapter Notes

What this chapter covers

Formulae, functional groups and terminologyNaming organic compoundsFuelsAlkanesAlkenesAlcoholsCarboxylic acidsPolymers
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1. Understanding Homologous Series

In organic chemistry, compounds are grouped into 'families' called homologous series. Think of it like a family of people who share a surname and have similar features. All compounds in a homologous series share the same functional group (the reactive part of the molecule), which means they have similar chemical properties. They also share a general formula. As you go from one member to the next in a series, the carbon chain gets longer by one carbon and two hydrogen atoms (a -CH2- group). This causes a gradual change in physical properties, such as an increase in boiling point, as the molecules get larger.

Alkanes: CₙH₂ₙ₊₂

Alkenes: CₙH₂ₙ

Alcohols: CₙH₂ₙ₊₁OH

Carboxylic Acids: CₙH₂ₙ₊₁COOH (for n=0, 1, 2...)

Key term

Homologous Series: A family of organic compounds with the same functional group and similar chemical properties, where successive members differ by a CH₂ group.

Examiner insight

Examiners expect you to list at least two distinct characteristics of a homologous series, such as having the same general formula and showing a gradual change in physical properties.

Worked example 13 marks

State three features of a homologous series.

  1. 1
    1. Recall the definition of a homologous series. The key features are what define the series.
  2. 2
    1. Feature 1: All members have the same general formula (e.g., CₙH₂ₙ₊₂ for alkanes).
  3. 3
    1. Feature 2: All members have the same functional group, which gives them similar chemical properties (e.g., the C=C bond in alkenes).
  4. 4
    1. Feature 3: Successive members differ by a -CH₂- group.
  5. 5
    1. Feature 4 (optional but good): There is a gradual trend in physical properties, such as boiling points, as the chain length increases.

Recap

  • A homologous series is a family of organic compounds.
  • Members share the same functional group and have similar chemical reactions.
  • They all fit the same general formula.
  • Each member differs from the next by a -CH₂- unit.
  • Physical properties like boiling point change gradually down the series.

Quick check

  1. What is the general formula for the alkenes?1 mark
  2. By which atomic group do successive members of a homologous series differ?1 mark

2. Naming Organic Compounds

Organic compound names are very logical. They usually have two parts. The first part (prefix) tells you the number of carbon atoms in the main chain. The second part (suffix) tells you which homologous series the compound belongs to (i.e., its functional group). For example, 'eth-' means 2 carbons, and '-ane' means it's an alkane. So, 'ethane' is an alkane with 2 carbon atoms.

Key term

Nomenclature: The internationally agreed system of rules for naming chemical compounds.

Common pitfall

Mixing up the prefixes, especially 'prop-' (3 carbons) and 'but-' (4 carbons), or 'meth-' (1) and 'eth-' (2).

Worked example 12 marks

A compound has the structural formula CH₃-CH₂-CH₂-OH. What is its name?

  1. 1
    1. Identify the number of carbon atoms in the longest chain. There are three carbon atoms.
  2. 2
    1. The prefix for three carbons is 'prop-'.
  3. 3
    1. Identify the functional group. The -OH group indicates it is an alcohol.
  4. 4
    1. The suffix for an alcohol is '-ol'.
  5. 5
    1. Combine the parts: 'prop' + 'an' + 'ol' gives 'propanol'. (Specifically, propan-1-ol as the OH is on the end carbon).

Worked example 22 marks

What is the molecular formula of pentanoic acid?

  1. 1
    1. Identify the prefix. 'Pent-' means 5 carbon atoms in total.
  2. 2
    1. Identify the suffix. '-oic acid' means it is a carboxylic acid, with the functional group -COOH.
  3. 3
    1. The -COOH group contains one of the 5 carbon atoms. This leaves 4 other carbon atoms in the chain (C₄H₉).
  4. 4
    1. The full formula is therefore C₄H₉COOH. To write a molecular formula, sum all atoms: 5 carbons, 10 hydrogens (9+1), and 2 oxygens.
  5. 5
    1. The molecular formula is C₅H₁₀O₂.

Recap

  • The start of the name (prefix) indicates the number of carbon atoms: meth- (1), eth- (2), prop- (3), but- (4).
  • The end of the name (suffix) indicates the family: -ane (alkane), -ene (alkene), -ol (alcohol), -oic acid (carboxylic acid).
  • To name a compound, count the carbons to find the prefix and identify the functional group to find the suffix.

Quick check

  1. What is the prefix for an organic compound with 4 carbon atoms?1 mark
  2. A compound's name ends in '-ene'. To which homologous series does it belong?1 mark

3. Alkanes: Saturated Hydrocarbons

Alkanes are the simplest homologous series. They are hydrocarbons, meaning they contain only carbon and hydrogen atoms. They are described as 'saturated' because all the carbon-to-carbon bonds are single bonds. This makes them relatively unreactive. Their main reaction is combustion (burning), which releases a lot of energy, making them excellent fuels. Natural gas is mostly methane, the simplest alkane.

General Formula: CₙH₂ₙ₊₂

Complete Combustion: Alkane + Oxygen → Carbon Dioxide + Water

Example (Propane): C₃H₈(g) + 5O₂(g) → 3CO₂(g) + 4H₂O(l)

Key term

Saturated: An organic compound containing only single carbon-carbon bonds, with no capacity to add more atoms.

Examiner insight

When drawing displayed formulae for alkanes, ensure every carbon atom is shown with exactly four single bonds and every hydrogen with one.

Fun fact

The 'wax' on the surface of an apple's skin is made of a mixture of long-chain alkanes, which helps to keep moisture in.

Worked example 13 marks

Draw the displayed formula for ethane, C₂H₆, and write a balanced equation for its complete combustion.

  1. 1
    1. For the displayed formula, 'eth-' means 2 carbons. Draw two C atoms joined by a single bond: C-C.
  2. 2
    1. Alkanes are saturated, so each carbon must have 4 single bonds in total. Add H atoms to each carbon until it has 4 bonds. This results in 3 H atoms on each C.
  3. 3
    1. The final structure is H₃C-CH₃, with all bonds shown.
  4. 4
    1. For combustion, the reactants are ethane (C₂H₆) and oxygen (O₂). The products of complete combustion are carbon dioxide (CO₂) and water (H₂O).
  5. 5
    1. Write the unbalanced equation: C₂H₆ + O₂ → CO₂ + H₂O.
  6. 6
    1. Balance the carbons: 2 C on the left, so 2CO₂ on the right. C₂H₆ + O₂ → 2CO₂ + H₂O.
  7. 7
    1. Balance the hydrogens: 6 H on the left, so 3H₂O on the right. C₂H₆ + O₂ → 2CO₂ + 3H₂O.
  8. 8
    1. Balance the oxygens: On the right, there are (2×2) + (3×1) = 7 oxygen atoms. So we need 3.5 O₂ molecules. C₂H₆ + 3.5O₂ → 2CO₂ + 3H₂O.
  9. 9
    1. Double the whole equation to avoid fractions: 2C₂H₆ + 7O₂ → 4CO₂ + 6H₂O.

Recap

  • Alkanes are saturated hydrocarbons.
  • Saturated means all carbon-carbon bonds are single.
  • Their general formula is CₙH₂ₙ₊₂.
  • Alkanes are relatively unreactive but undergo complete combustion to form CO₂ and H₂O.

Quick check

  1. What is the molecular formula of the alkane with 5 carbon atoms?1 mark

4. Alkenes and Unsaturation

Alkenes are hydrocarbons that are 'unsaturated'. This means they contain at least one carbon-carbon double bond (C=C). This double bond is the alkene's functional group. It is a site of high electron density, making alkenes much more reactive than alkanes. They undergo addition reactions, where the double bond breaks and atoms are added to the carbon atoms. A key test for unsaturation is adding the alkene to bromine water (an orange solution). The alkene will decolourise the bromine water as an addition reaction occurs.

General Formula: CₙH₂ₙ

Addition Reaction with Bromine: C₂H₄ + Br₂ → C₂H₄Br₂

Key term

Functional Group: An atom or group of atoms in a molecule that is responsible for its characteristic chemical reactions.

Common pitfall

Forgetting that the double bond breaks and becomes a single bond during an addition reaction. The product is always saturated.

Worked example 13 marks

Propene (C₃H₆) is an alkene.(a) Draw its displayed formula.(b) Describe what you would observe when propene gas is bubbled through aqueous bromine.

  1. 1

    (a) 'Prop-' means 3 carbons. '-ene' means a C=C double bond. Draw three carbons in a chain with one double bond: C=C-C.

  2. 2

    (a) Now, add hydrogen atoms so that each carbon has exactly 4 bonds in total. The first C gets 2 H's, the second C gets 1 H, and the third C gets 3 H's. The structure is CH₂=CH-CH₃.

  3. 3

    (b) Alkenes are unsaturated due to the C=C bond.

  4. 4

    (b) They undergo an addition reaction with bromine.

  5. 5

    (b) Aqueous bromine is an orange-brown solution.

  6. 6

    (b) The observation is that the orange-brown colour of the bromine water disappears; it becomes colourless.

Recap

  • Alkenes are unsaturated hydrocarbons with the general formula CₙH₂ₙ.
  • Their functional group is the carbon-carbon double bond (C=C).
  • The C=C bond makes them reactive, and they undergo addition reactions.
  • Alkenes decolourise orange bromine water in an addition reaction, which is the test for unsaturation.

Quick check

  1. What is the functional group in all alkenes?1 mark
  2. What is the positive result for the test for an unsaturated hydrocarbon using aqueous bromine?1 mark

5. The Alcohol Family

Alcohols are a homologous series that are not hydrocarbons because they contain oxygen. They are similar to alkanes, but one hydrogen atom has been replaced by a hydroxyl (-OH) functional group. The general formula is CₙH₂ₙ₊₁OH. Ethanol is the most well-known alcohol, used as a solvent, in alcoholic drinks, and as a fuel. Alcohols can be made by fermentation of sugars or by hydrating alkenes. They burn cleanly and can be oxidised to form carboxylic acids.

General Formula: CₙH₂ₙ₊₁OH

Functional Group: -OH

Combustion of Ethanol: C₂H₅OH + 3O₂ → 2CO₂ + 3H₂O

Key term

Hydroxyl Group: The -OH functional group, consisting of an oxygen atom covalently bonded to a hydrogen atom, which is characteristic of alcohols.

Examiner insight

Be careful not to confuse the covalently bonded -OH group in alcohols with the hydroxide ion (OH⁻) found in inorganic alkalis like NaOH.

Fun fact

The 'proof' system for alcohol content originated from a test where a pellet of gunpowder was soaked in the spirit. If the gunpowder could still ignite, the spirit was 'proved' to be of a high enough standard.

Worked example 13 marks

Methanol (CH₃OH) is the simplest alcohol.(a) Draw its displayed formula.(b) It can be used as a fuel. Write a balanced equation for its complete combustion.

  1. 1

    (a) The formula is CH₃OH. Draw the carbon atom bonded to three hydrogen atoms and the oxygen atom. The oxygen atom is then bonded to the final hydrogen atom. Ensure C has 4 bonds and O has 2.

  2. 2

    (b) Complete combustion produces carbon dioxide (CO₂) and water (H₂O).

  3. 3

    (b) Write the unbalanced equation: CH₃OH + O₂ → CO₂ + H₂O.

  4. 4

    (b) Balance C: 1 on left, 1 on right. Balanced.

  5. 5

    (b) Balance H: 4 on left (3+1), so need 2H₂O on right. CH₃OH + O₂ → CO₂ + 2H₂O.

  6. 6

    (b) Balance O: 4 on right (2 + 2). On left, 1 in CH₃OH, so need 3 more from O₂. This means 1.5 O₂ molecules. CH₃OH + 1.5O₂ → CO₂ + 2H₂O.

  7. 7

    (b) Double the entire equation to remove the fraction: 2CH₃OH + 3O₂ → 2CO₂ + 4H₂O.

Recap

  • Alcohols contain the hydroxyl (-OH) functional group.
  • Their names end in '-ol', e.g., ethanol.
  • Their general formula is CₙH₂ₙ₊₁OH.
  • Alcohols are used as solvents and fuels.
  • They undergo complete combustion to produce carbon dioxide and water.

Quick check

  1. Name the alcohol containing 3 carbon atoms where the -OH group is on the end carbon.1 mark

6. Carboxylic Acids

Carboxylic acids are a homologous series containing the carboxyl (-COOH) functional group. Their names end in '-oic acid', for example, ethanoic acid (found in vinegar). They are weak acids, which means that when dissolved in water, only a small proportion of their molecules dissociate (split up) to release H⁺ ions. Despite being weak, they still show typical acid reactions: they react with metals, bases (alkalis), and carbonates to form salts.

Functional Group: -COOH

Dissociation of a Weak Acid: CH₃COOH(aq) ⇌ CH₃COO⁻(aq) + H⁺(aq)

Reaction with a Carbonate: 2CH₃COOH + Na₂CO₃ → 2CH₃COONa + H₂O + CO₂

Key term

Weak Acid: An acid that only partially ionises or dissociates in aqueous solution to produce H⁺ ions.

Common pitfall

Drawing the -COOH group incorrectly. The carbon is double-bonded to one oxygen and single-bonded to an -OH group. It is not C-O-O-H.

Fun fact

The sting of a red ant contains methanoic acid, the simplest carboxylic acid.

Worked example 13 marks

Propanoic acid (C₂H₅COOH) is a typical carboxylic acid. Write a balanced chemical equation for its reaction with magnesium oxide (MgO).

  1. 1
    1. Identify the reactants: a carboxylic acid (propanoic acid) and a metal oxide (magnesium oxide). This is an acid + base reaction.
  2. 2
    1. Recall that acid + base → salt + water.
  3. 3
    1. The salt is formed from the metal cation (Mg²⁺) and the carboxylate anion (C₂H₅COO⁻). To balance the charges, two propanoate ions are needed for every one magnesium ion. The salt's formula is (C₂H₅COO)₂Mg.
  4. 4
    1. The other product is water (H₂O).
  5. 5
    1. Write the unbalanced equation: C₂H₅COOH + MgO → (C₂H₅COO)₂Mg + H₂O.
  6. 6
    1. Balance the propanoate group: There are 2 on the right, so we need 2 C₂H₅COOH on the left. 2C₂H₅COOH + MgO → (C₂H₅COO)₂Mg + H₂O.
  7. 7
    1. Check the other atoms. Mg is balanced (1 and 1). H and O in the acid/base reaction are balanced (2H from the acid's -COOH and 1 O from MgO form one H₂O). The equation is now balanced.

Recap

  • Carboxylic acids contain the carboxyl (-COOH) functional group.
  • Their names end in '-oic acid'.
  • They are weak acids, only partially dissociating in water.
  • They react with metals, bases, and carbonates to form salts.
  • Reaction with carbonates produces carbon dioxide gas, causing fizzing.

Quick check

  1. What is the functional group of a carboxylic acid?1 mark
  2. What would you observe when a carboxylic acid is added to sodium carbonate powder?1 mark

7. Understanding Isomers

Isomers are compounds that share the same molecular formula but have different structural formulae. This means they have the same number and type of atoms, but the atoms are arranged differently. A simple example is C₄H₁₀, which can be the straight-chain molecule butane, or the branched-chain molecule methylpropane. Because their structures are different, isomers are different compounds with different physical properties, such as boiling points.

Key term

Isomers: Compounds with the same molecular formula but different arrangements of atoms in space (different structural formulae).

Examiner insight

When asked to draw isomers, make sure your structures are genuinely different and not just the same molecule rotated or flipped on the page. A good check is to try and name them; if they have different systematic names, they are different isomers.

Fun fact

The difference between the taste of oranges and lemons is largely due to two isomers of a molecule called limonene. One isomer smells of oranges, the other of lemons!

Worked example 12 marks

The molecular formula for an alcohol is C₃H₈O. Draw the displayed formulae for two isomers with this formula.

  1. 1
    1. Isomers have the same molecular formula but different structures. We need to arrange 3 carbons, 8 hydrogens and 1 oxygen in two different ways.
  2. 2
    1. Isomer 1 (Propan-1-ol): Arrange the 3 carbons in a chain (C-C-C). Place the -OH group on an end carbon (carbon 1).
  3. 3
    1. Fill in the remaining bonds with hydrogen atoms, ensuring each carbon has 4 bonds. The structure is CH₃-CH₂-CH₂-OH.
  4. 4
    1. Isomer 2 (Propan-2-ol): Arrange the 3 carbons in a chain (C-C-C). This time, place the -OH group on the middle carbon (carbon 2).
  5. 5
    1. Fill in the remaining bonds with hydrogen atoms. The structure is CH₃-CH(OH)-CH₃.
  6. 6
    1. Both structures have the formula C₃H₈O but are different compounds with different names and properties.

Recap

  • Isomers have the same molecular formula.
  • Isomers have different structural formulae (different arrangements of atoms).
  • Because their structures are different, isomers have different physical properties.
  • To draw isomers, rearrange the carbon skeleton or change the position of the functional group.

Quick check

  1. Do methane (CH₄), ethane (C₂H₆), or propane (C₃H₈) have any isomers?1 mark

End-of-chapter exercise

Test yourself on the whole chapter. Work through these before moving on.

  1. Define the term 'hydrocarbon'.1 mark
  2. Name the alkane with 3 carbon atoms and write its molecular formula.2 marks
  3. Butane has the molecular formula C₄H₁₀. Draw the displayed formulae of two isomers of butane.2 marks
  4. Ethene (C₂H₄) is an unsaturated hydrocarbon. Describe a chemical test to show that ethene is unsaturated, stating the expected observation.3 marks
  5. Write a balanced chemical equation, including state symbols, for the complete combustion of liquid ethanol (C₂H₅OH).3 marks
  6. Ethanoic acid is described as a weak acid. Explain the meaning of the term 'weak acid' with reference to ethanoic acid, including an equation.3 marks
  7. A compound X is a member of the alcohol homologous series and has a relative molecular mass of 74.0. (Relative atomic masses: C=12.0, H=1.0, O=16.0). Deduce the molecular formula of compound X.4 marks
  8. Propanoic acid (C₂H₅COOH) reacts with solid sodium carbonate. (a) State one observation you would make during this reaction. (b) Write a balanced chemical equation for this reaction.3 marks
  9. State two general characteristics of a homologous series.2 marks
  10. Ethanol (C₂H₅OH) reacts with ethanoic acid (CH₃COOH) in the presence of an acid catalyst to form an ester. (a) Name the ester formed. (b) Draw the full displayed formula of the ester formed.3 marks

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