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How do chemists name, classify and represent organic molecules, and what is isomerism?

Functional groups and homologous series, IUPAC nomenclature, empirical, molecular, structural, displayed and skeletal formulae, general formulae, and structural and stereoisomerism.

An Eduqas A-Level Chemistry C3.1 answer on functional groups and homologous series, IUPAC naming, types of formula, general formulae, and structural and stereoisomerism.

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  1. What this topic is asking
  2. Functional groups and homologous series
  3. IUPAC nomenclature
  4. Representing molecules
  5. Structural isomerism
  6. Stereoisomerism (introduction)
  7. Examples in context
  8. Try this

What this topic is asking

Eduqas topic C3.1 covers the language of organic chemistry: functional groups and homologous series, IUPAC nomenclature, the various ways of representing molecules, general formulae, and the meaning of isomerism. It is the grammar that every later organic topic depends on.

Functional groups and homologous series

Members of a series have similar chemical properties because they share a functional group, and a smooth gradation in physical properties (such as boiling point) because the chain length changes.

IUPAC nomenclature

The systematic name has three parts: a stem for the longest carbon chain (meth, eth, prop, but, pent...), a suffix for the principal functional group (-ane, -ene, -ol, -al, -one, -oic acid), and prefixes for substituents (chloro-, methyl-) with locant numbers. Number the chain from the end that gives the functional group, then the substituents, the lowest possible numbers.

Representing molecules

Structural isomerism

Stereoisomerism (introduction)

Stereoisomers have the same structural formula but a different spatial arrangement. E/ZE/Z (geometric) isomerism arises from restricted rotation about a C=C\text{C=C} double bond, and optical isomerism arises from a chiral carbon. The full treatment is in the Organic Chemistry and Analysis section; here you only need to recognise the categories.

Examples in context

Example 1. Why isomers matter in pharmacology. Two structural isomers can have completely different properties; for example, ethanol (a drinkable alcohol) and dimethyl ether (a gas) share the formula C2H6O\text{C}_2\text{H}_6\text{O} but behave entirely differently because of their different functional groups.

Example 2. Skeletal formulae in research. Chemists draw complex natural products as skeletal formulae because displaying every C and H would be unreadable; the convention lets a reader see the functional groups and ring systems at a glance.

Try this

Q1. Give the general formula of the alkenes and use it to deduce the molecular formula of the alkene with six carbon atoms. [1 mark]

  • Cue. CnH2n\text{C}_n\text{H}_{2n}; for n=6n = 6, C6H12\text{C}_6\text{H}_{12}.

Q2. Name the compound CH3CH2CH2COOH\text{CH}_3\text{CH}_2\text{CH}_2\text{COOH}. [1 mark]

  • Cue. Butanoic acid (a four-carbon carboxylic acid).

Exam-style practice questions

Practice questions written in the style of WJEC Eduqas exam questions on this dot point, with worked answer explainers. The year tag is the paper they imitate, not the source.

Eduqas 20184 marksA hydrocarbon has the molecular formula C4H8\text{C}_4\text{H}_8. (a) Draw the displayed formulae and give the names of two chain isomers that are alkenes. (b) Explain why these are described as structural isomers.
Show worked answer β†’

(a) But-1-ene, CH2=CH-CH2-CH3\text{CH}_2=\text{CH-CH}_2\text{-CH}_3, and but-2-ene, CH3-CH=CH-CH3\text{CH}_3\text{-CH}=\text{CH-CH}_3 (or methylpropene). Award 1 mark for each correct displayed formula and name (2).

(b) They have the same molecular formula (C4H8\text{C}_4\text{H}_8) but different structural formulae, because the position of the double bond (or the carbon skeleton) differs (2).

Eduqas 20213 marks(a) Name the compound CH3CH(CH3)CH2OH\text{CH}_3\text{CH(CH}_3)\text{CH}_2\text{OH}. (b) State the general formula of the alcohols and use it to give the molecular formula of the alcohol with five carbon atoms.
Show worked answer β†’

(a) 2-methylpropan-1-ol (1).

(b) The general formula of the alcohols is CnH2n+1OH\text{C}_n\text{H}_{2n+1}\text{OH} (or CnH2n+2O\text{C}_n\text{H}_{2n+2}\text{O}) (1). For n=5n = 5: C5H11OH\text{C}_5\text{H}_{11}\text{OH}, i.e. C5H12O\text{C}_5\text{H}_{12}\text{O} (1).

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