How does the structure of organic molecules determine their reactions?
Classify organic functional groups and describe their characteristic reactions
Hydrocarbon families and functional groups, IUPAC naming, isomerism, and the characteristic reactions of alkanes, alkenes, alcohols, acids and esters.
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What this dot point is asking
Organic chemistry is the study of carbon compounds. Carbon forms four covalent bonds and can link into chains, branches and rings, giving an enormous variety of molecules. Compounds are organised into families called homologous series, where each member differs from the next by a unit and shares the same general formula and similar chemical properties, with a gradual change in physical properties such as boiling point.
The functional group is the reactive part of a molecule and determines its chemistry. Alkanes contain only single carbon-carbon bonds and are saturated. Alkenes contain a carbon-carbon double bond and are unsaturated. Other key families include haloalkanes (a halogen atom), alcohols (the hydroxyl group ), carboxylic acids (the group), and esters (the linkage). Knowing the functional group lets you predict both the name and the reactions.
IUPAC naming follows a systematic set of rules. Identify the longest carbon chain containing the functional group to give the stem (meth, eth, prop, but, pent and so on). The suffix indicates the family: -ane for alkanes, -ene for alkenes, -ol for alcohols, and -oic acid for carboxylic acids. Number the chain to give the functional group the lowest possible locant, and name branches as prefixes with their position numbers. For example, is propan-2-ol.
Isomerism arises because the same molecular formula can give different structures. Structural isomers differ in the connectivity of atoms, such as a straight chain versus a branched chain, or different positions of a functional group. Isomers can have markedly different physical and chemical properties despite sharing a molecular formula.
Each family has characteristic reactions. Alkanes are relatively unreactive but undergo substitution with halogens in the presence of ultraviolet light, where a hydrogen atom is replaced by a halogen atom. They also undergo complete combustion to give carbon dioxide and water, releasing large amounts of energy.
Alkenes are much more reactive because of the double bond. They undergo addition reactions, where atoms add across the double bond and it becomes a single bond. Examples include hydrogenation (adding with a catalyst), halogenation (adding , which decolourises bromine water and is a common test for unsaturation), and hydration (adding water to form an alcohol).
Alcohols undergo several important reactions. Primary and secondary alcohols can be oxidised by oxidants such as acidified potassium permanganate or acidified potassium dichromate. A primary alcohol oxidises first to an aldehyde and then to a carboxylic acid, while a secondary alcohol oxidises to a ketone. Tertiary alcohols resist oxidation because the carbon bearing the hydroxyl group has no hydrogen to remove. Alcohols also undergo combustion and dehydration to form alkenes.
Carboxylic acids are weak acids that react with bases and carbonates in the usual acid reactions. They also react with alcohols in an esterification (condensation) reaction, catalysed by concentrated sulfuric acid, to produce an ester and water. Esters often have pleasant fruity smells and are used as flavourings and fragrances.
In exams, draw structures clearly, name compounds using correct IUPAC rules with locants, and link each reaction type to the functional group present.
Exam-style practice questions
Practice questions written in the style of TASC exam questions on this dot point, with worked answer explainers. The year tag is the paper they imitate, not the source.
2023 TASC6 marksButanoic acid and butan-1-ol react with sodium. Identify the products of these two reactions. A student predicted: the balloon will inflate more for the reaction between butanoic acid and sodium than for butan-1-ol and sodium, due to the presence of more hydrogen atoms on the butanoic acid molecule. Evaluate this prediction.Show worked answer β
Products (2 marks). Sodium reacts with the acidic O-H of both compounds, releasing hydrogen gas. Butanoic acid: 2CH3CH2CH2COOH + 2Na -> 2CH3CH2CH2COO-Na+ (sodium butanoate) + H2. Butan-1-ol: 2CH3CH2CH2CH2OH + 2Na -> 2CH3CH2CH2CH2O-Na+ (sodium butoxide) + H2. The gas in both cases is H2.
Evaluation (4 marks). The prediction is incorrect in its reasoning. The amount of H2 produced depends only on the number of O-H (acidic) hydrogens that react with sodium, not on the total number of hydrogen atoms. Both molecules have exactly one O-H group, so equal moles of each would release the same amount of H2. Since equal masses of sodium (the limiting reagent, with the alcohols/acid in excess) are used, the amount of H2 is set by the sodium, so the two balloons would inflate to the same extent. The C-H hydrogens do not react with sodium.
2021 TASC2 marksPure ethanal is best made by converting ethanol to ethanal using a copper catalyst rather than using acidified potassium dichromate. Explain.Show worked answer β
Ethanal is an aldehyde, the partial-oxidation product of the primary alcohol ethanol.
With acidified potassium dichromate (a strong oxidiser) under reflux, the aldehyde is readily oxidised further to ethanoic acid (a carboxylic acid), so the product would be contaminated with acid and it is hard to stop at the aldehyde.
Using a heated copper catalyst carries out a milder oxidation (dehydrogenation) that converts ethanol to ethanal without over-oxidising it to the acid, so a purer sample of ethanal is obtained. (2 marks: dichromate over-oxidises to the acid; copper gives a controlled stop at the aldehyde.)
2021 TASC2 marksPropan-1-ol and propan-1-amine are both very soluble in water. Explain how the presence of the functional groups contributes to this property.Show worked answer β
Both molecules have a small hydrocarbon chain and a polar functional group that can hydrogen bond with water.
Propan-1-ol has a hydroxyl (-OH) group; propan-1-amine has an amine (-NH2) group. Both the O-H and N-H bonds are polar, with electronegative O or N atoms bearing lone pairs, so these groups form hydrogen bonds with water molecules.
Because the polar group can hydrogen bond extensively with water and the carbon chain is short (only three carbons), the molecules dissolve readily; the energy released forming solute-water hydrogen bonds offsets the disruption of water-water bonding. (2 marks: identify the H-bonding functional groups and link to solubility.)