Hydrocarbons: Question 7

Syllabus 14.2

Structured AS 7 marks

But-2-ene, CH3CH=CHCH3\text{CH}_3\text{CH}=\text{CHCH}_3, is an unsaturated hydrocarbon that can be converted into butane by hydrogenation.

(a) Identify the type of reaction that converts but-2-ene into butane, and state the reagent and conditions required. [3]

(b) Write a balanced equation for this reaction. [1]

(c) Give one industrial application of the hydrogenation of carbon-carbon double bonds in unsaturated compounds. [1]

(d) Explain, in terms of bonding, why but-2-ene can undergo this reaction but butane cannot react further with hydrogen. [2]

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Worked solution

Part (a): Identifying the reaction, reagent and conditions

Converting but-2-ene into butane is an addition reaction, specifically hydrogenation: hydrogen atoms add across the C=C double bond. The reagent required is hydrogen gas, H2\text{H}_2, and the reaction needs a nickel catalyst (platinum or palladium would also work) at a temperature of around 150°C.

Part (b): The equation

CH3CH=CHCH3+H2Ni, 150°CCH3CH2CH2CH3\text{CH}_3\text{CH}=\text{CHCH}_3 + \text{H}_2 \xrightarrow{\text{Ni, } 150°\text{C}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3

Check (atom balance): C: 4=44=4. H: 8+2=108+2=10 on the left; C4H10\text{C}_4\text{H}_{10} has 1010 hydrogen atoms on the right. Both balance.

Part (c): Industrial application

Hydrogenation of C=C double bonds is used industrially to convert unsaturated liquid vegetable oils (which contain several C=C double bonds) into saturated, solid or semi-solid fats, for example, in the manufacture of margarine from vegetable oil.

Part (d): Why but-2-ene reacts further but butane does not

But-2-ene contains a reactive carbon-carbon double bond: one of the two bonds joining these carbons (the π\pi bond) has electron density exposed above and below the plane of the molecule, making it available to react with an added atom on each carbon. Butane, in contrast, is fully saturated. Every carbon is already bonded to four other atoms by strong single (σ\sigma) bonds only, with no π\pi bond present, so there is no multiple bond across which further atoms could add.

Final answers

  • (a) Addition (hydrogenation); reagent H2\text{H}_2; nickel catalyst, around 150°C.
  • (b) CH3CH=CHCH3+H2CH3CH2CH2CH3\text{CH}_3\text{CH}=\text{CHCH}_3 + \text{H}_2 \rightarrow \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3
  • (c) Hardening of unsaturated vegetable oils into margarine (or an equivalent solid-fat example).
  • (d) But-2-ene has a reactive π\pi bond available for addition; butane has only single bonds and is fully saturated, so it cannot react further with hydrogen.