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Alkanes, alkenes and alkynes explained: HSC Chemistry Module 7

Syllabus dot point

“Investigate the structural formulae, properties and reactions of alkanes, alkenes and alkynes, including combustion and addition reactions of alkenes”

11 min read

Quick answer

Alkanes are unreactive saturated CnH2n+2C_nH_{2n+2} molecules that only substitute under UV, alkenes (CnH2nC_nH_{2n}) and alkynes (CnH2n−2C_nH_{2n-2}) have reactive π\pi bonds that undergo addition with H2H_2, halogens, HXHX and water, and all three series combust to CO2CO_2 and H2OH_2O in excess oxygen.

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  1. What this dot point is asking
  2. The answer
  3. Examples in context
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  5. Exam-style questions
  6. Practice questions
In plain English

Think of the three hydrocarbon families as three types of handshake between carbon atoms. Alkanes only ever do a single, firm handshake (C−CC-C), so they are "fully booked" with hydrogens and chemically lazy, only reacting if you force the issue with UV light. Alkenes do a double handshake (C=CC=C), which is really one firm grip plus one loose, exposed grip (the pi bond) that anything electron-hungry, like bromine, can grab onto instantly, no UV needed. Alkynes go further with a triple handshake, two loose grips stacked on the one firm one, so they can react twice over, adding bromine or hydrogen not once but twice before becoming fully saturated. The bromine water test is just a colour-changing "unsaturation detector": if the orange-brown bromine disappears the instant you add it, there was a loose grip (a pi bond) ready to be grabbed; if the colour stays orange-brown in the dark, every handshake in that molecule was already firm and single.

What this dot point is asking

NESA wants you to distinguish alkanes, alkenes and alkynes by structure, predict and write equations for their characteristic reactions (combustion, addition, substitution), and explain why a C=CC=C bond makes alkenes much more reactive than alkanes. The dot point also covers the trends in physical properties down each series and the test that distinguishes saturated from unsaturated hydrocarbons.

The answer

Structural comparison

Series Bond type General formula Saturated? Example
Alkane C−CC-C single CnH2n+2C_nH_{2n+2} Yes CH3CH3CH_3CH_3 ethane
Alkene C=CC=C double CnH2nC_nH_{2n} No CH2=CH2CH_2=CH_2 ethene
Alkyne C≡CC \equiv C triple CnH2n−2C_nH_{2n-2} No HC≡CHHC \equiv CH ethyne

A double bond is one σ\sigma plus one π\pi bond; a triple bond is one σ\sigma plus two π\pi bonds. The π\pi electrons are loosely held and are the site of attack in addition reactions.

Physical properties

Across all three series, increasing chain length raises both melting point and boiling point because the dispersion forces between molecules grow with molecular size. C1 to C4 hydrocarbons are gases at room temperature, C5 to about C16 are liquids, and longer chains are waxy solids. All hydrocarbons are non-polar, immiscible with water, and float on water because their density is below 1 g/mL.

Comparing series at the same carbon number: an alkane and the corresponding alkene or alkyne have very similar boiling points, because the molecules differ only in two or four hydrogens. The double bond does not introduce significant polarity.

Combustion (all hydrocarbons)

Complete combustion (excess O2O_2) gives carbon dioxide and water. The general equation for any CxHyC_xH_y:

CxHy+(x+y4)O2→xCO2+y2H2OC_xH_y + \left(x + \frac{y}{4}\right)O_2 \rightarrow xCO_2 + \frac{y}{2}H_2O

Combustion is highly exothermic and is the basis for using hydrocarbons as fuels. For methane:

CH4(g)+2O2(g)→CO2(g)+2H2O(l)ΔH=−890 kJ/molCH_{4(g)} + 2O_{2(g)} \rightarrow CO_{2(g)} + 2H_2O_{(l)} \quad \Delta H = -890 \text{ kJ/mol}

Incomplete combustion (limited O2O_2) gives carbon monoxide COCO or soot CC plus water. Alkenes and alkynes burn with a sootier flame than alkanes because they have a higher carbon to hydrogen ratio, so less oxygen reaches the inner part of the flame.

Substitution reactions of alkanes

Alkanes are unreactive towards most reagents at room temperature. With halogens (chlorine or bromine) in UV light, they undergo free radical substitution:

CH4(g)+Cl2(g)→UVCH3Cl+HClCH_{4(g)} + Cl_{2(g)} \xrightarrow{UV} CH_3Cl + HCl

The mechanism has three steps: initiation (Cl2→2Cl⋅Cl_2 \rightarrow 2Cl \cdot under UV), propagation (Cl⋅+CH4→HCl+CH3⋅Cl \cdot + CH_4 \rightarrow HCl + CH_3 \cdot, then CH3⋅+Cl2→CH3Cl+Cl⋅CH_3 \cdot + Cl_2 \rightarrow CH_3Cl + Cl \cdot), and termination (radicals combine).

Addition reactions of alkenes

Addition reactions break the weaker π\pi bond and add two new groups across the former double bond, leaving a saturated product.

1. Hydrogenation (H₂, Ni catalyst, heat). Alkene plus hydrogen gives the corresponding alkane:

CH2=CH2(g)+H2(g)→Ni,150 degrees CCH3CH3(g)CH_2=CH_{2(g)} + H_{2(g)} \xrightarrow{Ni, 150 \text{ degrees C}} CH_3CH_{3(g)}

2. Halogenation (Br2Br_2 or Cl2Cl_2, room temperature, no catalyst). Alkene decolourises bromine water (orange-brown to clear) instantly. This is the standard test for unsaturation:

CH2=CH2(g)+Br2(aq)→CH2BrCH2BrCH_2=CH_{2(g)} + Br_{2(aq)} \rightarrow CH_2BrCH_2Br

3. Hydrohalogenation (HX, e.g. HCl or HBr). Alkene plus a hydrogen halide gives a haloalkane. Asymmetric alkenes follow Markovnikov's rule: H adds to the carbon already carrying more hydrogens, X adds to the more substituted carbon.

CH3CH=CH2+HBr→CH3CHBrCH3 (major)CH_3CH=CH_2 + HBr \rightarrow CH_3CHBrCH_3 \text{ (major)}

4. Hydration (H2OH_2O, dilute H2SO4H_2SO_4 catalyst, heat). Alkene plus water gives an alcohol. Markovnikov also applies.

CH2=CH2(g)+H2O(g)→H2SO4,300 degrees CCH3CH2OHCH_2=CH_{2(g)} + H_2O_{(g)} \xrightarrow{H_2SO_4, 300 \text{ degrees C}} CH_3CH_2OH

This is industrially how ethanol is made from ethene.

Reactions of alkynes

Alkynes undergo combustion and addition like alkenes, but each π\pi bond can be added across in turn. So ethyne plus excess bromine gives 1,1,2,2-tetrabromoethane:

HC≡CH+2Br2→CHBr2CHBr2HC \equiv CH + 2Br_2 \rightarrow CHBr_2CHBr_2

Ethyne C2H2C_2H_2 burns at very high temperatures with oxygen, which is why oxyacetylene torches are used for welding and metal cutting.

The bromine water test

To distinguish a saturated hydrocarbon (alkane) from an unsaturated one (alkene or alkyne), add a few drops of bromine water and shake.

  • Alkene or alkyne: orange-brown colour rapidly disappears (clear/colourless) due to addition.
  • Alkane: colour persists, unless exposed to UV light in which case it fades slowly with HBr fumes (substitution).

A second confirmatory test is acidified KMnO4KMnO_4: alkenes and alkynes decolourise purple permanganate at room temperature; alkanes do not react.

Reaction and test checkpoints
  • Bromine water test: instant decolourisation (orange-brown to colourless) = unsaturated (C=CC=C or C≡CC \equiv C present); colour persists in the dark = alkane (saturated).
  • General formulae: alkane CnH2n+2C_nH_{2n+2}, alkene CnH2nC_nH_{2n}, alkyne CnH2n−2C_nH_{2n-2}. Each series differs from the last by loss of 2 hydrogens (one more degree of unsaturation).
  • Substitution needs UV; addition does not. Alkanes only react with halogens under UV (free radical substitution); alkenes and alkynes react with halogens at room temperature in the dark (electrophilic addition).
  • Markovnikov's rule: for HXHX or H2OH_2O addition to an asymmetric alkene, H adds to the carbon already carrying more hydrogens ("the rich get richer").
  • Complete combustion, general form: CxHy+(x+y4)O2→xCO2+y2H2OC_xH_y + \left(x + \dfrac{y}{4}\right)O_2 \rightarrow xCO_2 + \dfrac{y}{2}H_2O.

An energy profile compares the activation energy pathway for alkane substitution (needs UV to overcome a high barrier) against alkene addition (a much lower barrier, reacting readily at room temperature):

Energy profile: alkane substitution vs alkene addition Two reaction energy profiles on the same axes. The alkane free radical substitution pathway has a tall activation energy barrier that requires UV light to overcome. The alkene electrophilic addition pathway has a much lower activation energy barrier and proceeds readily at room temperature. Both pathways are exothermic, with products lower in energy than reactants. high low Reaction progress Potential energy high Ea (needs UV) alkane + Cl2 (substitution) low Ea (room temp) alkene + Br2 (addition)

Worked classification and reaction examples

Worked example 1: classify and predict.

  • Compound: CH3CH2CH=CH2CH_3CH_2CH=CH_2 (but-1-ene).
  • Classification: contains one C=CC=C double bond, so it is an alkene, general formula CnH2nC_nH_{2n} (here C4H8C_4H_8).
  • Bromine water test prediction: instant decolourisation, orange-brown to colourless, because the pi bond of the double bond is attacked by Br2Br_2 in an electrophilic addition.
  • Balanced equation: CH3CH2CH=CH2(g)+Br2(aq)→CH3CH2CHBrCH2Br(l)CH_3CH_2CH=CH_{2(g)} + Br_{2(aq)} \rightarrow CH_3CH_2CHBrCH_2Br_{(l)}.

Marker's note: full marks require stating BOTH the classification reasoning (bond type, general formula) and the specific observation (colour change), not just the equation.

Worked example 2: Markovnikov addition of HBrHBr.

  • Compound: propene, CH3CH=CH2CH_3CH=CH_2, reacting with HBrHBr.
  • Step 1: identify the more substituted carbon of the double bond. C2C2 (the middle carbon) already bears one H and is attached to two other carbons' worth of substitution character in the transition state; by Markovnikov's rule the H of HBrHBr adds to the carbon with more hydrogens already, which is the terminal CH2CH_2 carbon (C1C1).
  • Step 2: BrBr adds to the other (more substituted) carbon, C2C2.
  • Major product: CH3CHBrCH3CH_3CHBrCH_3 (2-bromopropane).
  • Balanced equation: CH3CH=CH2(g)+HBr(g)→CH3CHBrCH3(l)CH_3CH=CH_{2(g)} + HBr_{(g)} \rightarrow CH_3CHBrCH_{3(l)}.

Marker's note: markers reward explicitly naming Markovnikov's rule and identifying which carbon has more hydrogens BEFORE stating the product; giving only the product without the reasoning risks losing a mark even if the structure drawn is correct.

Common traps
Confusing addition with substitution
Alkenes add (no atoms are lost); alkanes substitute (an H is replaced and HX is a byproduct). Different mechanisms, different conditions.
Forgetting the catalyst or conditions
Hydrogenation needs NiNi or PdPd catalyst and heat. Hydration needs dilute sulfuric acid and heat. Bromination of alkenes needs neither, only room temperature.
Markovnikov direction wrong
The H adds to the carbon with more Hs already. Think "the rich get richer" for H atoms.
Soot from incomplete combustion of alkanes
Alkanes generally burn cleanly; alkenes and alkynes are sootier. If asked to compare flames, mention the C:H ratio.
Writing a hydration product with the OH on the terminal carbon of a propene
Markovnikov puts OH on C2 of propene (giving propan-2-ol), not C1.
Exam technique for hydrocarbon questions

Always justify a classification with BOTH the bond type AND the general formula, e.g. "this is an alkene because it has one C=CC=C double bond, matching CnH2nC_nH_{2n}", not just "it's an alkene". For a bromine water test question, state the colour change AND the reason (pi bond attacked in electrophilic addition), since NESA markers give separate marks for observation and explanation. For any combustion or addition calculation, always show the balanced equation, the molar mass used, the mole ratio taken from the equation, and round your final answer to match the significant figures of the given data.

Examples in context

Example 1. Cracking at the Kurnell refinery (legacy operations). Until its 2014 conversion to an import terminal, Caltex's Kurnell refinery cracked long-chain alkanes from Bass Strait crude into shorter alkenes and alkanes for the petrol pool. Steam cracking ethane gave ethene plus hydrogen: C2H6→C2H4+H2C_2H_6 \rightarrow C_2H_4 + H_2. The ethene was the feedstock for the adjacent ethanol and polyethene units. Combustion of the residual fuel gas in the cracker furnace followed the standard alkane equation CxHy+(x+y/4)O2→xCO2+(y/2)H2OC_xH_y + (x + y/4)O_2 \rightarrow xCO_2 + (y/2)H_2O in excess oxygen. The HSC framework for combustion and addition reactions is the same chemistry the plant ran at industrial scale.

Example 2. Bromine water test in NSW HSC depth study. A school lab issued unlabelled samples of hexane and hex-1-ene asks students to identify them. Adding bromine water (orange-brown) to hex-1-ene gives instant decolourisation as the bromine adds across the double bond: CH2=CH(CH2)3CH3+Br2→CH2BrCHBr(CH2)3CH3CH_2=CH(CH_2)_3CH_3 + Br_2 \rightarrow CH_2BrCHBr(CH_2)_3CH_3. Hexane does not decolourise bromine water in the absence of UV. The contrast is the canonical HSC test for unsaturation. The same bromine number method is used at Hunter Valley wineries to measure unsaturated lipids in grape-seed oil and at Manildra to check ethanol purity for fuel-grade specifications.

Try this

Q1. State the general molecular formula for an alkane, an alkene and an alkyne, and give one observation that distinguishes an alkene from an alkane chemically. [3 marks]

  • Cue. Alkane CnH2n+2C_nH_{2n+2}, alkene CnH2nC_nH_{2n}, alkyne CnH2n−2C_nH_{2n-2}; alkene decolourises bromine water instantly without UV.

Q2. Write a balanced equation for the complete combustion of octane (C8H18C_8H_{18}) and calculate the volume of CO2CO_2 at 25 degrees C and 100 kPa produced from 5.00 g of octane (molar volume 24.79 L mol−1^{-1}). [3 marks]

  • Cue. C8H18+12.5O2→8CO2+9H2OC_8H_{18} + 12.5 O_2 \rightarrow 8 CO_2 + 9 H_2O; n(octane)=5.00/114.23=0.0438n(\text{octane}) = 5.00 / 114.23 = 0.0438; n(CO2)=0.350n(CO_2) = 0.350; V=0.350×24.79=8.69V = 0.350 \times 24.79 = 8.69 L.

Q3. But-1-ene reacts with HBr to give a major and minor product. (a) State Markovnikov's rule. (b) Identify the major product. (c) Explain why no second product forms with the alkane equivalent unless UV is supplied. [1+2+2 marks]

  • Cue. (a) H adds to the carbon with more H atoms. (b) 2-bromobutane (major). (c) Alkane requires free-radical substitution initiated by UV homolysis of Br2Br_2.

Exam-style questions

Questions in the style of NESA exam questions on this dot point, each with a worked answer. They are written by ExamExplained unless tagged "Past paper"; the year shows the paper a question is modelled on.

2021 HSC-style4 marks
Compare the reactivity of ethane and ethene by writing balanced equations for one reaction of each with bromine and explaining the difference in mechanism and observation.
Show worked answer →

A 4 mark answer needs two balanced equations, the mechanism labels, and the observational difference.

Ethane (alkane) with bromine. A substitution reaction that needs UV light to initiate.

C2H6(g)+Br2(g)→UVC2H5Br(l)+HBr(g)C_2H_{6(g)} + Br_{2(g)} \xrightarrow{UV} C_2H_5Br_{(l)} + HBr_{(g)}

Mechanism: free radical substitution. Slow without UV. Observation: brown bromine vapour fades slowly only when illuminated, and HBr fumes form.

Ethene (alkene) with bromine. An addition reaction across the C=CC=C double bond, occurring at room temperature in the dark.

C2H4(g)+Br2(aq)→C2H4Br2(l)C_2H_{4(g)} + Br_{2(aq)} \rightarrow C_2H_4Br_{2(l)}

Mechanism: electrophilic addition. Fast at room temperature. Observation: orange-brown bromine water is rapidly decolourised (clear).

Comparison. Ethene reacts much faster because the π\pi bond is electron-rich and attacks the electrophile Br2Br_2. Ethane has only C-H and C-C σ\sigma bonds, which are unreactive without high-energy UV initiation.

Markers reward (1) both balanced equations, (2) naming substitution vs addition, (3) the visual observation, (4) explaining why the π\pi bond drives the difference.

2018 HSC-style3 marks
Write a balanced equation for the complete combustion of propene (C₃H₆) and calculate the volume of CO₂ produced at 25°C and 100 kPa when 5.6 g of propene is fully combusted.
Show worked answer →

Step 1: Balanced equation.

2C3H6(g)+9O2(g)→6CO2(g)+6H2O(l)2C_3H_{6(g)} + 9O_{2(g)} \rightarrow 6CO_{2(g)} + 6H_2O_{(l)}

Or per mole of propene: C3H6+4.5O2→3CO2+3H2OC_3H_6 + 4.5 O_2 \rightarrow 3 CO_2 + 3 H_2O.

Step 2: Moles of propene. M(C3H6)=42.08M(C_3H_6) = 42.08 g/mol.

n(C3H6)=5.642.08=0.133 moln(C_3H_6) = \frac{5.6}{42.08} = 0.133 \text{ mol}

Step 3: Moles of CO2CO_2. Ratio 3:1.

n(CO2)=3×0.133=0.399 moln(CO_2) = 3 \times 0.133 = 0.399 \text{ mol}

Step 4: Volume at 25 degrees C, 100 kPa. Molar volume = 24.79 L/mol.

V=0.399×24.79=9.89 LV = 0.399 \times 24.79 = 9.89 \text{ L}

Markers reward (1) the balanced equation, (2) correct mole calculation, (3) correct molar volume at HSC standard conditions.

Practice questions

Original practice questions graded from foundation to exam level, each with a full worked solution. Try them before revealing the solution.

foundation3 marks
Classify each hydrocarbon as an alkane, alkene or alkyne and state the general formula that confirms your classification: (a) CH3CH2CH2CH3CH_3CH_2CH_2CH_3; (b) CH2=CHCH3CH_2=CHCH_3; (c) HC≡CCH3HC \equiv CCH_3.
Show worked solution →

A 3-mark classify question needs the correct family AND the matching general formula for each.

(a) CH3CH2CH2CH3CH_3CH_2CH_2CH_3 (butane)
All bonds are single C−CC-C bonds, so this is an alkane, matching CnH2n+2C_nH_{2n+2} (here C4H10C_4H_{10}).
(b) CH2=CHCH3CH_2=CHCH_3 (propene)
Contains one C=CC=C double bond, so this is an alkene, matching CnH2nC_nH_{2n} (here C3H6C_3H_6).
(c) HC≡CCH3HC \equiv CCH_3 (propyne)
Contains one C≡CC \equiv C triple bond, so this is an alkyne, matching CnH2n−2C_nH_{2n-2} (here C3H4C_3H_4).

Marking criteria: 1 mark per compound for correctly naming the family AND citing the matching general formula; family name alone without the formula reasoning earns partial credit only.

foundation3 marks
State the reagent, condition and observation for a test that distinguishes hex-1-ene from hexane, and explain the chemical reason for the difference.
Show worked solution →
Reagent and condition
Add a few drops of bromine water to each sample at room temperature, in the dark (no UV).
Observation
Hex-1-ene: the orange-brown bromine water is instantly decolourised (becomes colourless). Hexane: the orange-brown colour persists (no reaction).
Chemical reason
Hex-1-ene has a C=CC=C double bond, so it contains a reactive, electron-rich pi bond that undergoes electrophilic addition with Br2Br_2 at room temperature. Hexane has only C−CC-C and C−HC-H sigma bonds, which are unreactive towards Br2Br_2 without UV light to initiate free radical substitution.

Marking criteria: 1 mark for the correct reagent/condition, 1 mark for both observations stated correctly, 1 mark for the pi bond/electrophilic addition reasoning explaining the difference.

core5 marks
A student reacts 8.40 g of hex-1-ene (C6H12C_6H_{12}) with excess bromine water. Calculate the mass of bromine (Br2Br_2) theoretically consumed, to 3 significant figures. (M(C6H12)=84.16 g mol−1M(C_6H_{12}) = 84.16\ \text{g mol}^{-1}, M(Br2)=159.80 g mol−1M(Br_2) = 159.80\ \text{g mol}^{-1}.)
Show worked solution →

Step 1: write the balanced equation (1:1 stoichiometry).

CH2=CH(CH2)3CH3(l)+Br2(aq)→CH2BrCHBr(CH2)3CH3(l)CH_2=CH(CH_2)_3CH_{3(l)} + Br_{2(aq)} \rightarrow CH_2BrCHBr(CH_2)_3CH_{3(l)}

One mole of hex-1-ene reacts with one mole of Br2Br_2.

Step 2: moles of hex-1-ene.

n(C6H12)=mM=8.40 g84.16 g mol−1=0.09981 moln(C_6H_{12}) = \frac{m}{M} = \frac{8.40\ \text{g}}{84.16\ \text{g mol}^{-1}} = 0.09981\ \text{mol}

Step 3: moles of Br2Br_2 (1:1 ratio).

n(Br2)=0.09981 moln(Br_2) = 0.09981\ \text{mol}

Step 4: mass of Br2Br_2.

m=n×M=0.09981 mol×159.80 g mol−1=15.95 gm = n \times M = 0.09981\ \text{mol} \times 159.80\ \text{g mol}^{-1} = 15.95\ \text{g}

Step 5: round to 3 significant figures (matching 8.40 g, which has 3 s.f.).

m(Br2)=16.0 gm(Br_2) = 16.0\ \text{g}

Marking criteria: 1 mark for the correct balanced 1:1 equation, 1 mark for correct moles of hex-1-ene, 1 mark for correctly carrying the 1:1 mole ratio, 1 mark for the mass calculation, 1 mark for the correct final answer to 3 significant figures with units. This is a THEORETICAL value; a real bromine-water addition would need at least this much Br2Br_2 present for complete reaction.

core5 marks
The energy profile diagram above compares alkane free radical substitution with alkene electrophilic addition. (a) Identify which pathway has the higher activation energy and state one piece of evidence for this from the diagram. (b) Explain, in terms of bonding, why the two pathways have different activation energies. (c) State one experimental condition that must be supplied for the higher-Ea pathway to proceed at a useful rate.
Show worked solution →
(a) Identification and evidence
The alkane substitution pathway (alkane + Cl2Cl_2) has the higher activation energy. Evidence: its peak sits much closer to the "high" energy line on the diagram than the peak of the alkene addition (alkene + Br2Br_2) pathway, which peaks much lower, closer to the reactant energy level.
(b) Bonding explanation
Alkane substitution requires breaking a strong C−HC-H sigma bond and a Cl−ClCl-Cl sigma bond homolytically to generate radicals, which needs a large energy input, giving a high activation energy. Alkene addition only requires breaking the weaker, more exposed pi bond of the C=CC=C double bond, which has electron density above and below the bond axis and is far more accessible to an electrophile like Br2Br_2, so much less energy is needed to start the reaction.
(c) Condition required
UV light (to homolytically cleave Cl2Cl_2 into radicals and initiate the substitution mechanism).

Marking criteria: (a) 1 mark for correct pathway identified, 1 mark for evidence quoted from the diagram. (b) 2 marks for the bonding-based explanation (sigma vs pi bond strength/accessibility). (c) 1 mark for UV light (or equivalent high-energy initiation).

core6 marks
But-2-yne (CH3C≡CCH3CH_3C \equiv CCH_3) is fully hydrogenated to butane using excess hydrogen gas and a nickel catalyst. (a) Write a balanced equation for the full hydrogenation. (b) Calculate the volume of hydrogen gas, at 25 degrees C and 100 kPa, required to fully hydrogenate 2.16 g of but-2-yne, to 3 significant figures. (M(C4H6)=54.09 g mol−1M(C_4H_6) = 54.09\ \text{g mol}^{-1}, molar volume =24.79 L mol−1= 24.79\ \text{L mol}^{-1}.)
Show worked solution →

(a) Balanced equation. Each π\pi bond of the triple bond needs its own H2H_2 molecule, so full hydrogenation of a triple bond to a single bond needs 2 mol of H2H_2 per mole of alkyne.

CH3C≡CCH3(g)+2H2(g)→NiCH3CH2CH2CH3(g)CH_3C \equiv CCH_{3(g)} + 2H_{2(g)} \xrightarrow{Ni} CH_3CH_2CH_2CH_{3(g)}

(b) Step 1: moles of but-2-yne.

n(C4H6)=mM=2.16 g54.09 g mol−1=0.03993 moln(C_4H_6) = \frac{m}{M} = \frac{2.16\ \text{g}}{54.09\ \text{g mol}^{-1}} = 0.03993\ \text{mol}

Step 2: moles of H2H_2 (2:1 ratio from the equation).

n(H2)=2×0.03993 mol=0.07987 moln(H_2) = 2 \times 0.03993\ \text{mol} = 0.07987\ \text{mol}

Step 3: volume of H2H_2 at 25 degrees C, 100 kPa.

V=n×Vm=0.07987 mol×24.79 L mol−1=1.980 LV = n \times V_m = 0.07987\ \text{mol} \times 24.79\ \text{L mol}^{-1} = 1.980\ \text{L}

Step 4: round to 3 significant figures (matching 2.16 g).

V(H2)=1.98 LV(H_2) = 1.98\ \text{L}

Marking criteria: (a) 1 mark for the correctly balanced equation showing 2 mol H2H_2 per mole of alkyne, with the nickel catalyst condition. (b) 1 mark for correct moles of but-2-yne, 1 mark for correctly doubling to get moles of H2H_2 (recognising the triple bond needs two additions), 1 mark for the volume calculation, 1 mark for the final answer to 3 significant figures with units.

exam6 marks
Compare the reactivity of but-1-ene and butane towards bromine, addressing mechanism, conditions, rate and the practical test used to distinguish them, and explain your comparison using bonding concepts.
Show worked solution →

A 6-mark COMPARE needs both similarities/differences addressed across mechanism, conditions, rate and a named test, backed by bonding reasoning.

Band 6 plan.

  • Name both mechanisms: but-1-ene undergoes electrophilic addition; butane undergoes free radical substitution.
  • State conditions: but-1-ene reacts with bromine water at room temperature in the dark; butane requires UV light to react at all.
  • Compare rate: but-1-ene reacts instantly; butane reacts slowly even under UV, because the mechanism needs a three-step radical chain (initiation, propagation, termination) rather than a single electrophilic attack.
  • Name the distinguishing test: bromine water, decolourised instantly by but-1-ene, unaffected (in the dark) by butane.
  • Bonding reasoning: but-1-ene's C=CC=C double bond has an exposed, electron-rich pi bond that directly attracts the electrophilic Br2Br_2 molecule; butane has only strong, unreactive C−HC-H and C−CC-C sigma bonds that require UV photons to homolytically cleave ClCl-ClCl/BrBr-BrBr bonds before any reaction can begin.

Model answer (excerpt). But-1-ene and butane react with bromine by fundamentally different mechanisms. But-1-ene undergoes electrophilic addition: the electron-rich pi bond of its C=CC=C double bond attacks Br2Br_2, forming 1,2-dibromobutane, and this proceeds instantly at room temperature in bromine water, decolourising it from orange-brown to colourless. Butane, lacking any pi bond, reacts only by free radical substitution, and only when UV light is supplied to homolyse Br2Br_2 into radicals; even then the reaction is comparatively slow, since it proceeds through a three-stage radical chain mechanism (initiation, propagation, termination) rather than a single-step electrophilic attack. This difference is exploited directly as the standard laboratory test for unsaturation: instant decolourisation of bromine water identifies an alkene (or alkyne), while a lack of colour change in the dark identifies a saturated alkane.

Marker's note: top-band answers (1) correctly name BOTH mechanisms, (2) state the conditions for both including the UV requirement, (3) explicitly compare rate, not just describe each separately, (4) name bromine water as the confirmatory test, and (5) tie the whole comparison back to the presence or absence of an exposed pi bond. Answers that describe only one hydrocarbon in detail without a direct comparison are capped at half marks.

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