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Ethane reacts with chlorine to form chloroethane - CIE - A-Level Chemistry - Question 3 - 2015 - Paper 1

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Ethane reacts with chlorine to form chloroethane. C2H6(g) + Cl2(g) → C2H5Cl(g) + HCl(g) a) Use bond energies from the Data Booklet to calculate the enthalpy change... show full transcript

Worked Solution & Example Answer:Ethane reacts with chlorine to form chloroethane - CIE - A-Level Chemistry - Question 3 - 2015 - Paper 1

Step 1

Use bond energies from the Data Booklet to calculate the enthalpy change for this reaction. Include a sign in your answer.

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Answer

To calculate the enthalpy change for the reaction, we need to consider the bond energies involved:

  1. Bond Breaking:

    • Bond breaking involves the following bonds:

      • C–H bonds in ethane (C2H6): 6 bonds at 410 kJ each.
      • Cl–Cl bond: 1 bond at 242 kJ.
    • Total energy for bond breaking is:

      extEnergyforbreaking=(6imes410)+242=2460+242=2702extkJ ext{Energy for breaking} = (6 imes 410) + 242 = 2460 + 242 = 2702 ext{ kJ}

  2. Bond Forming:

    • Forming bonds involves:

      • C–Cl bond in chloroethane (C2H5Cl): 1 bond at 340 kJ.
      • H–Cl bond: 1 bond at 431 kJ.
    • Total energy for bond forming is:

      extEnergyforforming=340+431=771extkJ ext{Energy for forming} = 340 + 431 = 771 ext{ kJ}

  3. **Enthalpy Change:
    extEnthalpychange=extTotalenergytobreakbondsextTotalenergytoformbondsext{Enthalpy change} = ext{Total energy to break bonds} - ext{Total energy to form bonds} =2702771=1931extkJ= 2702 - 771 = 1931 ext{ kJ}

    • Therefore, the enthalpy change for the reaction is +1931 kJ mol⁻¹.

Step 2

State the conditions needed for this reaction to occur.

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Answer

The reaction between ethane and chlorine requires specific conditions, which are:

  • UV light or high temperature / sunlight to initiate the reaction.

Step 3

Use a series of equations to describe the mechanism of this reaction including the names of each stage and an indication of how butane can be produced as a minor by-product.

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Answer

The reaction mechanism can be divided into three stages:

  1. Initiation:
    • Chlorine molecules (Cl2) dissociate into two chlorine radicals (Cl·):

ightarrow 2 ext{Cl}^{ullet}$$

  1. Propagation:
    • A chlorine radical abstracts a hydrogen atom from ethane, forming chloroethane and a second chlorine radical:

ightarrow ext{C}_2 ext{H}_5 ext{Cl} + ext{H}^{ullet}$$

  • The newly formed radical can react with another chlorine molecule to regenerate chlorine radicals:

ightarrow ext{C}_2 ext{H}_5 ext{Cl} + ext{Cl}^{ullet}$$

  • Minor by-product: Butane can be produced if the hydrogen atom abstracted comes from another ethyl radical:

ightarrow ext{C}4 ext{H}{10}$$

  1. Termination:
    • All radicals combine to end the chain reaction, e.g.,

ightarrow ext{Cl}_2 ext{C}_2 ext{H}_5^{ullet} + ext{H}^{ullet} ightarrow ext{C}_2 ext{H}_6$$.

Step 4

Give the name of X.

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Answer

The name of the intermediate compound X is ethene.

Step 5

Suggest the reagent and conditions needed for reaction 1.

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Answer

The reagent for reaction 1 is KOH or NaOH, and the conditions required are ethanol as the solvent and heat under reflux.

Step 6

Suggest the reagent and conditions needed for reaction 2.

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Answer

For reaction 2, the reagent is H2 along with a catalyst such as Pt (platinum) or Ni (nickel).

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