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CH4(g) + Cl(g) -> CH3(g) + HCl(g) dH° = -14 kJ/mol_rxn NH3(g) + Cl(g) -> NH2(g) + HCl(g) dH° = -36 kBonding Chemistry Question

Question

CH4(g) + Cl(g) → CH3(g) + HCl(g) dH° = -14 kJ/mol_rxn
NH3(g) + Cl(g) → NH2(g) + HCl(g) dH° = -36 kJ/mol_rxn
H2O(g) + Cl(g) → OH(g) + HCl(g) dH° = +40 kJ/mol_rxn

Based on the data above, what can be concluded regarding the strength of the C-H, N-H, and O-H bonds in the molecules shown?

A.

The C-H bond is the strongest.

B.

The N-H bond is the strongest.

C.

The O-H bond is the strongest.

✓ Correct
D.

Nothing can be concluded without knowing the strength of the H-Cl bond.

💡 Solution & Explanation

STEPS:

1. Understand the relationship between reaction enthalpy and bond energy:
The standard enthalpy change of a reaction (ΔH\Delta H^\circ) can be estimated by calculating the difference between the energy required to break bonds in the reactants and the energy released when new bonds are formed in the products:
ΔH=Bond Energies of Broken BondsBond Energies of Formed Bonds\Delta H^\circ = \sum \text{Bond Energies of Broken Bonds} - \sum \text{Bond Energies of Formed Bonds}

2. Analyze the bonds broken and formed in each given reaction:
For all three gas-phase reactions, a chlorine atom (Cl\text{Cl}) abstracts a hydrogen atom from a gaseous reactant to form a gaseous hydrogen chloride (HCl\text{HCl}) molecule.
* In Reaction 1, one C–H\text{C–H} bond in CH4\text{CH}_4 is broken, and one H–Cl\text{H–Cl} bond is formed.
* In Reaction 2, one N–H\text{N–H} bond in NH3\text{NH}_3 is broken, and one H–Cl\text{H–Cl} bond is formed.
* In Reaction 3, one O–H\text{O–H} bond in H2O\text{H}_2\text{O} is broken, and one H–Cl\text{H–Cl} bond is formed.

3. Express the enthalpy change of each reaction mathematically using bond dissociation energies (DD):
* Reaction 1: ΔH1=D(C–H)D(H–Cl)=14 kJ/molrxn\Delta H^\circ_1 = D(\text{C–H}) - D(\text{H–Cl}) = -14\text{ kJ/mol}_{\text{rxn}}
* Reaction 2: ΔH2=D(N–H)D(H–Cl)=36 kJ/molrxn\Delta H^\circ_2 = D(\text{N–H}) - D(\text{H–Cl}) = -36\text{ kJ/mol}_{\text{rxn}}
* Reaction 3: ΔH3=D(O–H)D(H–Cl)=+40 kJ/molrxn\Delta H^\circ_3 = D(\text{O–H}) - D(\text{H–Cl}) = +40\text{ kJ/mol}_{\text{rxn}}

4. Isolate and compare the relative bond strengths relative to the shared D(H–Cl)D(\text{H–Cl}) term:
By rearranging the equations to solve for the individual bond dissociation energies, we can see how they compare:
* D(C–H)=D(H–Cl)14 kJ/molD(\text{C–H}) = D(\text{H–Cl}) - 14\text{ kJ/mol}
* D(N–H)=D(H–Cl)36 kJ/molD(\text{N–H}) = D(\text{H–Cl}) - 36\text{ kJ/mol}
* D(O–H)=D(H–Cl)+40 kJ/molD(\text{O–H}) = D(\text{H–Cl}) + 40\text{ kJ/mol}

5. Conclude which bond is the strongest:
Because D(H–Cl)D(\text{H–Cl}) is a constant value, we can rank the bond energies directly:
D(O–H)>D(C–H)>D(N–H)D(\text{O–H}) > D(\text{C–H}) > D(\text{N–H})
* Breaking the O–H\text{O–H} bond requires 40 kJ/mol40\text{ kJ/mol} *more* energy than is released by forming the H–Cl\text{H–Cl} bond, making this process endothermic.
* Breaking the C–H\text{C–H} and N–H\text{N–H} bonds requires *less* energy than is released by forming the H–Cl\text{H–Cl} bond, making these processes exothermic.
* Therefore, the O–H\text{O–H} bond is the strongest bond among those shown, which makes Option C the correct answer.

*

WHY_OTHERS_WRONG:

  • Option A is incorrect: The C–H\text{C–H} bond is weaker than the O–H\text{O–H} bond. The reaction involving the cleavage of the C–H\text{C–H} bond is exothermic (ΔH=14 kJ/molrxn\Delta H^\circ = -14\text{ kJ/mol}_{\text{rxn}}), indicating that the C–H\text{C–H} bond is easier to break than the O–H\text{O–H} bond (which is endothermic at ΔH=+40 kJ/molrxn\Delta H^\circ = +40\text{ kJ/mol}_{\text{rxn}}).
  • Option B is incorrect: The N–H\text{N–H} bond is the weakest of the three bonds. Its cleavage reaction is the most exothermic (ΔH=36 kJ/molrxn\Delta H^\circ = -36\text{ kJ/mol}_{\text{rxn}}), which means it requires the least amount of energy input to break.
  • Option D is incorrect: While the absolute values of the bond energies cannot be calculated without knowing the exact value of the H–Cl\text{H–Cl} bond energy, we can easily determine their relative strengths. Because D(H–Cl)D(\text{H–Cl}) is a constant, comparing the ΔH\Delta H^\circ values allows us to establish a definitive comparative ranking.
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