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A \(C-F\) bond energy can be computed from thermochemical studies of the vapor- phase reaction $$ \mathrm{CH}_{4}+4 \mathrm{~F}_{2} \rightarrow \mathrm{CF}_{4}+4 \mathrm{HF} \quad \Delta H^{0}=-460 \mathrm{kcal} $$ Show how the \(\Delta H^{0}\) value for this reaction may be used to calculate the energy of the \(\mathrm{C}-\mathrm{F}\) bond if all the other bond energies are known.

Short Answer

Expert verified
The C-F bond energy is 114 kcal/mol.

Step by step solution

01

Identify Known Bond Energies

We need to first identify all the known bond energies in the molecules involved. For methane (\( \mathrm{CH}_4 \)), we have four C-H bonds. For fluorine (\( \mathrm{F}_2 \)), there are four F-F bonds. In tetrafluoromethane (\( \mathrm{CF}_4 \)), there are four C-F bonds, and in hydrogen fluoride (\( \mathrm{HF} \)), there are four H-F bonds.
02

Write the Equation for Reaction Enthalpy

We express the reaction enthalpy, \( \Delta H^0 \), in terms of bond enthalpies. \[ \Delta H^0 = \sum (\text{Bond Energies of Reactants}) - \sum (\text{Bond Energies of Products}) \] So, \( \Delta H^0 = (4E_{\mathrm{C-H}} + 4E_{\mathrm{F-F}}) - (4E_{\mathrm{C-F}} + 4E_{\mathrm{H-F}}) \).
03

Solve for C-F Bond Energy

Rearrange the equation from Step 2 to solve for the C-F bond energy, \( E_{\mathrm{C-F}} \). \[ 4E_{\mathrm{C-F}} = 4E_{\mathrm{C-H}} + 4E_{\mathrm{F-F}} - 4E_{\mathrm{H-F}} - \Delta H^0 \] \[ E_{\mathrm{C-F}} = \frac{4E_{\mathrm{C-H}} + 4E_{\mathrm{F-F}} - 4E_{\mathrm{H-F}} - \Delta H^0}{4} \]
04

Substitute Known Values

We substitute the known bond energies into the equation: \( E_{\mathrm{C-H}} = 99 \mathrm{kcal/mol} \), \( E_{\mathrm{F-F}} = 36 \mathrm{kcal/mol} \), \( E_{\mathrm{H-F}} = 136 \mathrm{kcal/mol} \), and \( \Delta H^0 = -460 \mathrm{kcal} \). Now calculate \( E_{\mathrm{C-F}} \). \[ E_{\mathrm{C-F}} = \frac{4 \times 99 + 4 \times 36 - 4 \times 136 - (-460)}{4} \]
05

Perform the Calculation

Calculate the energy value: \( E_{\mathrm{C-F}} = \frac{396 + 144 - 544 + 460}{4} = \frac{456}{4} = 114 \mathrm{kcal/mol} \).

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Thermochemical Calculations
Thermochemical calculations are a crucial tool in chemistry used to determine the heat exchange associated with chemical reactions. This concept is particularly useful for evaluating reaction enthalpies and bond energies. When reacting substances, atoms and molecules undergo reconfiguration, often requiring or releasing energy. The calculation of this energy is fundamental to predicting reaction behavior.

To perform thermochemical calculations, you should understand the principles of energy conservation and explicitly determine the enthalpy change, denoted as \( \Delta H^0 \).
  • It involves calculating the balance between the energy of bonds broken in reactants and formed in products.
  • Subtract the sum of bond energies of products from those of reactants, leading to the equation: \( \Delta H^0 = \sum(\text{Bond Energies of Reactants}) - \sum(\text{Bond Energies of Products}) \).
  • Remember that enthalpy is typically measured in kilocalories per mole or kilojoules per mole.
Understanding and applying these principles can be effortlessly done with consistent practice and familiarization with the bond energies involved.
Bond Enthalpy
Bond enthalpy, also known as bond dissociation energy, is a measure of the strength of a chemical bond. It represents the amount of energy required to break one mole of a specific bond in a gaseous substance.
  • The bond enthalpy values are typically averages derived from experiments on similar compounds.
  • These values are essential for predicting the stability of molecules and the energy change in chemical reactions.
  • Factors influencing bond enthalpy include the type of bonded atoms and their electronegativity, as well as the bond length.
For the given exercise, bond enthalpy information helps in calculating specific bond energies like that for the \( \text{C-F} \) bond.Consider the sample calculation in the solution steps:- Given bond energies for \( \text{C-H} \), \( \text{F-F} \), and \( \text{H-F} \).- Use these known values and reaction enthalpy to solve for the unknown \( \text{C-F} \) bond enthalpy.

This systematic approach ensures accurate calculation of bond energies using enthalpy data from known reactions and compounds.
Reaction Enthalpy
Reaction enthalpy is the overall enthalpic change during a chemical reaction, providing insight into the energy dynamics of the process. It can indicate whether a reaction is exothermic (releases energy) or endothermic (absorbs energy).

An exothermic reaction, like the one in the exercise with \( \Delta H^0 = -460 \text{kcal/mol} \), releases energy, thus having a negative \( \Delta H^0 \). In contrast, a positive \( \Delta H^0 \) suggests an endothermic nature.
  • Understanding this change is vital for calculating reaction feasibility and designing energy-efficient processes.
  • The reaction enthalpy also helps in determining how bond energies transform during chemical changes.
  • To compute a specific bond energy from reaction enthalpy, manipulate the equation to highlight the desired unknown value.
In chemical synthesis and industrial applications, reaction enthalpy guides decisions on reaction conditions and optimization.

This concept, structured around bond energy contribution, forms the basis for more advanced studies and practical applications in thermochemistry.

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Most popular questions from this chapter

Knowing that the equilibrium constant \(K_{\text {eq for formation of nonane from solid carbon and hydrogen gas is }}\) \(4.7 \times 10^{-5}\), explain why liquid nonane does not forthwith decompose into its elements.

The entropy change \(\Delta S^{0}\) for the formation of chloroethane by chlorination of ethane is \(+0.5 \mathrm{e} . \mathrm{u}\), and for the formation of chloroethane by combination of hydrogen chloride with ethene \(\Delta S^{0}\) is \(-31\) e.u. Explain. $$ \begin{array}{ll} \mathrm{CH}_{3}-\mathrm{CH}_{3}+\mathrm{Cl}_{2} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{HCl} & \Delta S^{0}=+0.5 \mathrm{e.u} \\\ \mathrm{CH}_{2}=\mathrm{CH}_{2}+\mathrm{HCl} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl} & \Delta S^{0}=-31 \mathrm{e.u} \end{array} $$

tert-Butyl hypobromite is a radical brominating agent that is similar to tert- butyl hypochlorite (Exercise 4 \(18^{*}\) ), but is less easily prepared than the hypochlorite. A good substitute, provided radical bromination is possible, is a mixture of \(\mathrm{BrCCl}_{3}\) and \(\mathrm{ce}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COCl}\) Thus, bromination of cyclohexene results if a high ratio of bromotrichloromethane to hypochlorite is used. O=C(O)CCC1CCCCC1Br Suggest how this reaction is initiated and propagated, and explain why it is necessary to have an excess of bromotrichloromethane.

Write detailed structures and predict which compound in each pair would have (1) the lower boiling point and (2) the higher water solubility. a. \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}, \mathrm{H}_{3} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) b. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) ?. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{COH}\) d. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}, \mathrm{HCO}_{2} \mathrm{CH}_{3}\) e. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CO}_{2} \mathrm{H}, \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CO}_{2} \mathrm{H}\)

a. N-Bromosuccinimide (NBS) is an excellent brominating reagent and is used widely to prepare bromoalkenes from alkenes (Wohl-Ziegler reaction): The reaction is initiated with chemical initiators (peroxides) and is as selective as bromination with molecular bromine. Write plausible propagation steps (three of them) for this reaction, given the fact that the actual brominating agent appears to be molecular bromine that is generated from NBS by HBr. b. What products would you expect to be formed on bromination of 2 -methylbutane with N-bromosuccinimide?

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