
How does bond dissociation affect carbon compounds?
Answer
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Hint: We know that bond dissociation energy is a measure of strength of bonds between two atoms and the energy is required to break one mole of a bond of a particular type between the atoms in gaseous state under standard conditions.
Complete step by step solution:
Dissociation is what happens when compounds dissolve into individual ions in solution.
Carbon containing compounds do not dissociate in water completely and are generally weak conductors of electricity so we know they will be weak acids/bases.
More the bond dissociation energy, the stronger the bond is. This is used in case of heterolytic cleavage. If the bond cleavage leads to the formation of stable products, it will require less bond dissociation energy. This is used in hemolytic cleavage. The dissociation of the $ C-H $ bond would result in the formation of a radical. By comparing the radical stability, we will be able to compare the bond dissociation energy.
We know that the primary free radical is least stable and the tertiary free radical is the most stable because the tertiary free radical is most stable due to the effect alkyl groups and due to hyperconjugation. Since tertiary radical is most stable and hence the bond between tertiary carbon and hydrogen can be broken easily into tertiary radical and hence will require least bond dissociation energy
Let's look at acetic acid $ \left( C{{H}_{3}}COOH \right) $ a weak acid as an example. When acetic acid dissolves in water, the products are $ C{{H}_{3}}CO{{O}^{1-}}~ $ and $ {{H}_{3}}{{O}^{1+}} $ . However these ions tend to react again to form the original reagents, $ C{{H}_{3}}COOH~ $ and $ {{H}_{2}}O $ When weak acids/bases react w/water, the ions that form have a strong tendency to react w/ each other giving us a chemical equilibrium.
Note:
Remember that Bond can be broken symmetrically or asymmetrically. The former is called hemolytic cleavage and is the basis of the usual bond dissociation energies. Asymmetric dissociation of a bond is called heterolytic cleavage but in gaseous phase, the enthalpy of heterolytic cleavage is larger than hemolytic cleavage, due to the need to separate unlike charges.
Complete step by step solution:
Dissociation is what happens when compounds dissolve into individual ions in solution.
Carbon containing compounds do not dissociate in water completely and are generally weak conductors of electricity so we know they will be weak acids/bases.
More the bond dissociation energy, the stronger the bond is. This is used in case of heterolytic cleavage. If the bond cleavage leads to the formation of stable products, it will require less bond dissociation energy. This is used in hemolytic cleavage. The dissociation of the $ C-H $ bond would result in the formation of a radical. By comparing the radical stability, we will be able to compare the bond dissociation energy.
We know that the primary free radical is least stable and the tertiary free radical is the most stable because the tertiary free radical is most stable due to the effect alkyl groups and due to hyperconjugation. Since tertiary radical is most stable and hence the bond between tertiary carbon and hydrogen can be broken easily into tertiary radical and hence will require least bond dissociation energy
Let's look at acetic acid $ \left( C{{H}_{3}}COOH \right) $ a weak acid as an example. When acetic acid dissolves in water, the products are $ C{{H}_{3}}CO{{O}^{1-}}~ $ and $ {{H}_{3}}{{O}^{1+}} $ . However these ions tend to react again to form the original reagents, $ C{{H}_{3}}COOH~ $ and $ {{H}_{2}}O $ When weak acids/bases react w/water, the ions that form have a strong tendency to react w/ each other giving us a chemical equilibrium.
Note:
Remember that Bond can be broken symmetrically or asymmetrically. The former is called hemolytic cleavage and is the basis of the usual bond dissociation energies. Asymmetric dissociation of a bond is called heterolytic cleavage but in gaseous phase, the enthalpy of heterolytic cleavage is larger than hemolytic cleavage, due to the need to separate unlike charges.
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