Question

There are two main types of covalent bond breakage. In homolytic breakage (as in Table 9.2, p. 371), each atom in the bond gets one of the shared electrons. In some cases, the electronegativity of adjacent atoms affects the bond energy. In heterolytic breakage, one atom gets both electrons and the other gets none; thus, a cation and an anion form.
(a) Why is the C¬C bond in H₃C¬CF₃ (423 kJ/mol) stronger than that in H₃C¬CH₃ (376 kJ/mol)?

Answer 1

The C¬C bond in H₃C¬CF₃ (423 kJ/mol) stronger than that in H₃C¬CH₃ (376 kJ/mol) because of the strong negative inductive effect of fluorine atom

What is Inductive effect?

When an electron- withdrawing or an electron- releasing species is allow to introduce to a chain of atoms (generally a carbon chain), according to the species corresponding negative or positive charge is start relayed through the carbon chain by the atoms through which it attached. This makes a permanent dipole to arise in the molecule and is referred to as the inductive effect.

Types of Inductive effect

+ inductive effect

- inductive effect

What is negative inductive effect?

Whenever an electronegative atom, like halogen, is introduced to a chain of carbon atoms (generally carbon atoms), this results in unequal sharing of electrons which generates a positive charge which is transmitted through the chain.

This make a permanent dipole to arise in the molecule whereas the electronegative atom get a negative charge and the effect is known as the electron-withdrawing inductive effect, or the -I effect.

Thus, we concluded that the C¬C bond in H₃C¬CF₃ (423 kJ/mol) stronger than that in H₃C¬CH₃ (376 kJ/mol) because of the strong negative inductive effect of fluorine atom.

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