(N/A) Definition: When a covalent bond breaks in such a way that both electrons of the covalent bond (i.e.,shared pair) are taken away by one of the bonded atoms,the mode of bond cleavage is called heterolytic fission. After heterolysis,one atom has a sextet electronic structure and a positive charge,while the other has a valence octet with at least one lone pair and a negative charge.
$(a)$ Heterolytic fission producing carbocation: e.g.,Heterolytic cleavage of $CH_3Br$ gives $CH_3^+$ (methyl cation) and $Br^-$ (bromide ion).
$H_3C-Br \xrightarrow{\text{Heterolytic}} H_3C^+ + :Br^-$
$\rightarrow$ Both electrons of the $C-Br$ bond are transferred to $Br$. Thus,$Br$ gains the non-bonding electron pair,an octet,and a negative charge.
$\rightarrow$ $A$ species having a carbon atom with a sextet of electrons and a $+1$ positive charge is called a carbocation. The $CH_3^+$ ion is known as a methyl cation.
$\rightarrow$ The positively charged carbon of $CH_3^+$ possesses $sp^2$ hybridization and has a trigonal planar shape.
$(b)$ Heterolytic fission producing carbanion: The heterolytic cleavage can also produce species in which carbon retains the shared pair of electrons,obtaining a negative charge. e.g.,When a group $Z$ attached to a carbon leaves without the electron pair,a carbanion is formed.
$H_3C-Z \xrightarrow{\text{Heterolytic}} H_3C:^- + Z^+$
In this case,the carbon atom retains the shared pair of electrons,resulting in a carbanion $(H_3C:^-)$.