Question

Heterolysis of a carbon - chlorine bond produces?
A. Two free radicals.
B. Two carbocations.
C. One cation and one anion
D. Two carbanions

Answer 1

Hint: The process of breaking a covalent bond in which one species takes away both the bonding electrons after breaking the bond is known as heterolysis. The more electronegative species generally takes away both the electrons.

Complete step by step answer: The electronegativity difference in the carbon – chlorine bond is higher. The chlorine atom is more electronegative than the carbon atom.
The heterolysis of carbon – chlorine bonds two species. One species is positively charged and the other one is negatively charged.
The electronegativity of the chlorine atom is higher and thus, it pulls both the bonding electrons toward itself.
Thus, the chlorine atom becomes negatively charged.
The electronegativity of the carbon atom is less and thus, it cannot pull the electrons towards itself.
Thus, the carbon atom becomes positively charged.
${\text{C}} - {\text{Cl}} \to {{\text{C}}^ + } + {\text{C}}{{\text{l}}^ - }$
A positively charged species is known as a cation and a negatively charged species is known as an anion.
Thus, heterolysis of carbon – chlorine bond produces one carbon cation and one chlorine anion.
Thus, heterolysis of carbon – chlorine bond produces one cation and one anion.
Thus, the correct option is option (C).

Additional Information: Homolysis of any bond results in production of free radicals or atoms along with unpaired valence electrons. During homolysis, the two bonding electrons get divided equally between two products. Hemolysis occurs in non-polar molecules that are hit by UV light. The energy required for the heterolysis of any bond is known as heterolytic bond dissociation energy. The energy required for the homolysis of any bond is known as homolytic bond dissociation energy.

Note: The energy required for the heterolysis of any bond is known as heterolytic bond dissociation energy. The less electronegative species or the more electropositive species cannot pull the electron towards itself. Thus, less electronegative species becomes positively charged and forms a cation.