Question
Question: The reactivity of halide ion in alkyl halide is: A. F > Cl > Br >I B. F < Cl < Br C. I > CI > Br...
The reactivity of halide ion in alkyl halide is:
A. F > Cl > Br >I
B. F < Cl < Br C. I > CI > Br >F
D. Br >I > Cl>F
Solution
Substitution nucleophilic bimolecular SN2 reaction-
Nucleophilic substitution bimolecular or SN2 is a single step bimolecular reaction in which the incoming nucleophile attacks the C-atom of substrate in a direction opposite to the outgoing nucleophile.
The reaction passes through a transition state in which both the incoming and outgoing nucleophiles are bonded to the same C-atom.
Complete step by step answer:
In the transition state, the C-atom is sp2 hybridised with a p-orbital whose one lobe overlaps with an orbital of incoming nucleophile and the other lobe overlaps with an orbital of outgoing nucleophile. The three non-reacting atoms or groups attached to the C-atom are nearly coplanar at an angle of 1200. The reaction is completed when the outgoing nucleophile leaves with the bond pair of electrons and simultaneously the incoming nucleophile binds to the C-atom. As the reaction progresses, the configuration of the C-atom under attack is inverted. An SN2 reaction is always accompanied by inversion of configuration. The inversion in configuration implies change in configuration from R to S or S to R (provided the incoming nucleophile and outgoing nucleophile have same priority) and not from (+) to (-) or (-) to (+).
Steric hindrance plays a very vital role in an SN2 reaction. As steric hindrance increases the rate of SN2 reaction decreases. Thus for the same halogen the reactivity order of alkyl halides towards the reaction is as under
Methyl halide > 10-Alkyl halide > 20-Alkyl halide > 30-Alkyl halide
For the same alkyl group, the reactivity of alkyl halides increases with the decrease in C-X bond dissociation energy. Therefore, R-I>R-Cl > R-Br> R-F.
So the correct option is C.
Note:
Group 17 elements are called halogens and they consist of seven valence electrons in their valence shell. SN2 results in inversion of configuration, whereas, in SN1, retention of the structure occurs.