41aE - Organic Chemistry (Mcmurry)

Question

Which compound in each of the following pairs will react faster in an $S_{N}2$reaction with $O{H}^{-}$?

$C{H}_{3}BrorC{H}_{3}I$

Step-by-Step Solution

Answer

a.$C{H}_{3}I$

S N 2 reaction

It is a nucleophilic substitution reaction in which old bond is breaks break and new bond is formed both the process occur simultaneously. Hence, it’s a single step reaction.

The two reacting species are involved in the rate determining steps.

Nucleophile

Nucleophiles Nucleophile are negatively charged ions or the neutral species having the lone pair of electrons which are ready for bonding.

Species react faster with O H -

If the species is a better leaving group then it react faster with the nucleophile 

I is a better leaving group than Br due to its large size the bond of C-I is weak than C-Br bond so C-I bond get easily break and nucleophilic substitution takes place.

${\text{\hspace{0.33em}CH}}_{\text{3}}{\text{I \hspace{0.33em}shows\hspace{0.33em}fast\hspace{0.33em}reaction\hspace{0.33em}than CH}}_{\text{3}}\text{Br}$