Q56b - Organic Chemistry (Mcmurry)

Question

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH₃)₃ CCI (CH₃)₃  CBr (CH₃)₃  COH

Step-by-Step Solution

Answer

Answer

b. (CH₃)₃ COH < (CH₃)₃  CCI <  (CH₃)₃   CBr 

Step1: S N 2 reaction

It is the substitution nucleophilic unimolecular reaction. It follows first-order kinetics that it is a two-step reaction in which a carbocation intermediate is formed.

The rate of the reaction depends only on the reacting species is independent of the nucleophile.

Step2: Reactivity towards S N 2 reaction

As the carbocation intermediate is formed in the reaction the reacting species which form the most stable carbocation is more reactive toward the nucleophile.

 Stability of carbocation:

1. 3⁰ > 2⁰ > 1⁰
2. If carbocation showing resonance is more stable than non-resonance carbocation 
3. The best leaving group forms the most stable carbocation as in halogen Br is the best-leaving group then Cl and OH is the poor leaving group.

So, 

       (CH₃)₃ COH < (CH₃)₃  CCI <  (CH₃)₃   CBr 

Reactivity order