COMEDK2023Morning ShiftChemistryHaloalkanes and HaloarenesActual
t -butyl chloride preferably undergo hydrolysis by
Options
- Aany of (a) and (b)
- BS _ N 1 mechanism
- CNone of the above
- DS _ N 2 mechanism
Correct answer
B. S _ N 1 mechanism
Step-by-step solution
t -butyl chloride is a tertiary alkyl halide, represented as (CH₃)₃CCl . In nucleophilic substitution reactions, tertiary alkyl halides are highly sterically hindered, which prevents the approach of a nucleophile from the backside, making the S _ N 2 mechanism extremely slow or unfavorable. Conversely, the carbocation formed after the departure of the chloride ion, (CH₃)₃C⁺ , is a tertiary carbocation, which is highly stabilized by the inductive effect and hyperconjugation of the nine surrounding hydrogen atoms. Du