Engineering
Chemistry
Inductive Effect
Nucleophilic Substitution
Basic Concepts of GOC
Question

Which of the following statements is / are true :

Increase in the no. of phenyl ring at C of C–X causes a shift in mechanism from SN2 to SN1.

Greater solvation of attacking nucleophile & poor solvation of transition state promotes the reaction by SN2 mechanism.

Major part of energy needed for the heterolysis of C–X bond in SN1 reaction mechanism is obtained by the solvation of X– by the polar protic solvent.

Allyl & benzyl halides undergo SN2 reactions as they are primary halides which do not give SN1 reaction.

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Solution
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Let's evaluate each statement:

Statement 1: True. The heterolysis of the C–X bond is highly endothermic. The energy required is largely provided by the solvation energy released when the polar protic solvent stabilizes the X⁻ ion.

Statement 2: False. Allyl and benzyl halides are primary but undergo SN1 reactions readily due to resonance stabilization of the carbocation intermediate.

Statement 3: True. Adding phenyl groups increases steric hindrance and stabilizes the carbocation via resonance, favoring SN1 over SN2.

Statement 4: False. Greater solvation of the nucleophile makes it less reactive. Poor solvation of the transition state would destabilize it, hindering the SN2 reaction, not promoting it.

Final Answer: Statements 1 and 3 are true.