Propose which one of the following reactions is more likely to occur through SN1 mechanism?
Correct answer: D. (CH3)3C − Cl CCl4/NaOH → (CH3)3COH
- A. (CH3)2CH − Cl CCl4/NaOH→ CH2)2 CH − OH
- B. C2H5Cl NaOH/H2O→ C2H5 − OH
- C. (CH3)3 CCl H2ONaOH→ (CH3)3C − OH
- D. (CH3)3C − Cl CCl4/NaOH → (CH3)3COH
Explanation
This reaction is more likely to proceed through SN1 mechanism because generally, tertiary alkyl halides are more reactive through this mechanism. They form tertiary carbocation which is most stable hence tertiary alkyl halide is more reactive. The order of reactivity for SN1 reaction is as follows:Tertiary R-X> Secondary R-X> Primary R-XSN1 reaction is also favoured by polar solvent.
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About Nucleophilic Substitution
Nucleophilic substitution replaces a leaving group in an alkyl halide when an electron-rich nucleophile attacks the carbon atom. The topic compares SN1 and SN2 mechanisms, including reaction conditions, substrate structure, solvent effects, nucleophile strength, carbocation formation and stereochemical changes, and distinguishes substitution from elimination.
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