Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Determine the correct decreasing order of the relative rate of reaction for the following compounds with aqueous EtOH / AgNO ₃ . (I) (II) (III)
Options
- AIII > II > I
- BI > II > III
- CIII > I > II
- DI > III > II
Correct answer
A. III > II > I
Step-by-step solution
The reaction of halides with aqueous EtOH / AgNO ₃ proceeds via an S _ N 1 mechanism, where the rate-determining step is the formation of a carbocation. The rate of reaction depends on the stability of the carbocation and the leaving group ability. Compound (I) is a vinylic chloride. The cleavage of the C-Cl bond produces a vinylic carbocation, which is highly unstable. Hence, it is the least reactive. Compound (II) is an allylic chloride. It forms a secondary allylic carbocation, which is stabilized by resonance w