Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the product(s) for the given S _ N 1 reaction. (i) (ii) (iii) (iv)
Options
- A(ii) and (iii)
- B(iii) and (iv)
- C(i) and (iii)
- D(i) and (ii)
Correct answer
D. (i) and (ii)
Step-by-step solution
The given reaction is specified to proceed via an S _ N 1 mechanism. In an S _ N 1 reaction, the first step involves the departure of the leaving group ( Cl ⁻ ) to form a carbocation intermediate. The resulting cyclopentyl carbocation is sp^2 hybridized, making it planar at the positively charged carbon atom. Because the carbocation is planar, the incoming nucleophile ( CH ₃ CH ₂ S ⁻ ) can attack from either face (top or bottom) with equal probability. Attack from the same face as the original leaving group results