JEE Main 2020 · 3 September · morning · Single correct · +4 / −1
The mechanism of S N 1 reaction is given as : R-X → R⊕ X⊖ → R⊕ ∥ X⊖ →(Y⊖) R-Y + X⊖
A student writes general characteristics based on the given mechanism as :
(a) The reaction is favoured by weak nucleophiles.
(b) R⁺ would be easily formed if the substituents are bulky.
(c) The reaction is accompanied by racemization.
(d) The reaction is favoured by non-polar solvents.
- (a) (a) and (b)
- (b) (a), (b) and (c)
- (c) (a) and (c)
- (d) (b) and (d)
Answer and solution
Answer (b) (a), (b) and (c)
Solution
Chemistry ma’am · 2 steps
Read the mechanism: a bare carbocation forms first, so ask what helps it form and what happens to it next.
- Slow step. In S_N1 the slow step is R-X breaking into R⁺ and X⁻. The nucleophile Y⁻ joins only after that, so it plays no part in the rate.
Statement What the mechanism says Verdict (a) Weak nucleophiles favour it Y⁻ is not in the slow step. A weak nucleophile does not slow S_N1, but it does slow the competing S_N2. True (b) Bulky groups help R⁺ form Bulky alkyl groups push electrons into R⁺ and are crowded less once the carbon turns planar (sp²), so ionisation is easier. True (c) Racemization occurs R⁺ is planar, so Y⁻ can attack from either face and both enantiomers form. True (d) Non-polar solvents favour it The ion pair and the solvent-separated ion pair need a polar (protic) solvent to stabilise the ions. False - So. Statements (a), (b) and (c) are correct and (d) is wrong, which is option (b).
The idea to keep. For S_N1, think carbocation: stable R⁺ (bulky, tertiary), polar protic solvent, nucleophile strength irrelevant, and a planar ion that gives racemization.
Answer from the NTA final answer key. Solution by PrepWiser.