Chemistry Alcohols & Phenols NUMS 2024
PMDC Verified Question 21 of 95
The increasing order of reactivity of alcohols towards nucleophile is:
A
2-methyl-2-pentanol < 3-methyl-2-pentanol < 2-methyl-1-pentanol
B
2-methyl-2-pentanol > 3-methyl-2-pentanol > 2-methyl-1-pentanol
C
2-methyl-1-pentanol < 3-methyl-2-pentanol < 2-methyl-2-pentanol
D
2-methyl-1-pentanol > 3-methyl-2-pentanol < 2-methyl-2-pentanol
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: 2-methyl-1-pentanol < 3-methyl-2-pentanol < 2-methyl-2-pentanol
Concept:

When alcohols react with nucleophiles (e.g., halide ions in the Lucas test), the reaction proceeds via the cleavage of the C-O bond (an \(\text{S}_N1\) mechanism for 2°/3°). The reactivity is governed entirely by the stability of the carbocation intermediate.

Formula:

$$ \text{Carbocation Stability: } 3^{\circ} > 2^{\circ} > 1^{\circ} $$

Solution:

  • First, classify each alcohol:


  • 2-methyl-1-pentanol has the -OH on C1. It is a Primary (1°) alcohol.


  • 3-methyl-2-pentanol has the -OH on C2 (bonded to C1 and C3). It is a Secondary (2°) alcohol.


  • 2-methyl-2-pentanol has both a methyl group and an -OH on C2. It is a Tertiary (3°) alcohol.


  • Increasing order means lowest to highest. Therefore: Primary < Secondary < Tertiary.


  • This matches the sequence: 2-methyl-1-pentanol < 3-methyl-2-pentanol < 2-methyl-2-pentanol.


Why other options are incorrect:

Option A is the decreasing order. Options B and D use incorrect mathematical signs or scrambled logic for the established carbocation stability trend.

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