Chemistry Alcohols & Phenols NUMS 2023
PMDC Verified Question 36 of 95
The order of reactivity of alcohol when C-O bond breaks is:
A
Tertiary alcohol > secondary alcohol > Primary alcohol
B
Secondary alcohol > Primary alcohol > tertiary alcohol
C
Primary alcohol > Secondary alcohol > tertiary alcohol
D
Tertiary alcohol > primary alcohol > secondary alcohol
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: Tertiary alcohol > secondary alcohol > Primary alcohol
Concept:

Reactions that cleave the carbon-oxygen (C-O) bond in alcohols (such as reaction with hydrogen halides, \(\text{S}_N1\) pathway) involve the formation of a carbocation intermediate.

Formula:

$$ \text{R}_3\text{C-OH} \xrightarrow{\text{H}^+} \text{R}_3\text{C}^+ + \text{H}_2\text{O} $$

Solution:

  • The rate of reaction is directly proportional to the stability of the carbocation formed after water leaves.


  • Alkyl groups donate electron density (hyperconjugation and inductive effect), stabilizing positive charge.


  • A tertiary carbocation (three alkyl groups) is highly stable, whereas a primary carbocation is very unstable.


  • Therefore, the reactivity order for C-O bond cleavage is Tertiary > Secondary > Primary.


Why other options are incorrect:

Option C is the order of reactivity for reactions where the O-H bond breaks (acting as an acid), which is dictated by alkoxide stability, not carbocation stability.

Quality & Fidelity Assurance: Every question on BeambePrep is rigorously curated against the official PMDC syllabus with zero filler, zero out-of-syllabus content, and zero typos. When an authentic past paper originally contained a historical mistake or ambiguity from the examining board (such as UHS or NUMS), BeambePrep faithfully reflects the original paper while detailing the nuance and scientific consensus in the autopsy above.

Want to solve full-length papers under timed exam conditions?

Practice with zero-scroll lockdown sprints, dynamic latency zone timers, live peer selection telemetry, and the automated Amber mistake recovery loop.