NEETChemistryAlcohols Phenols and Ethers
Given below are two statements: one is labelled as Assertion (A) and the other is labelled as Reason (R). Assertion (A): Reaction of 2,2-dimethylpropan-1-ol with HBr gives 2-bromo-2-methylbutane as the major product. Reason (R): The reaction involves a 1,2-methyl shift to form a more stable tertiary carbocation. In the light of the above statements, choose the most appropriate answer from the options given below:
Options
- AAssertion (A) is false but Reason (R) is true.
- BAssertion (A) is true but Reason (R) is false.
- CBoth Assertion (A) and Reason (R) are correct but Reason (R) is not the correct explanation for Assertion (A).
- DBoth Assertion (A) and Reason (R) are correct and Reason (R) is the correct explanation for Assertion (A).
Correct answer
D. Both Assertion (A) and Reason (R) are correct and Reason (R) is the correct explanation for Assertion (A).
Step-by-step solution
2,2-dimethylpropan-1-ol (neopentyl alcohol) is a highly sterically hindered primary alcohol. Upon reaction with HBr , the - OH group is protonated to form a good leaving group ( - OH ₂^+ ). Due to the high instability of a primary carbocation, the departure of the water molecule is accompanied by a simultaneous 1,2-methyl shift from the adjacent quaternary carbon. This rearrangement directly yields a more stable tertiary carbocation (tert-pentyl carbocation). The nucleophilic bromide ion ( Br ^- ) then attacks this