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NEET 2026
Exam
NEET
Year
2026
Subject
Chemistry
Chapter
Chapter

NEET 2026 · Chemistry · Chapter

An alcohol, whose structure is shown in the figure, is heated with...

An alcohol, whose structure is shown in the figure, is heated with concentrated hydroiodic acid (HI) to yield a major
An alcohol, whose structure is shown in the figure, is heated with concentrated hydroiodic acid (HI) to yield a major alkyl halide product via a substitution mechanism. What is the IUPAC name of this major product?

Options

  1. A2-Iodo-3,3-dimethylbutane
  2. B2-Iodo-2,3-dimethylbutane
  3. C1-Iodo-3,3-dimethylbutane
  4. D2-Iodo-2-methylpentane

Correct answer

B. 2-Iodo-2,3-dimethylbutane

Step-by-step solution

The given reactant is 3,3-dimethylbutan-2-ol. When heated with concentrated HI, the reaction proceeds via an SN1S_N1 mechanism.

The hydroxyl group is first protonated by HI to form a good leaving group (−OH2+-OH_2^+).

Loss of a water molecule generates a secondary carbocation: CH3−C(CH3)2−CH+−CH3CH_3-C(CH_3)_2-CH^{+}-CH_3.

To achieve greater stability, this secondary carbocation undergoes a 1,2-methyl shift, rearranging into a more stable tertiary carbocation: CH3−C+(CH3)−CH(CH3)−CH3CH_3-C^{+}(CH_3)-CH(CH_3)-CH_3.

The iodide ion (I−I^-) then acts as a nucleophile and attacks the tertiary carbocation, forming the major product: CH3−CI(CH3)−CH(CH3)−CH3CH_3-CI(CH_3)-CH(CH_3)-CH_3.

The IUPAC name of this major product is 2-iodo-2,3-dimethylbutane.

Answer: 2-Iodo-2,3-dimethylbutane
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