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 alkyl halide product via a substitution mechanism. What is the IUPAC name of this major product?
Options
- A2-Iodo-3,3-dimethylbutane
- B2-Iodo-2,3-dimethylbutane
- C1-Iodo-3,3-dimethylbutane
- 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 mechanism.
The hydroxyl group is first protonated by HI to form a good leaving group ().
Loss of a water molecule generates a secondary carbocation: .
To achieve greater stability, this secondary carbocation undergoes a 1,2-methyl shift, rearranging into a more stable tertiary carbocation: .
The iodide ion () then acts as a nucleophile and attacks the tertiary carbocation, forming the major product: .
The IUPAC name of this major product is 2-iodo-2,3-dimethylbutane.
Answer: 2-Iodo-2,3-dimethylbutane
The hydroxyl group is first protonated by HI to form a good leaving group ().
Loss of a water molecule generates a secondary carbocation: .
To achieve greater stability, this secondary carbocation undergoes a 1,2-methyl shift, rearranging into a more stable tertiary carbocation: .
The iodide ion () then acts as a nucleophile and attacks the tertiary carbocation, forming the major product: .
The IUPAC name of this major product is 2-iodo-2,3-dimethylbutane.
Answer: 2-Iodo-2,3-dimethylbutane