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Question #44404
The Question
Consider the reaction of phenyl neopentyl ether () with excess concentrated at . Identify the major organic products formed.
Options
- A.
Phenol and 2-iodo-2-methylbutane
- B.
Phenol and 1-iodo-2,2-dimethylpropane
- C.
Iodobenzene and 2,2-dimethylpropan-1-ol
- D.
Iodobenzene and 2-iodo-2-methylbutane
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.
Concepts Behind This Question
Ether Cleavage Patterns|Steric Hindrance in SN2|Pinacol-Pinacolone Rearrangement
Why This Question Is Tricky
Common Mistakes
This question tests a critical exception to the standard ether cleavage rules.
Students are taught the heuristic: 'Ether cleavage with HI proceeds via SN2 for primary/secondary alkyl groups and SN1 for tertiary.' Applying this blindly leads to the assumption of an SN2 attack on the primary neopentyl carbon, yielding 1-iodo-2,2-dimethylpropane (Option B).
The 'Hidden Variable' is the extreme steric hindrance of the neopentyl group, which makes SN2 kinetically unviable despite being a primary center.
This forces the mechanism into an SN1 regime accompanied by a 1,2-alkyl shift, testing the student's ability to prioritize steric and electronic factors over simplified mnemonic rules.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Alcohols, Phenols, and Ethers - Class 12 |
| Concept | Ether Cleavage Patterns |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |