Chemistry · Common types of organic reactions: Substitution, addition, elimination and rearrangement
What is the best term to describe the rearrangement that causes the conversion o
What is the best term to describe the rearrangement that causes the conversion of 3 -bromo- 2,2 dimethylbutane to 2,3 -dimethyl-2butanol?
- A. 1,2 -methyl shift
- B. 1, 3- hydride shift
- C. 1,3 -methyl shift
- D. 1,2 - hydride shift
Step-by-step solution
The starting carbocation after bromide loss is secondary and adjacent to a quaternary carbon (C2). A 1,2-methyl shift from C2 to the carbocation at C3 forms a more stable tertiary carbocation at C2. Water then attacks this tertiary carbocation, yielding 2,3-dimethyl-2-butanol.
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