The reaction of 2,2-dimethyl-1-piopanol with HBr is very slow and gives 2-bromo-

Question

The reaction of 2,2-dimethyl-1-piopanol with HBr is very slow and gives 2-bromo- 2-methyIbutane as the major product. Give a mechanistic explanation for these observations. Select all that apply. Stereoelectronic effects result in an antic op lanar rearrangement of the carbon skeleton. Steric hindrance prevents nucleophilic attack. The mechanism requites the development of an unstable positively charged species in the transition state. The mechanism results in a carbocation rearrangement in which a methyl shift occurs. The mechanism requires dissociation of a poor leaving group.

Explanation / Answer

Option B,C,D,E all are applicable.

B) steric hindrance of tert group prevents the back side attack of Br nucleophile to the substrate. Hence SN2 mechanism does not happen. Though substrate is primary alkylhalide steric hindrance of tert group prevents nucleophillic attack.

C) after elimination OH it leads to formation of primary cation which is less stable than tert carbocation.

D) So methyl shift leads higly stable tert cation by rearrangement.

E) OH is not better leaving group.

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