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Question

Which of the following sequence of reactions would
convert tertiary butyl alcohol into 3,3-dimethylbutan-1-ol?


A
1: Br2 followed by Mg in Ether; 2: Oxirane 3: H3O+
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B
1: HBr followed by Mg in Ether; 2: Oxirane 3: H3O+
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C
1: HBr followed by Mg in Ether; 2: dioxane 3: H3O+
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D
None of the above
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Solution

The correct option is B 1: HBr followed by Mg in Ether; 2: Oxirane 3: H3O+

The substrate is a tertiary alcohol with exactly 4 carbons whereas the required product is a primary alcohol but with 4 + 2 = 6 carbon atoms - 3,3-dimethylbutan-1-ol.
Somehow, two more carbon atoms need to be added; one of the ways is via a Grignard synthesis using ring opening of oxirane:


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