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Question

tert-Butyl alcohol, when heated with H2SO4, gives an alkene. Which of the following sequence will convert the alkene to 3-methylbutanoic acid?

1 - H3O+, hydrolysis

2 – treatment with CN

3 – HBr, peroxide


A

3; 2; 1

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B

2; 1; 3

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C

3; 1; 2

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D

1; 2; 3

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Solution

The correct option is A

3; 2; 1


First, we convert the tertiary substrate to 2-methylpropene via dehydration.
The alkene is then converted to a primary alkylbromide via an anti-Markovnikov addition of HBr.
Using a substitution reaction, the CN replaces bromide. The nitrile is hydrolysed to give the acid:


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