Question

convert: methanol into tertiary butyl alcohol
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Answer 1

Answer:

Here is your answer

Answer 2

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I ended up choosing one of the surrounding tert-butyl carbons and building the molecule based on that.

Using PBr3 dissolved in pyridine turns an alcohol into an alkyl bromide.

Taking acetylene ( HC≡CH) from a separate process, reacting it with sodium amide ( NaNH2 ) deprotonates one of the protons on acetylene, turning it into a nucleophile. This can backside-attack

CH3Br to generate propyne.

If you use HBr on a terminal alkyne or alkene (a hydrobromination), it will react in a Markovnikov fashion, which means the Br will add onto the more-substituted carbon---the one with less H atoms. So, both Br will go onto the middle carbon.

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