Orgo: Tert-butylbromide + Water --> ?

[katePharm]

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What is the product of the reaction?

Is it an alkene (dimethylethene) or an alcohol (tert-butanol) ?

 

[Greggy Weggy]

I am pretty sure it turns into an alcohol by nucleophilic substitution.

 

[jason8830]

I am pretty sure it turns into an alcohol by nucleophilic substitution.

Yup...SN1

 

[katePharm]

Yup...SN1

Thats what I thought too but the answer key says 1.2 dimethylethene -.-

 

[jason8830]

Thats what I thought too but the answer key says 1.2 dimethylethene -.-

In order for the E1 product to be the major product, the reaction is usually ran under basic conditions or heated conditions to deprotonate the carbon, so I'm guessing its a typo? Also, 1,2 dimethylethene should be 2-butene which makes me think that this is just a messed up question and I wouldn't get too caught up with it. lol