[University_Of_Toronto]

Give the IUPAC name of the major organic product of the following reaction. Pay attention to stereochemistry if appropriate.

I did the mechanism and I came up with two rxn:

Elimination and Substitution....I somehow have doubts about which is the Major product

Any Help would be appreciated

I attached my entire Mechanism of how I arrived at my answers

[macman104]

Everytime you perform SN2 on a tertiary carbon, your orgo book cries a little .

Sorry, couldn't resist saying that.  Anyway, like above, I would not recommend drawing an SN2 substitution on a tertiary carbon. 

There are a few other routes you could take...

You could make an argument for an SN1 substitution.  If you pull off the same hydrogen from the E2, you can do a methyl shift, and get a secondary carbocation (the bromine carbon).

Also, you have another elimination and substitution route.  Your methyl group dangling off there.  You can eliminate from there and form the hoffman product.  Or, you can do SN1, and have a methyl shift, and get a 7-membered ring.

However, I'd think all of those will still be minor compared to the E2 mechanism you've drawn.  I would think that would be the major product.

EDIT:  Also, thank you very much for posting your attempt!

[agrobert]

You could make an argument for an SN1 substitution.  If you pull off the same hydrogen from the E2, you can do a methyl shift, and get a secondary carbocation (the bromine carbon).

Do you really think you could form a stable carbocation under basic conditions?

[University_Of_Toronto]

So major product is

[agrobert]

The E2 product is major.