Chemistry: Not a Friedel-Crafts Reaction

[themonk]

Homework Statement

(a) Draw the product that would be formed.
(b) Provide a brief explanation for this and provide a couple of sentences and key mechanistic step(s) to illustrate your reasoning

The Attempt at a Solution

Here is my reasoning and what I believe the reaction would turn out to be if Benzene was reacted with C₅H₁₁Cl:

Alkyl halides, among other molecules such as alkenes and alcohols would not form according to Friedel-Crafts' reaction because there are more stable molecules or carbocations. C₅H₁₁Cl would change to tert-Butylbenzene (below) because the intermediate of the product would create a 3° structure first from the non-Cl side.

http://commons.wikimedia.org/wiki/File:Tert-Butylbenzene.svg"

Does this seem reasonable? I know that the 3° is the most stable of the carbocations, but I do not know if this is correct reasoning for the reaction. Does the Cl perhaps remain attached also?

 

[themonk]

I re-looked at it, and noticed that there would be a carbon missing if the answer was what I put.

I would change my answer so that the middle Carbon furthest from benzene would have another carbon.

Does this seem more reasonable?

 

[DDTea]

You're on the right track. Friedel-Crafts alkylation involves a carbocation intermediate. As with all carbocations, this intermediate will rearrange itself.

This wouldn't form a t-butyl carbocation, by the way, it would form a neopentyl carbocation. One way that this group can rearrange is through a methyl shift, which would put the positive charge on a tertiary center.