[madscientist]

I am starting organic chemistry this semester and just need someone to confirm what I think is the right way to attack a question i have.

I have to draw an energy profile including the reactant and product, and the transition state or intermediate for the reaction:

1-bromo-3-methylbutane with NaOH(aq)/heat----->

Im finding it hard to decide whether or not its a Sn2 or Sn1 reaction, am i right to say that the reactant is a
3^o carbocation therefore it would be a Sn1 reaction.

and is this the correct structure for 1-bromo-3-methylbutane?

H2C-CH-CH2-CH2-Br
        |
        CH3

Any hint of help would be greatly appreciated.

cheers,

madscientist

[Mitch]

There is no way to form a tertiary carbocation from the reactants you provided. You have a correct structure by the way. Look at the other reactant, it will give a clue that more may be involved then simple SN1 or SN2. You are using a base afterall.

[madscientist]

Thanks mitch for your reply, I only thought it was a n Sn1 on Sn2 because the question states that its a substitution reaction??

what else would it be?

im realy lost with this so ill shove my nose into a book and do some more readin!

cheers,

madscientist

[madscientist]

I know the reaction involved is written out like this:

       CH3                                               CH3
        |                                 HEAT           |
CH3-CH-CH2-CH2-Br + NaOH-------->CH3-CH-CH2-CH2-OH + NaBr

My guts tellin me that it is a Sn2 substitution with one transition state and no reaction intermediate.

please tell me if im right cause i cant see any other way to look at it.

cheers,

madscientist

[Mitch]

sounds fine. Also read about E2 reactions too, before class.