Help! Organic chemistry?

Question

What is the most likely mechanism for the following reaction? (Write the symbol for the reaction mechanism.)
http://i5.tinypic.com/4teyukn.jpg

Answer 1

Since the I is on a tertiary carbon, it is unlikely to be SN2, which occurs when the nucleophile attacks and causes the leaving group to leave, all at the same time. The C is too crowded for that to happen.

The most likely is that the I leaves first, and the ethanol attacks the resulting carbocation. That is an SN1 reaction.

Answer 2

First look at what is going on. You have a halogen that will result in a fairly strong polar influence on the carbon to which it is bound, making the I more negative and the C more positive. The more positive C will be attractive to something electron rich.

The O in the alcohol has 2 lone pairs of electrons seeking something with a positive polarity. The O is a nucleophile - and will attack the polarized C.

Clearly this is a saturated carbon so this is nucleophilic substitution at saturated carbon. This means it is a S sub N style of mechanism - for substitution nucleophilic; We now need to ask ourselves if it is first or second order to determine if it is S sub N 1 or S sub N 2.

Look at the reaction - it consumes ethanol and the solvent is ethanol. Do you think it would go faster if you doubled the ethanol? What if you doubled the other reactant? If you believe it will increase with BOTH doubled it is S sub N 2; if you feel it will increase rate with only the I containing reactant doubled, then it is S sub N 1. I am not going to give you the answer here - you need to think it through.

Answer 3

SN2 REACTION!