TLC Analysis of a Synthesis Reaction

[irunshow]

This is the link for the assignment: http://imageshack.us/f/840/assignmentsynthesisofev.jpg/

Homework Statement

Given in the link

Homework Equations

Why would the proposed synthesis be successful if the reaction stopped after 2 hrs?
How does H attack compound 2 to create compound 3?

The Attempt at a Solution

After 2 hrs. Compound 1 is higher than compound 2. Compound 1 is less polar than compound 2. So if that was the case, than the products would be compound 2.

I don't understand why H would react with the OH group and detach it away from Compound 2.


Thank you for the help!

 

[chemisttree]

You need to answer the following:

1. Why at 1 hour are there two spots and what do they represent. Draw them in ChemDraw.
2. What is likely in the pot at two hours.
3. Why is this initially-formed product at a lower Rf than the starting material.
4. Is it possible that the second product formed was a reaction product of your starting material and why or why not?
5. What is the likely structure of the second product. Use ChemDraw.

 

[irunshow]

^^ Thanks