(1) Assuming the equal reactivity of each proton in carbocation formed as an intermediate in dehydration of 2-methyl-2-butanol calculate what should be the ratio of 2-methyl-2-butene to 2-methyl-1-butene. Then, calculate an actual ratio of both products in your experiment (based on GC results).Explain the difference between the calculated and observed results (please, do not provide a trivial answer such as "because protons at x position are more reactive").

(2) Explain, why you used sulfuric acid in the experiment, not HCl.

(3) Give the structures and names (including description of stereochemistry) of three alkenes produced in dehydration of 3-methyl-3-pentanol.

4. What is a purpose of adding sodium carbonate to the flask in the brewing step?

5. Why it is important that your brewed tea be cool before starting liquid-liquid extraction with methylene chloride?

6. (a) Write down the equation for reaction of caffeine with salicylic acid to form caffeine salicylate.

(b) Suppose you got 70 mg of caffeine and you used all of it to synthesize caffeine salicylate. What is the theoretical yield (in grams) of this reaction. Show your calculation.