Real tricky Organic Chemistry questions

1. Are these molecules optically active?

2. What is the reagent to synthesize this compound using an intramolecular reaction?

3. Propose a mechanism for each of the following reactions.

Cl

CH3

Cl

NH2

NH

OO

OH

CH3

AlCl3

NaOH

S

CH3 OH+ ClH

S OCH3

4. Outline steps on how you can carry out the transformation. You need to use a Grignard

reagent. Please Wikipedia on what is a Grignard reagent.

O OH

CH3

5. Draw another resonance structure of this vinylic alkoxide ion:

OH

CH3

H+

AlCl3

-

6. Why does ethanedioic acid (H2C2O4) have two different pKa values? pK1 = 1.2; pK2 = 4.2

7. Predict the organic product of the following reaction.

O

OH

O

OH

heat

8. Draw 3 resonance structures of phenylamine.

NH2