Chapter 18: Aromatic Compounds

Question 1

Na2Cr2O7, H2SO4, H2O

With methyl-benzene

Answer 1

Adds: Carboxylic Acid to benzylic position

Question 2

1) KmNO4, H20, heat,
2) H3O+
With methyl-benzene

Answer 2

Adds: Carboxylic Acid to benzylic position

Question 3

NBS, Heat

With methyl-benzene

Answer 3

Adds: Bromine to benzylic position

Question 4

Na, CH3OH, NH3

With benzene

Answer 4

Birch Reduction
Adds: Two H's 
-Na. radicalizes one position which resonantes and forms anionic carbon
-this abstracts hydrogen
-radicalizes again to form anion
-abstracts another hydrogen
-maintians two double bonds
-converts two carbons to sp3
-R group would not be reduced, EWG group carbonwould