Draw the products formed when p-methylaniline ( $p-C_6{H}_{4}N{H}_2$) is treated with each reagent.

1. HCl
2. $C{H}_{3}COCl$
3. ${\left(C{H}_{3}CO\right)}_{2}O$
4. Excess $C{H}_{3}I$
5. ${\left(C{H}_3\right)}_{2}C=O$
6. $C{H}_{3}COCl,AlC{l}_3$
7. $C{H}_{3}C{O}_{2}H$
8. $NaN{O}_2,HCl$
9. Part (b), then$C{H}_{3}COCl,AlC{l}_3$
10. $C{H}_{3}CHO,NaB{H}_{3}CN$

The conversion of the carbonyl group into the amine group through the intermediate imine is termed reductive amination.

a.

The reaction is shown below.

Formation of the product in a

b.

The reaction is shown below.

Formation of the product in b

c.

The reaction is shown below.

Formation of the product in c

d.

The reaction is shown below.

Formation of the product in d

e.

The reaction is shown below.

Formation of the product in e

f.

The reaction is shown below.

Formation of the product in f

g.

The reaction is shown below.

Formation of the product in g

h.

The reaction is shown below.

Formation of the product in h

i.

The reaction is shown below.

Formation of the product in i

j.

The reaction is shown below.

Formation of the product in j