Question

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. $C{H}_{3}CHO,NaB{H}_{3}CN$

Short answer

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

Step-by-step solution

Reductive amination

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

Product formation

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