52 - Organic Chemistry

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.  $C{H}_{3}CHO,NaB{H}_{3}CN$

 

Step-by-Step Solution

Answer

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

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