Question

Draw the product formed when A is treated with each series of reagents.

a. [1]$H_{2}O$ ; [2] NaH; [3] $C{H}_{3}Br$

b. [1] CuCN; [2] DIBAL-H; [3] $H_{2}O$

c. [1] $C_6{H}_{5}N{H}_2$; [2] $C{H}_{3}COCl$

Short answer

a

b

c

Step-by-step solution

Aryl diazonium salts 

Aryl diazonium salts get subjected to two reactions which are substitution reaction and coupling reaction. Several substituted benzenes are formed by the replacement of nitrogen atoms by another atom or group. An azo compound is formed when the diazonium salt is coupled with a benzene derivative.

Substitution reactions of Aryl diazonium salts 

The combination of the diazonium salt with water leads to the formation of phenol. Benzonitriles can be created by the combination of the diazonium salt with copper cyanide.

Product formed when compound A is treated with a series of reagents

a. In this reaction 3-chlorobenzenediazonium chloride reacts with water to form 3-chlorophenol. This compound reacts with NaH to form 3-chlorophenoxide, which then reacts with to form 1-chloro-3-methoxybenzene. The reaction is given as:

Reaction of compound a with $H_{2}O$, NaH, and $C{H}_{3}Br$

b. In this reaction, 3-chlorobenzene diazonium chloride reacts with CuCN to form 3-chlorobenzonitrile. This can react with DIBAL-H and water to form 3-chlorobenzaldehyde. Hence, the final product of this reaction is 3-chlorobenzaldehyde. The reaction is given as:

Reaction of compound a with CuCN, DIBAL-H and $H_{2}O$

c. In this reaction, 3-chlorobenzene diazonium chloride reacts with aniline to form 4-((3-chlorophenyl)diazenyl)aniline, which reacts with acetyl chloride to form N-4-((3-chlorophenyl)diazenyl) phenyl) acetamide. The product formed when A is treated with the given series of reagents is N-4-((3-chlorophenyl)diazenyl) phenyl) acetamide. The reaction is given as:

Reaction of compound a with $C_6{H}_{5}N{H}_2$ and$C{H}_{3}COCl$