13.5 How will you convert:

(i) Ethanoic acid into methanamine

(ii) Hexanenitrile into 1-aminopentane

(iii) Methanol to ethanoic acid

(iv) Ethanamine into methanamine

(v) Ethanoic acid into propanoic acid

(vi) Methanamine into ethanamine

(vii) Nitromethane into dimethylamine

(viii) Propanoic acid into ethanoic acid?

(i)
The desired transformation is ethanoic acid to methanamine.   

In the first reaction, ethanoic acid reacts with SOCl2 and acetyl chloride is obtained as a product. In the second step, acetyl chloride reacts with ammonia, and an amide is obtained as a product. 


Then amide undergoes a Hoffmann bromamide reaction and then amine is obtained as a product. In this reaction, amide reacts with KOH and Br2

The reactions are as follows:

(ii)

In the first reaction, hydrolysis of hexanenitrile takes place and hexanoic acid is obtained as a product. In the second reaction, the acid reacts with SOCl2 , and the OH group is replaced by a Cl atom.

In the next step, acyl chloride reacts with ammonia, and an amide is obtained as a product. In the last step, amide undergoes a Hoffmann bromamide reaction and is converted into an amine containing 1 carbon less than the starting reactant. 

The reactions are as follows:
 

(iii)
In the first reaction, methanol reacts with PCl5 and is converted into a methylchloride. Then, methylchloride undergoes a substitution reaction(SN2) and an ethanenitrile is obtained as a product. 

In the next step, ethanenitrile undergoes a hydrolysis reaction and ethanoic acid is obtained as a product.
The reactions are as follows:

(iv)

In the first reaction, ethanamine reacts with NaNO2/HCl, and diazonium salt is formed as a product. The diazonium salt obtained from primary aliphatic amine is highly unstable, and it reacts with water and forms alcohol as a product. 

In the next step, alcohol undergoes an oxidation reaction and ethanoic acid is obtained as a product. The ethanoic acid is heated with ammonia and an amide is obtained. Then in the last step, amide undergoes a Hoffmann bromamide reaction with Br2 and NaOH, hence, methanamine is obtained as a product

The reactions are as follows:
 

(v)
In the first reaction, ethanoic acid undergoes a reduction reaction. and ethanol is obtained as a product. In the next step, ethanol reacts with PCl5 , and ethyl chloride is obtained as the product.

In the next step, a substitution reaction occurs and propanenitrile is obtained as a product when ethyl chloride reacts with NaCN. Then in the last step CN group undergoes acid hydrolysis and is converted into an acid group. 

The reactions are as follows:

(vi)

In the first step, methanamine reacts with NaNO2/ HCl and unstable diazonium salt is obtained. Then immediately diazonium salt reacts with water and methanol is obtained as a product.

In the next step, methanol reacts with PCl5 and methyl chloride is obtained as a product. Then methyl chloride reacts with NaCN and ethanenitrile is obtained as a product.

The reduction of ethanenitrile in the next step gives ethanamine as a product. For this reaction, hydrogen and nickel is used as a reagent.

The reactions are as follows:
 

(vii)
In the first step, nitromethane undergoes a reduction reaction in the presence of Sn/HCl, and hence, methanamine is obtained as a product. In the next step, methanamine undergoes a carbylamine reaction, and isocyanide is obtained as a product. 

In this reaction, methanamine reacts with CHCl3 and KOH, and isocyanide is obtained as a product,.

In the last step, the reduction of isocyanide takes place and dimethylamine is obtained as a product. 

The reactions are as follows:

(viii)

In the first reaction, propanoic acid reacts with ammonia, and an amide is obtained as a product. In the next step, amide undergoes a Hoffmann bromamide reaction, and an ethylamine is obtained as a product. 

The ethylamine reacts with NaNO2/HCl followed by water and ethanol is obtained as a product. 

In the last step, oxidation of alcohol takes place using KMnO4 . The reactions are as follows: