Question icon
12 grade chemistry others

How would you achieve the following conversions?i) Aniline to Benzonitrileii) Nitrobenzene to phenoliii) Ethyl amine to ethyl isonitrile

Profile image of Aniket Singh
1 Year agoGrade
Answers icon

1 Answer

Profile image of Askiitians Tutor Team
1 Year ago

To achieve the following conversions, specific chemical reactions can be employed. Here's how you can carry out each conversion:

i) Aniline to Benzonitrile:
The conversion of aniline to benzonitrile involves the replacement of the amino group (-NH2) with a cyano group (-CN). This can be accomplished through the Sandmeyer reaction. Here are the steps:

Convert aniline to diazonium salt:
Treat aniline (C6H5NH2) with sodium nitrite (NaNO2) in the presence of hydrochloric acid (HCl) at low temperatures (0-5°C). This reaction forms the diazonium salt.
C6H5NH2 + NaNO2 + HCl -> C6H5N2Cl + NaCl + 2H2O

Convert diazonium salt to benzonitrile:
Next, treat the diazonium salt with cuprous cyanide (CuCN) or potassium cyanide (KCN) in a slightly alkaline medium (aqueous solution of sodium acetate, NaOAc). This reaction replaces the diazonium group (-N2Cl) with a cyano group (-CN), resulting in the formation of benzonitrile.
C6H5N2Cl + KCN -> C6H5CN + N2 + KCl

ii) Nitrobenzene to Phenol:
The conversion of nitrobenzene to phenol involves reducing the nitro group (-NO2) to a hydroxyl group (-OH). This can be achieved through a catalytic hydrogenation reaction. Here are the steps:

Prepare a hydrogenation setup:
Set up a high-pressure hydrogenation apparatus, typically using a catalyst such as palladium on carbon (Pd/C).

Perform the hydrogenation reaction:
Add nitrobenzene (C6H5NO2) to the reaction vessel and introduce hydrogen gas (H2) at high pressure in the presence of the catalyst. The reaction is carried out at elevated temperatures and pressures.
C6H5NO2 + 3H2 -> C6H5OH + 2H2O

Collect and purify the product:
Collect the reaction mixture and purify the resulting phenol (C6H5OH) using appropriate methods such as distillation or extraction.

iii) Ethylamine to Ethyl isonitrile:
The conversion of ethylamine to ethyl isonitrile involves the transformation of an amine (-NH2) to an isonitrile (-NC). This can be achieved through the Carbylamine reaction. Here are the steps:

Prepare a reaction mixture:
Mix ethylamine (C2H5NH2) with chloroform (CHCl3) and ethanol (C2H5OH) in the presence of a strong base like sodium hydroxide (NaOH) or potassium hydroxide (KOH).

Carry out the Carbylamine reaction:
Heat the reaction mixture under reflux conditions. The primary amine reacts with chloroform to form an isocyanide (isonitrile) as a byproduct.
C2H5NH2 + CHCl3 + 3KOH -> C2H5NC + 3KCl + 3H2O

Separate and purify the product:
Separate the ethyl isonitrile (C2H5NC) from the reaction mixture by appropriate techniques like distillation or extraction.

Note: It is important to exercise caution and follow proper laboratory safety protocols when working with chemical reactions.