Question

Methyl isocyanide on hydrolysis gives:
A. \[{\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{N}}{{\rm{H}}_{\rm{2}}}\]
B. HCOOH
C. \[{\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{COOH}}\]
D. Both (a) and (b)

Answer 1

Hint: Methyl isocyanide is a chemical species where the methyl group is connected to the N atom. The chemical formula of methyl isocyanide is\[{\rm{C}}{{\rm{H}}_{\rm{3}}} - {\rm{NC}}\] . The net charge of the methyl isocyanide is -1. Isocyanide is one of the functional groups of the formula \[{\rm{N}} \equiv {\rm{C}}\] .

Complete Step by Step Solution:
Let's understand hydrolysis in detail. A chemical reaction where chemical bonds (one or more) undergoes breaking by a water molecule is termed Hydrolysis. The acidic hydrolysis of cyanide gives carboxylic acid. And the acidic hydrolysis of isocyanides results in the formation of primary amines.

The hydrolysis of methyl isocyanide in acidic medium is as follows:
\[{\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{NC}} + {{\rm{H}}_{\rm{2}}}{\rm{O/}}{{\rm{H}}^ + } \to {\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{N}}{{\rm{H}}_{\rm{2}}} + {\rm{HCOOH}}\]

The products obtained due to hydrolysis reactions are methylamine and formic acid.

Hence, the right answer is option D.

Additional information:
Let's understand the hydrolysis reaction of methyl cyanide. When methyl cyanide undergoes acidic hydrolysis, the product obtained is carboxylic acid. The chemical reaction is,
\[{\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{CN}} + {{\rm{H}}_{\rm{2}}}{\rm{O/}}{{\rm{H}}^ + } \to {\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{COOH}}\]
Let's understand some of the chemical properties of methyl cyanides and methyl isocyanides. The polarity of Methyl cyanide is more than methyl isocyanides. Also, there is a greater attractive force in methyl isocyanides. So, the dipole moment of methyl isocyanides is greater. This results in a higher boiling point of methyl cyanide. The odour of cyanide is almond-like.

Note: It is to be noted that cyanides and isocyanides are two different functional groups. The formula for cyanide is CN and the formula for isocyanide is NC. In cyanides, the C atom forms a bond with other groups. But in isocyanides, the N atom forms bonds with other groups.