Chemical Compound Transformations with Nitrile Intermediates

How can various transformations be achieved using nitrile intermediates?

a. How can 1-hexanol be converted into 1-heptanamine?

b. What is the process to convert cyclohexanecarboxamide into cyclohexyl ethyl ketone?

c. How can 1-octanol be transformed into 2-decanone?

Answer:

Each of the following transformations involving nitrile intermediates can be achieved using specific chemical reactions:

A nitrile intermediate refers to a chemical compound that is formed as an intermediate product during a reaction involving the conversion of an organic compound into a nitrile functional group.

1-hexanol can be converted into 1-heptanamine through a two-step process:

1. React 1-hexanol with concentrated sulfuric acid (H2SO4) to form 1-hexene.

2. Treat 1-hexene with sodium cyanide (NaCN) in the presence of a polar solvent like dimethyl sulfoxide (DMSO) to form 1-hexanenitrile. This intermediate can then be hydrolyzed to produce 1-heptanamine using dilute acid and water.

To convert cyclohexanecarboxamide into cyclohexyl ethyl ketone:

1. React cyclohexanecarboxamide with phosphorous pentoxide (P2O5) or thionyl chloride (SOCl2) to produce cyclohexanecarbonitrile (cyclohexyl cyanide).

2. Hydrolyze cyclohexanecarbonitrile using a strong base like sodium hydroxide (NaOH) to form cyclohexyl carboxylic acid. Then, react the acid with an alcohol such as ethanol (CH3CH2OH) in the presence of an acid catalyst, like sulfuric acid (H2SO4), to complete the transformation into cyclohexyl ethyl ketone.

Convert 1-octanol into 2-decanone by:

1. React 1-octanol with concentrated sulfuric acid (H2SO4) to obtain 1-octene.

2. Treat 1-octene with sodium cyanide (NaCN) using a polar solvent like dimethyl sulfoxide (DMSO) to produce 1-octanenitrile. Finally, hydrolyze the nitrile with a dilute acid and water to yield 2-decanone.

By understanding these specific steps, it is possible to achieve these chemical compound transformations using nitrile intermediates.