Question

A molecule of formula C₉H₁₀O₃ reacts consecutively as shown below to produce the secondary amine. Identify the structure of the C₉H₁₀O₃ molecule and the material that is produced after the first step.

Answer 1

Concepts and reason

The given problem is based on the identification of the unknown compound with a given molecular formula from the function of the reagent used. Different functional groups have different functions and attack at a specific position or group.

Reductive amination is an organic reaction in which a carbonyl group is converted into an amine. The intermediate formed in the reaction is imine. Imines are the compounds in which the carbon and nitrogen are doubly bonded to each other.

Fundamentals

Sodium cyanoborohydride $\left( {{\rm{NaB}}{{\rm{H}}_{\rm{3}}}{\rm{CN}}} \right)$ is a reducing agent similar to ${\rm{NaB}}{{\rm{H}}_{\rm{4}}}$ , but it is a mild reducing agent due to the presence of electron withdrawing cyano group. It is commonly employed in reductive amination reactions for the reduction of iminium ion.

The structure of sodium cyanoborohydride $\left( {{\rm{NaB}}{{\rm{H}}_{\rm{3}}}{\rm{CN}}} \right)$ is shown below:

A general reductive amination reaction is as follows:

The second step of the reaction is follows:

Therefore, the product after the first step is shown below:

The first step of the reaction is follows:

Ans:

The structure of ${{\bf{C}}_{\bf{9}}}{{\bf{H}}_{{\bf{10}}}}{{\bf{O}}_{\bf{3}}}$ molecule is shown below:

The structure of the molecule produced after the first step is shown below:

Answer 2

HO HO starting

after 1st step