Question

In the following sequence of reactions. The compound $\left[ C \right]$ formed will be:
C{{H}_{3}}-CH\left( N{{H}_{2}} \right)-C{{H}_{3}}\xrightarrow{\text{ }HN{{O}_{2}}}\left[ A \right]\xrightarrow{\text{ }Oxidation\text{ }}\left[ B \right]\xrightarrow[{{H}^{+}}/{{H}_{2}}O\text{ }]{\text{ }C{{H}_{3}}MgBr\text{ }}\left[ C \right].

Answer 1

Hint : We know that the Primary and secondary amines react with alkyl halides to form tertiary amines. The primary or secondary amine acts as a nucleophile and performs nucleophilic substitution at an alkyl halide. On removal of HX, secondary or a tertiary amine is regenerated respectively. The secondary amine is a more powerful nucleophile and again reacts similarly with another alkyl halide forming tertiary amine.

Complete Step By Step Answer:
Amines are the types of organic compounds that are either mainly based on nitrogen or contain nitrogen. Generally, the structure of amines is similar to that of ammonia with three hydrogen atoms bonded to the nitrogen atom. However, they have different and extra properties due to the difference in carbon bonding or chains. Organic Alkane chain(alkyl) and aromatic ring (aryl groups) substitute one or more hydrogen atoms in the ammonia to form amines. There is one more compound similar to amine that contains three bond ammonia in the ground state called amides.
Amines can be classified into three categories, namely primary, secondary, and tertiary amines. It entirely depends upon the number of carbon atoms in the containing group in the amine chain structure. If there is only one group containing a carbon atom attached to the amine chain, then it is a primary amine molecule. Whereas if there are two groups containing carbon atoms attached to the amine structure, then it is a secondary amine. Isopropyl amine reacts with nitrous acid to form isopropyl alcohol. On oxidation acetone is obtained which then reacts with methyl magnesium iodide (a Grignard reagent) followed by acid hydrolysis to give $1,\text{ }1-dimethylethanol.$
$ \underset{Isopropyl\text{ }Amine}{\mathop{C{{H}{3}}-CH\left( N{{H}{2}} \right)-C{{H}{3}}}},\xrightarrow{\text{ }HN{{O}{2}}\text{ }}\underset{\begin{smallmatrix}
Isopropyl\text{ }Alcohol \\

\end{smallmatrix}}{\mathop{C{{H}_{3}}-CH\left( OH \right)-C{{H}_{3}}}}\, $   
On further solving we get;  
$ \underset{\begin{smallmatrix}   
Isopropyl\text{ }Alcohol \\\   
~~~~~~~~~~~~~[\alpha ]   
\end{smallmatrix}}{\mathop{C{{H}_{3}}-CH\left( OH \right)-C{{H}_{3}}}}\,\xrightarrow{\text{ }Oxidation\text{ }}\underset{\begin{smallmatrix}   
Acetone \\\   
~~~[\beta ]   
\end{smallmatrix}}{\mathop{C{{H}_{3}}-C\left( =O \right)-C{{H}_{3}}}}\, $   
Further we get;  
$ \underset{\begin{smallmatrix}   
Acetone \\\   
~~~[\beta ]   
\end{smallmatrix}}{\mathop{C{{H}_{3}}-C\left( =O \right)-C{{H}_{3}}}}\,\xrightarrow[\text{ }{{H}^{+}}/{{H}_{2}}O\text{ }]{C{{H}_{3}}MgBr}\underset{\begin{smallmatrix}   
1,1-dimethylethanol \\\   
~~~~~~~~~~~~~~[C]   
\end{smallmatrix}}{\mathop{C{{H}_{3}}-C\left( 2C{{H}_{3}} \right)-OH}}\, $   
 
**Note :**  
Remember that similarly, if there are three carbon-containing groups, then it is a tertiary amine. According to energy, it is sometimes suitable to use the nitrogen-containing lone pair of electrons as a nucleophile. This lone allows a fourth group containing carbon to attach to the amine molecule. Such cases are referred to as quaternary ions of ammonium. We can also classify compounds based on the number of amine groups they contain in their molecules (called amino groups).