Question 15 Marks
A hydrocarbon 'A', $\left(\mathrm{C}_4 \mathrm{H}_8\right)$ on reaction with HCl gives a compound ' B ', $\left(\mathrm{C}_4 \mathrm{H}_9 \mathrm{Cl}\right)$, which on reaction with 1 mol of $\mathrm{NH}_3$ gives compound ' C ', ( $\left.\mathrm{C}_4 \mathrm{H}_{11} \mathrm{~N}\right)$. On reacting with $\mathrm{NaNO}_2$ and HCl followed by treatment with water, compound ' C ' yields an optically active alcohol,'D'. Ozonolysis of 'A' gives 2 mols of acetaldehyde. Identify compounds 'A' to 'D'. Explain the reactions involved.
Answer
View full question & answer→Addition of HCl has occurred on 'A'. This implies 'A' is an alkene.$\text{A}\xrightarrow{\text{Ozonolysis}}2\text{CH}_3\text{CHO}$
$\text{C}_4\text{H}_8\xrightarrow{\text{HCl}}\text{C}_4\text{H}_9\text{Cl}\\\ \ \text{(A)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}$
Cl in compound ‘B’ is substituted by $NH_2$ to give ‘C’.$\text{C}_4\text{H}_9\text{Cl}\xrightarrow{\text{NH}_3}\text{C}_4\text{H}_{11}\text{N}\\\ \ \text{(B)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}$
‘C’ gives a diazonium salt with $NaNO_2 /HCl$ that liberates $N_2$ to give optically active alcohol. This means that ‘C’ is an aliphatic amine. Number of carbon atoms in amine is same as in compound ‘A’.$\text{(C)}\xrightarrow[\text{H}_2\text{O}]{\text{NaNO}_2/\text{HCl}}\text{(D)}$
Since products of ozonolysis of compound ‘A’ are $CH_3-CH-O$ and $O-CH-CH_3$. The compound ‘A’ is $CH_3-CH-CH-CH_3$. On the basis of structure of ‘A’ reactions can be explained as follows:$\text{CH}_3\text{A}-\text{CH}=\text{CH}-\text{CH}_3\xrightarrow{\ \ \text{HCl}\ \ }\text{CH}_3\text{CH}_2-\text{CH}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(A)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}$
$\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\xrightarrow{\text{NH}_3}\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{NH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}$
$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_2\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\xrightarrow[\text{H}_2\text{O}]{\text{NaNO}_2/\text{HCl}}\text{CH}_3-\text{C}-\text{H}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{NH}_2\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(Optically active)}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(D)}$
$\text{C}_4\text{H}_8\xrightarrow{\text{HCl}}\text{C}_4\text{H}_9\text{Cl}\\\ \ \text{(A)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}$
Cl in compound ‘B’ is substituted by $NH_2$ to give ‘C’.$\text{C}_4\text{H}_9\text{Cl}\xrightarrow{\text{NH}_3}\text{C}_4\text{H}_{11}\text{N}\\\ \ \text{(B)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}$
‘C’ gives a diazonium salt with $NaNO_2 /HCl$ that liberates $N_2$ to give optically active alcohol. This means that ‘C’ is an aliphatic amine. Number of carbon atoms in amine is same as in compound ‘A’.$\text{(C)}\xrightarrow[\text{H}_2\text{O}]{\text{NaNO}_2/\text{HCl}}\text{(D)}$
Since products of ozonolysis of compound ‘A’ are $CH_3-CH-O$ and $O-CH-CH_3$. The compound ‘A’ is $CH_3-CH-CH-CH_3$. On the basis of structure of ‘A’ reactions can be explained as follows:$\text{CH}_3\text{A}-\text{CH}=\text{CH}-\text{CH}_3\xrightarrow{\ \ \text{HCl}\ \ }\text{CH}_3\text{CH}_2-\text{CH}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(A)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}$
$\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\xrightarrow{\text{NH}_3}\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{NH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(B)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}$
$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_2\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}_2-\text{CH}-\text{CH}_3\xrightarrow[\text{H}_2\text{O}]{\text{NaNO}_2/\text{HCl}}\text{CH}_3-\text{C}-\text{H}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{NH}_2\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(Optically active)}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(C)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{(D)}$






