Q.52. - Organic Chemistry

Question

Question: Identify compounds A, B, and C.

 

a. Compound A has molecular formula ${\mathit{C}}_{\mathbf{8}}{\mathit{H}}_{\mathbf{12}}$  and reacts with two equivalents of ${\mathit{H}}_{\mathbf{2}}$. A gives $\mathit{H}\mathit{C}\mathit{O}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}\mathit{H}\mathit{O}$ as the only product of oxidative cleavage with ${\mathit{O}}_{\mathbf{3}}$ followed by $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{S}\mathit{C}{\mathit{H}}_{\mathbf{3}}$.

 

b. Compound B has molecular formula ${\mathit{C}}_{\mathbf{6}}{\mathit{H}}_{\mathbf{10}}$ and gives ${\left(C{H}_3\right)}_{\mathbf{2}}\mathit{C}\mathit{H}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}{\mathit{H}}_{\mathbf{3}}$  when treated with excess ${\mathit{H}}_{\mathbf{2}}$  in the presence of Pd. B reacts with $\mathit{N}\mathit{a}\mathit{N}{\mathit{H}}_{\mathbf{2}}$ and $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{I}$ to form compound C (molecular formula  ${\mathit{C}}_{\mathbf{7}}{\mathit{H}}_{\mathbf{12}}$).

Step-by-Step Solution

Answer

Answer

Step 1: Reaction of an alkene with ozone

Treatment of double bond with ozone gives ozonide. Further oxidation gives aldehyde and ketone.

Step 2: Identification of product in a

Structure of A

Step 3: Identification of products in b and c

The formula of compound B is $C_6{H}_{10}$ . The degree of unsaturation is calculated as follows:

Thus, compound B has 2 degrees of unsaturation, and it gives a reaction with dihydrogen in excess, in the presence of Pd-C.

 

In the following reaction, an alkane is formed. Thus, compound B contains one triple bond. 

The formula of compound C is $C_7{H}_{12}$ . The degree of unsaturation is calculated as follows:

Thus, compound C has two degrees of unsaturation, and it gives reaction with $NaN{H}_2 and C{H}_{3}I$.

 

In the following reaction, an alkyne with an extra methyl group is formed. Thus, compound C contains one triple bond. 

Structure of compound C