Q.55. - Organic Chemistry

Question

Question: DHA is a fatty acid derived from fish oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid $\left[C{H}_3{\left(C{H}_2\right)}_{2}OC{O}_{2}H\right]$ and ozonolysis forms $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}\mathit{H}\mathit{O}\mathbf{,}\mathbf{ }\mathit{C}{\mathit{H}}_{\mathbf{2}}{\left(CHO\right)}_{\mathbf{2}}$ (five equivalents), and $\mathit{H}\mathit{C}\mathit{O}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}{\mathit{O}}_{\mathbf{2}}\mathit{H}$. What is the structure of DHA if all double bonds have the Z configuration?

Step-by-Step Solution

Answer

Answer

Step 1: DHA

DHA falls under the category of fatty acids and forms a major part of the human brain. It can be produced from alpha-linolenic acid or acquired directly from substances like fish oil, algae oil, etc.

Step 2: Hydrogenation

Molecular hydrogen fuses with another compound by utilizing catalysts like nickel and palladium, and this process is referred to as hydrogenation. Organic compounds can be reduced with the help of hydrogenation.

Step 3: Structure of DHA from the given reactants

The hydrogenation of DHA forms $C{H}_3{\left(C{H}_2\right)}_{20}COOH$, which indicates that DHA is a 22-carbon fatty acid. The carbonyl carbons of the products can be linked via a double bond to give the structure of DHA as:

Structure of DHA formed by linking the reactants