Question

\((10 E, 12 Z)-10,12\)-hexadecadien-1-ol is a sex pheromone of the silkworm. Draw a structural formula for this compound.

Short answer

Question: Draw the structural formula for the compound (10 E, 12 Z)-10,12-hexadecadien-1-ol, which is a sex pheromone of the silkworm, and describe its main features. Answer: The structural formula for (10 E, 12 Z)-10,12-hexadecadien-1-ol is a linear chain of 16 carbon atoms, with a hydroxyl group (-OH) at the 1st carbon, the first double bond at the 10th carbon with an E configuration, and the second double bond at the 12th carbon with a Z configuration. The E configuration means that the two largest groups on each carbon atom are on the opposite sides of the double bond, while the Z configuration means that the two largest groups on each carbon atom are on the same side of the double bond. The carbon atoms are filled with hydrogen atoms so that each carbon has a total of four bonds. 

Step-by-step solution

Identify the main carbon chain

The name hexadecadien-1-ol suggests that the compound is an alcohol, owing to the "-ol" ending. Hexadeca- indicates that the main carbon chain has 16 carbon atoms. Additionally, "dien" means two double bonds are present within the structure.

Determine the location of double bonds and hydroxyl group

\((10 E, 12 Z)-10,12\)-hexadecadien-1-ol indicates that the first double bond is in the 10th carbon, with an E configuration, and the second double bond is in the 12th carbon with a Z configuration. The hydroxyl group (-OH) is located at the 1st carbon.

Draw the main carbon chain

Draw a linear chain of 16 carbon atoms, labelling them from 1 to 16. The 1st carbon will have the hydroxyl group (-OH) attached.

Draw the double bonds with the correct configurations

At the 10th carbon, draw an E double bond, which means that the two largest groups on each carbon atom are on the opposite sides of the double bond. At the 12th carbon, draw a Z double bond, which means that the two largest groups on each carbon atom are on the same side of the double bond.

Complete the structural formula

Fill in the remaining carbon atoms with hydrogen atoms to complete the structure of the compound. Each carbon should follow the rules of bonding and have four bonds in total. The structural formula for \((10 E, 12 Z)-10,12\)-hexadecadien-1-ol is: