Question

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

Short answer

From the compound Z, the uncertainty in the arrangement of groups around C=C (either E or Z configuration) cannot be determined.

Step-by-step solution

Alkynes

Compounds comprising carbon-carbon triple bonds are termed alkynes. Certain plants and insects use alkynes to protect themselves from various diseases. An alkyne named as parsalmide is employed as an analgesis.

Ozonolysis

Carboxylic acids are acquired as products when alkynes are subjected to ozonolysis followed by hydrolysis. The triple bond position in an unfamiliar alkane can be decided by ozonolysis.

Identification of compound Z from the products formic acid, 3-oxobutanoic acid, and hexanal

The treatment of compound, 4-Methyl-4-decen-1-yne with ozone leads to the formation of formic acid, 3-oxobutanoic acid, and hexanal as products. The reaction can be given as:

Structure of compound Z from the given products

Hence, the compound (Z) is 4-Methyl-4-decen-1-yne.

From the compound Z, the uncertainty in the arrangement of groups around C=C (either E or Z configuration) cannot be determined.