Reaction of compound A (molecular formula = C₁₂H₂₂)with ozone followed by reaction with DMS produces only (CH₃)₃CCH₂CHO.Which of the following could be compound A?

Question

Quizplus · Accepted Answer

The given product, (CH₃)₃CCH₂CHO, is the ozonolysis product of an alkene followed by reaction with DMS. This indicates that compound A is an alkene. Moreover, the presence of two carbonyl groups in the product indicates that the original alkene must have had two double bonds. Among the given options, only compound D, cis-2,2,7,7-tetramethyloct-4-ene, has two double bonds as required. The ozonolysis of this compound would give two ozonide fragments, one containing a carbonyl and a methyl group, and the other containing a carbonyl and a dimethyl group. Reaction of these fragments with DMS would then produce the given product. Therefore, compound D could be the only option for compound A.

Reaction of Compound a (Molecular Formula = C12H22)with Ozone Followed

Reaction of Compound a (Molecular Formula = C₁₂H₂₂)with Ozone Followed