Question

Compound A has the molecular formula C9H12. Hydrogenation of compound A produces propylcyclohexane. Ozonolysis (ozone/water) of A produces a carboxylic acid and carbon dioxide. Hydroboration-oxidation(9BBN/hydrogen peroxide and sodium hydroxide) of compound A produces an aldehyde. Draw the structure of compound A and draw the structure of the acid produced from ozonolysis and the aldehyde produced upon hydroboration-oxidation of compound A.

Answer 1

First of all Formula should be C9H14 since during Ozonolysis and, Hydroboration-oxidation , alkene also involved and not possible to get desired products if it has C9H12. Since in C9H12 , there should be one more double bond. That means it has double bond inside the ring as it has double equivalent equal to 4 (1 triple bond(2 equivalents) 1 ring and 1 double bond). If it is C9H14, double bond equivalents are 3 ,correc cor matched with givrn structure.

Ozonolysis of terminal alkyne gives Carboxylic acid and CO2.

Hydroboration-oxidation of terminal alkyne gives aldehyde.