Propanal is treated with CH3MgBr and then H3O+ to give A. A is heated with concentrated H2SO4 to give the major alkene B. B is subjected to ozonolysis followed by Zn/H2O. The organic product(s) is/are

JEE Advanced levelSingle correct optionDifficulty 3 of 3si145

Propanal is treated with $CH X_{3} MgBr$ and then $H X_{3} O X^{+}$ to give A. A is heated with concentrated $H X_{2} SO X_{4}$ to give the major alkene B. B is subjected to ozonolysis followed by $Zn / H X_{2} O$ . The organic product(s) is/are

A is butan-2-ol,

CH X_{3} CH (OH) CH X_{2} CH X_{3}

. Acid-catalysed dehydration gives the more substituted (Saytzeff) alkene but-2-ene as the major product. Reductive ozonolysis of

CH X_{3} CH = CHCH X_{3}

gives two molecules of

CH X_{3} CHO

and no other product. Ethanoic acid would need oxidative work-up.