An optically active secondary alcohol X ( C ₅ H ₁₂ O ) undergoes acid-catalyzed dehydration to give alkene Y as the major product. Ozonolysis of Y yields a mixture of acetone and acetaldehyde. Reaction of X with acetyl chloride in the presence of pyridine gives an ester Z. Identify the IUPAC names of X, Y, and Z.

Step-by-step solution

Ozonolysis of alkene Y yields acetone ( CH ₃ COCH ₃ ) and acetaldehyde ( CH ₃ CHO ). Working backwards, joining the carbonyl carbons with a double bond gives Y as 2-methylbut-2-ene ( CH ₃- C ( CH ₃)= CH - CH ₃ ). Alcohol X ( C ₅ H ₁₂ O ) dehydrates to give Y as the major product. The possible alcohols are 2-methylbutan-2-ol and 3-methylbutan-2-ol. Since X is an optically active secondary alcohol, it must be the chiral 3-methylbutan-2-ol (which has a chiral center at C-2). Dehydration of 3-methylbutan-2-ol involves