Question

A tertiary alcohol H upon acid-catalyzed dehydration gives a product I. Ozonolysis of I leads to compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on reaction with KOH gives only M. What is the correct order of the reaction steps?

a) H→I→J→K→L→M
b) H→I→K→J→L→M
c) H→I→J→K→M→L
d) H→I→K→J→M→L

Answer 1

A tertiary alcohol undergoes acid-catalyzed dehydration to form an alkene. Ozonolysis of this alkene yields two distinct compounds that lead to different products when treated with KOH, suggesting different functional groups are present.

Step-by-step explanation:

In the sequence of reactions described, a tertiary alcohol undergoes acid-catalyzed dehydration to yield an alkene product I. Ozonolysis of this alkene yields compounds J and K, indicating that the alkene has distinct substituents on either end. Since compound J when reacted with KOH yields benzyl alcohol and another compound L, it suggests that J is likely to be an ester or a compound with a good leaving group next to a phenyl ring. Compound K, on the other hand, yields a single product M upon reaction with KOH, indicating that K is a simpler molecule, possibly a ketone or an aldehyde that could form a carboxylic acid or a salt upon treatment with a base like KOH.

The correct order of the reaction steps would involve the tertiary alcohol H being dehydrated to form the alkene I, followed by the ozonolysis of I to give compounds J and K. Compound J is then converted to benzyl alcohol and L when treated with KOH. Compound K reacts with KOH to give the product M. The detailed explanations provided by the summaries on oxidation and dehydration of alcohols are useful for understanding the variety of possible products from these reactions.