Question: (a) For a long time attempts to prepare compound A were thwarted by its ready isomerization to compound B. The isomerization is efficiently catalyzed by

(a) For a long time attempts to prepare compound A were thwarted by its ready isomerization to compound B. The isomerization is efficiently catalyzed by traces of base. Write a reasonable mechanism for this isomerization.

(b) Another attempt to prepare compound A by hydrolysis of its diethyl acetal gave only
the 1,4-dioxane derivative C. How was compound C formed?

HO OH Compound A Compound B CGHs O OH Compound C

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