Chapter 11, Problem 44CP

When a consumer purchases a tomato, smell is one of the factors affecting selection. Researchers in Japan have thus analyzed the volatile components of tomatoes using a novel method.¹¹ Among the complex mixture of 367 compounds detected were 3-methylbutanal and hexanal. Propose a single synthesis that produces an equimolar mixture of these two compounds (equal amounts of both products) starting with one $1^{\circ }$ alcohol, one $2^{\circ }$ alcohol, and one $3^{\circ }$ alcohol, each with fewer than six carbons. (Note that the designations $1^{\circ }$, $2^{\circ }$, and $3^{\circ }$ for alcohols are analogous to those of alkyl halides.)