Chapter 18, Problem 8PP

Practice Problem 18.8

The acetoacetic ester synthesis generally gives best yields when primary halides are used in the alkylation step. Secondary halides give low yields, and tertiary halides give practically no alkylation product at all.

(a) Explain.

(b) What products would you expect from the reaction of sodioacetoacetic ester and tert-butyl bromide?

(c) Bromobenzene cannot be used as an arylating agent in an acetoacetic ester synthesis in the manner we have just described. Why not?