When pseudoionone is treated with BF3 in acetic acid, ring closure takes place and a-

Chapter 19, Problem 19.13

(choose chapter or problem)

When pseudoionone is treated with BF3 in acetic acid, ring closure takes place and a- and b-ionone are produced. This is the next step in the vitamin A synthesis. O Pseudoionone BF3 HOAc O -Ionone O -Ionone (a) Write mechanisms that explain the formation of a- and b-ionone. (b) b-Ionone is the major product. How can you explain this? (c) Which ionone would you expect to absorb at longer wavelengths in the UVvisible region? Why?

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