The compound 5,9,12,16-tetramethyleicosane was synthesized as part of a study of the
Chapter 13, Problem 13.71(choose chapter or problem)
The compound 5,9,12,16-tetramethyleicosane was synthesized as part of a study of the male sex pheromone of a Brazilian bug that feeds on the leaves and fruit of tomato plants (J. Chem. Ecol. 2012, 38, 814 824). The synthesis of this alkane was reported using compounds AC. O Br O A B C O 5,9,12,16-Tetramethyleicosane A key step in the synthesis is shown below, in which a mixture of E and Z isomers is obtained: OH HBr Br (a) Draw a plausible mechanism for this process. (b) Propose an efficient synthesis of 5,9,12,16-tetramethyleicosane using A, B, and C as your only sources of carbon.
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