Consider the following compound: (a) Develop all reasonable retrosynthetic analyses for

Chapter 7, Problem 5

(choose chapter or problem)

Consider the following compound: (a) Develop all reasonable retrosynthetic analyses for this compound (any diastereomer) that, at some point, involve carboncarbon bond formation by alkylation of an alkynide ion. (b) Write reactions, including reagents and conditions, for syntheses of this compound that correspond to the retrosynthetic analyses you developed above. (c) Infrared spectroscopy could be used to show the presence of certain impurities in your final product that would result from leftover intermediates in your syntheses. Which of your synthetic intermediates would show IR absorptions that are distinct from those in the final product, and in what regions of the IR spectrum would the absorptions occur? (d) Draw a three-dimensional structure for either the cis or trans form of the target molecule. Use dashed and solid wedges where appropriate in the alkyl side chain and use a chair conformational structure for the ring. (Hint: Draw the structure so that the carbon chain of the most complicated substituent on the cyclohexane ring and the ring carbon where it is attached are all in the plane of the paper. In general, for three-dimensional structures choose an orientation that allows as many carbon atoms as possible to be in the plane of the paper.)