The following sequence of reactions was used to synthesis compound F. Compound B, which is produced in step 2, is used in the fifth step. In step 5, B is de-protonated by NaOCH3 in an acid-base reaction and reacted with D in a substitution reaction (a small amount of alkene is also formed in this reaction which should be ignored). In the first step, only one isomer, A, is formed. Compound F yielded as a pair of enantiomers.
For each of the six reactions, draw the major product (A-F) of the reaction. Show all stereoisomers of A-F which are formed. When the starting material consists of several stereoisomers, clearly indicate the stereoisomer of the product formed from each of the stereoisomers of the starting material.
Draw the accepted mechanism for each reaction and illustrate how each stereoisomer is formed in the reaction. For the reaction, which yields product B, predict the peaks in the IR and NMR spectra of the starting material and the product B. Also comment on the differences in these spectra which indicate a successful reaction yielding the product.
