1 Chemistry 301 Fall. 2018 SIFP Problem Set 10 I. Identify the most likely product for each of the steps given by placing the appropriate compound letter in each of the circles provided; you may use a product only once. If the choice seems ambiguous, explain your thinking. H3CCH3OSCH3O OCH3NaITHFKOt-Bu THFNaCNCH2Cl2H3CCH3CNCH3H3CCH3CH3H3CCH3H3CCH3OMeCH3H3CCH3ICH3H3CCH3CNCH3H3CCH3H3CCH3CH3ABC DE FG HICH3IH3CCH3OMeCH3(racemic mixture)MeOHAgNO3H3CCH3CH3JOMeCGFII by Sn1. But B is possible by a Ag-assisted SN2 for partial credit.2 II. Predict the structure of the single most likely product (B) from the reaction of A upon stirring in ethanol solution. A. Draw the mechanism for the formation of B, showing all intermediates and label B. What is the name of this mechanism? B. Is the product B chiral? Yes No Cannot tell (circle correct answer) If yes, label each stereocenter as R or S. C. Explain your choice of mechanism (SN1, SN2, E1, E2) by comparing it with any one of the other (less favorable) mechanisms that could operate on A under these conditions. Since it is a substitution, the obvious comparison is with SN2. No strong nucleophile so reaction at the secondary position, while possible, is going to be very slow. Reaction at the tertiary position is prohibited. Both E1 and E2 are disfavored by the absence of base. Base is important in the product-determining step in competition with the SN1 D. On the chart here, draw the reaction coordinate diagram for the formation of B. Show all intermediates. Label the rate-determining transition state and draw a represenation of the transition state for this step. H3CCH3H3CBrBrEtOHroom temperatureAHB (C9H19BrO) + HBrH3CCH3H3CBrBrAHH3CCH3CH3BrH+ Br-HOEtH3CCH3H3COBrHHEtH3CCH3H3COBrHEt+ H+BSN1REreaction progressiiiBi =H3CCH3CH3BrHH3CCH3H3COBrHHEtii =rate-determining TSAH3CCH3H3CBrBrHδ+δ-rate-determining transition