1. (a) Discuss why the transformation shown below will not produce the product shown.

Be sure to include any applicable discussion on choices of reagents,

regioselectivity and stereochemical outcome expected versus what is shown in the product.

(b) Propose a way to fix the conditions so that the desired product provided can be made from the

substrate given. You can do this simply by constructing a new scheme. Be sure to show the correct

reagents/conditions for each step and make sure that each step is in the correct order. If applicable,

the proposed fix should also consider both the regio- and stereochemistry shown in the desired

product. There may be more steps required than the number originally shown for the

transformation. You will need to recall knowledge of both current and previous reactions

presented in organic chemistry I & II.

reagents/ conditions OH A. 1. OsO4, H,0 2. NaSH + enantiomer SH desired product substrate