1. Predict the product(s) of the following reactions, noting stereochemistry where
appropriate and indicating when a racemic mixture of enantiomers is formed: (4
pts. each)
a.
1. NaCN, DMSO
Br
2. CH$_3$MgBr, ether; H$_3$O$^+$
CH$_3$
HgSO$_4$, H$_2$SO$_4$, H$_2$O
CH$_3$
b.
CH$_3$
c.
1. MCPBA, CH$_2$Cl$_2$
2. CH$_3$CH$_2$OH, H$^+$
CH$_3$
OCH$_2$CH$_3$
OH
racemic
d.
1. Br$_2$, hv
2. NaSCH$_3$, DMSO
CH$_3$
SCH$_3$
CH$_3$
racemic
e.
1. SO$_3$, H$_2$SO$_4$
2. Cl$_2$, AlCl$_3$
3. H$_3$O$^+$, heat
CH$_3$
CH$_3$
Cl