1. For the following reactions, predict the major product. You do not need to provide a mechanism
although it may help you understand the reaction more thoroughly.
a.
H
1. NaCN, $H_2O$
H
OH
2. $H_2$, Pd-BaSO$_4$, HCl
HO
H
$H_2O$, 4 atm
H-
-OH
(two products)
OH
b.
OH
OH
H
OH
1. $H_2NOH$, pH 4-5, HCl(cat.)
2. Pyr
3. NaOCH$_3$, HOCH$_3$
C.
OH
1. NaOH, $H_2O$
0
2. $Br_2$, $H_2O$
H
OH
3. Fe$^{3+}$, $H_2O_2$, $H_2O$, CaCO$_3$
HO
H-
4. NaBH$_4$, $H_2O$
H
OH
5. $H_2O$, HCl
OH
d.
OH
1. PhOH, HCl, heat
HO
HO
OH
OH
2.
NaOH
$H_2CO-S-CH_3$
OH
HO
OCH$_3$
OH OH
(1 eq). HCl
(Hint: Acetal formation)