Problem Set 8

1. Provide all possible products for the following reactions. Be sure to include all stereoisomers and consider
rearrangements.

HBr Br

POCl3 H 2O OH
H2SO4
OH

Et Cl
Et Cl
Cl2 Cl2

Cl Cl
+ enantiomer + enantiomer

Et Br
Et Br2 OH NBS
H2O H2O, DMSO OH
Br
+ enantiomer + enantiomer

1. BH3 1. BD3 D
OH CH3
2. H2O2 /OH- H 2. H2O2 /OH-
OH
+ enantiomer + enantiomer

D = Deuterium (a hydrogen with an extra neutron...shows the same reactivity as H)

1. Hg(OAc)2, H2O 1. Hg(OAc)2, H2O

CH3
2. NaBH4, H2O OH 2. NaBH4, H2O OH
+ enantiomer

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2. Complete the following reactions. Assume excess of all reagents. Provide all possible products, and consider
rearrangements.

PBr3 HBr Br
Br OH
rearranged product...

{OR}
POCl3
H2SO4
pyridine
H2O

H 1. BH3 H2SO4
OH
2. H2O2/ OH
- H2O
OH
+ enant

1. Hg(OAc)2, H2O
HCl
2. NaBH4, H2O

Cl

OH

O K

(= Br2/ H2O)

OH NBS
Br DMSO, H2O
+ enant. MAJOR

Cl2
NaH
H2O

HCl Cl OH
O
OH Cl
+ enant.

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