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Problem Set 8

1. The document provides a problem set involving organic reactions. It lists possible reactants and reagents and asks to identify all possible products, including stereoisomers and rearrangements. 2. Students are asked to complete several reactions by providing all possible products and considering rearrangements. Reactions include substitutions, additions, eliminations and other organic transformations. 3. The problem set requires the application of organic chemistry principles to predict and draw out reaction mechanisms and product structures in detail.

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CARLOS ALBERTO OSORIO MARTINEZ
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51 views2 pages

Problem Set 8

1. The document provides a problem set involving organic reactions. It lists possible reactants and reagents and asks to identify all possible products, including stereoisomers and rearrangements. 2. Students are asked to complete several reactions by providing all possible products and considering rearrangements. Reactions include substitutions, additions, eliminations and other organic transformations. 3. The problem set requires the application of organic chemistry principles to predict and draw out reaction mechanisms and product structures in detail.

Uploaded by

CARLOS ALBERTO OSORIO MARTINEZ
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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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

  1  
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.

  2  

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