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Organic Chemistry Problem Set #9

This document contains a problem set involving naming organic compounds, proposing synthetic routes using acetylide reactions, devising syntheses, and completing organic reactions. The problem set covers topics such as substitution, elimination, addition, oxidation, and reduction reactions as well as naming alkynes, alkenes, and haloalkanes. Students are asked to apply their understanding of functional group interconversions and multi-step synthesis.

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CARLOS ALBERTO OSORIO MARTINEZ
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36 views3 pages

Organic Chemistry Problem Set #9

This document contains a problem set involving naming organic compounds, proposing synthetic routes using acetylide reactions, devising syntheses, and completing organic reactions. The problem set covers topics such as substitution, elimination, addition, oxidation, and reduction reactions as well as naming alkynes, alkenes, and haloalkanes. Students are asked to apply their understanding of functional group interconversions and multi-step synthesis.

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.
Available Formats
Download as PDF, TXT or read online on Scribd

Problem Set #9

1.  Name  the  following  compounds:  


a.           b.  
 
Br
Br

Br          
 
4,5,6  tribromo  2  hexyne                                                  4,6  dimethyl  1  cyclooctyne  
 
c.           d.  

         
 
     3  methyl,  1,5  heptadiyne                                                        4  penten1yne  
 
 
2.  What  are  the  two  ways  each  compound  could  be  made  via  acetytilide  reactions?  
 
NaNH2 CH3I NaNH2

CH3CH2I

NaNH2 CH3I NaNH2

Br

NaNH2 Br NaNH2

Br

 
 

3.  Devise  a  synthesis  for  the  following  molecules:  


 
 
Br
Br Br

Br Br Br

NaNH2
2 eq
2Br2

 
 
 
 
 
O

NaNH2 1. BH3
2. H2O2, _OH
CH3I
 
 
 
 
 
 
 
 
Br

NaNH2 NaNH2
2 eq

Br
Br2
Br  
 
 
 
4. Complete the following reactions:

Br Ph
O HO
1.
Ph

SN2 2. H2O

NaH
or NaNH2
In the IR spectrum of
1-butyne, where will the
C=C stretch appear?
Cl Cl
2 Cl2
H H
Cl Cl
1. BH3
2. H2O2, OH-
2 HBr

Br H O
H H
OH
Br H
H

NaH
or NaNH2

O
H2SO4
H3C CH3
HgSO4
H 2O
OH

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