Final

Organic Chemistry 3

is over.

Check the solutions on the questions and answer that you have decided correctly

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Name or draw the following molecules:
 

 

- N,N-dimethylpent-2-ynamide

- (S,E)-4-bromo-3-methylpent-2-enal

- 2-ethyl-5-methylfuran

 

Provide the major product(s) of the following reactions:
 

Knowing the structure of L-(-)-Altrose, draw the Fisher projection and the skeletal structure (wedge projection) of D-(+)-Altrose.
Draw the Haworth projection of the pyranose form of D-(+)-Altrose.
 

D-(+)-Altrose is the enantiomer of L-(-)-Altrose.
To draw its Fisher projection, we only have to switch the absolute configuration of all its chiral centers:
 

 

Haworth projection of the pyranose form of D-(+)-Altrose:
 

Draw the structure of the missing compounds.
Draw the epimer of D-(+)-Glucose and D-(+)-Mannose where the sugars are converted to L-Sugars.
 

 

Epimer of D-(+)-Glucose and D-(+)-Mannose:
 

Draw the structure of compounds A, B, C, D and E.
 

Draw the structure of compounds A, B, C, D and give the missing synthetic conditions:
 

Give the structure of compounds A, B, C, D and E:
 

 

Propose a reasonable mechanisms for the following reaction:
 

Propose a reasonable mechanisms for the following reaction:
 

Propose a reasonable mechanisms for the following reaction:
 

Draw the 2 products of the following reaction and propose a reasonable mechanisms:
 

 

Note: For clarity, Br2 can be used in the mechanism instead of NBS

 

Mechanism: For clarity, Br2 is used in the mechanism instead of NBS
 

Propose a way to synthesize A from benzene and butane plus any other reagents containing at most one carbon atom or any inorganic reagents.
 

Propose a way to synthesize A from hexane-1,6-diol plus any other reagents containing at most one carbon atom or any inorganic reagents.