Experiment 8: Multistep synthesis
Experiment 8: Multistep synthesis
Benzoin Condensation
O
H
+ CN- /H2O
OH OH H CN
O H
OH O H
OH CN
H
OHOH CN -
+ CN-
Since cyanide is quite toxic, we will use thiamine as our catalyst to replace cyanide
CH3
N
N
NH2 S
N +
CH3
ClOH
Thiamine is heat sensitive so the addition of 5 M NaOH needs to be added slowly (3 to 5 min) to the thiamine hydrochloride in an ice bath with constant swirling and maintain the temperature below room temperature.
Once the benzaldehyde is added, the reaction flask, an Erlenmeyer flask, is sealed with a cork and sealed with Parafilm to keep out air. Place in your drawer until next week.
How do I go about figuring out what my unknown is?
1. From your solubility measurements, you should be able to classify your unknowns according to the solubility classes discussed.
2. Complete and hand in your preliminary report if you haven't done so.
3. From your solubility measurements and you physical properties, make a list of the possible compounds.
4. Look up some reference IR spectra in your manual that have the possible functional groups present in your unknown.
5. Begin to analyze your NMR spectrum. If you have an carboxylic acid as an unknown, consider titrating it to determine its equivalent weight.
Step 2 Oxidation of benzoin to benzil
OH O H
HNO3
O
O
1. Run the reaction in the hood on a water bath (~95 ?C) 2. Recrystallize from 95 % ethanol and add a few drops of water
HNO3 + C14H12O2
C14H10O2 + NO2 + H2O
C14H12O2 C14 -8 HNO3 N+5 +1e-
C14H10O2 C14 -6
- 2e-
NO2
N+4
C14H12O2 2 HNO3 + 2 e-
2HNO3 + C14H12O2
C14H10O2 2 NO2
+ 2e-
C14H10O2 + 2NO2 + 2H2O
................
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