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Acetophenone Reduction by Sodium Borohydride

1) The document describes a procedure for reducing acetophenone using sodium borohydride. Acetophenone and methanol are mixed and cooled in an ice bath. Sodium borohydride is then added to the mixture and stirred for 5-10 minutes. Thin layer chromatography is used to monitor the reaction. The product is extracted with dichloromethane and dried with sodium sulfate before evaporating the solvent. 2) Unreacted acetophenone may be present if insufficient sodium borohydride is used or if the reaction time is too short. 3) CH3CH2CHO would be reduced more rapidly because aldehydes undergo borohydride reduction faster

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Aravind Rao Karanam
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5K views2 pages

Acetophenone Reduction by Sodium Borohydride

1) The document describes a procedure for reducing acetophenone using sodium borohydride. Acetophenone and methanol are mixed and cooled in an ice bath. Sodium borohydride is then added to the mixture and stirred for 5-10 minutes. Thin layer chromatography is used to monitor the reaction. The product is extracted with dichloromethane and dried with sodium sulfate before evaporating the solvent. 2) Unreacted acetophenone may be present if insufficient sodium borohydride is used or if the reaction time is too short. 3) CH3CH2CHO would be reduced more rapidly because aldehydes undergo borohydride reduction faster

Uploaded by

Aravind Rao Karanam
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 DOCX, PDF, TXT or read online on Scribd
  • Acetophenone Reduction Procedure
  • Questions

Acetophenone Reduction by Sodium Borohydride

Procedure:
Weigh 1 g of Acetophenone into a clean 250 mL round bottom flask.
Add 14mL of MeOH and stir the solution using magnetic stirrer with the add of magnetic pellet.
Keep the reaction mixture in a ice bath to attain the temperature zero degree.
Now weigh around 0.35g of NaBH4 in a butter paper and add to the reaction mixture.
Continue the stirring for 5-10 minutes.
Monitor the progress of reaction using TLC. Spot both starting material as well as the reaction
mixture parallelly.
Elute the plate using ethyl acetate-Hexane eluent.(1:9)
Visualize the reactant and product spot with the UV lamp and mark with the dull pencil and dip in
2,4-dinitrophenyl hydrazine (2,4-DNP) stain. The ketone will show a faint orange spot.
Note: NEVER look directly at the light of this UV lamp, or your eyes could be severely
damaged. If you can see your sample on the plate using the UV light, you have enough.

Work up:
Remove the solvent using distillation set up.
Add water to the mixture and extracted with the DCM (Dichloromethane)
Finally dry the DCM layer using anhy. Sodium sulphate.
Evaporate DCM layer.
Take the weight of the RBF.

Clean Up
The TLC solvent mixtures should be placed in the organic waste bottles.
Check the pH of the EtOH/aqueous mixture; neutralize as needed and flush down the drain.








QUESTIONS :

1) Write an equation for the hydrolysis of NaBH4. The products should be NaH2BO3 and H2 gas.

2) Under what circumstances would you expect to find unreacted acetophenone in the product in
this experiment?

3) Which compound would you expect to undergo borohydride reduction more rapidly? Explain.
(a) CH3CH2CHO or (b) CH3CH2COCH2CH3

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