Researcher

Cuepil Choi

Objective

To whether diethylene glycol would react with 4-chlorobenzaldehyde at room temperature to form hemiacetals like it did with ethylene glycol to form hemiacetals. Also to examine what the ratio between aldehyde to hemiacetal would be with diethyelene glycol.

Procedure

A mixture of excess diethylene glycol and 4-chlorobenzaldehyde was added to a 1 dram vial and vortexed. Mixture was passed through a pasteur pipette with a kimtech filter. An HNMR was taken within an hour of making the mixture.

Results

HNMR spectrum 1 - after approximately 1 hr at 25 C

Discussion

The aldehyde may form an acetal after heating. Heat will have to be applied to see if the acetal will form. It is also interesting to consider whether the acetal will be cyclized or two branches of diethylene glycol.

Conclusion

The aldehyde reacted with diethylene glycol to form hemiacetals. No trace of acetals were found after the one hour period at room temperature.

Log

15:43 mass of 1 dram vial 4.5900 g
15:45 0.0756 of 4-chlorobenzaldehyde [put bottle label] added to 1 dram vial
15:50 1.3724 g of diethylene glycol added to 1 dram vial
16:00 vortexed mixture for about 5 minutes
16:00 insolubility event.
16:05 mixture passed through kimtech filter
16:08 pipetted into HNMR tube with D2O in outer tube
16:55 HNMR 1 taken