Researcher

Evan Curtin

Objective

To monitor the hydrolysis of benzalaniline in a (90:10) ethanol/water(vol) solution without using a deuterated solvent.

Procedure

0.184g benzalaniline was dissolved in 0.9mL ethanol (measured via a syringe)in an NMR tube. An HNMR was taken of this solution, after which 0.1mL water was added. HNMRs were taken 5 and 10 minutes after the addition of water. The NMR was taken by locking onto a tube of CDCl3, then replacing that tube with the sample and acquiring.

Results

Volume calculations







Discussion

After 10 minutes, it is unclear how much the imine hydrolyzed. The quality of the spectra makes it difficult to determine a ratio of imine to aldehyde, but there seems to be no more than around 10% hydrolysis over the time interval. To get more accurate readings, the experiment should be repeated with deuterated solvent (likely Methanol-d4)to help with the quality of the spectra. Additionally, more spectra should be taken to observe the reaction over a longer period of time.

Conclusion

Benzalaniline hydrolyzed no more than 10% in (90:10) ethanol/water(vol) after 10 minutes. The reaction can be monitored without a deuterated solvent, but the addition of one would help make the spectra and results more clear.

Log

14:17 - Weighed 0.0185g benzalaniline
14:20 - Added .9mL ethanol to benzalaniline (sample 1), transferred solution to NMR tube.
14:21 - Added CDCl3 to a separate NMR tube.
14:55 - Locked NMR to CDCl3, then removed and ran the scan on sample 1. This was done using a 500MHz varian NMR.
15:03 - Added 0.1mL water to sample 1 using a syringe.
15:08 - Took HNMR of sample 1 using same method as above.
15:13 - Took HNMR of sample 1, again with the same method.