This data comes from a lab that entailed the preparation of cyclohexene with cyc

Question

This data comes from a lab that entailed the preparation of cyclohexene with cyclohexanol as a regeant... this was via a acid catalyzed dehydration reaction using phosphoric acid.

I had a very high yeild because I did a poor distillation and I ended up getting a TON of toluene with my product. We checked the purity of the cyclohexene product using IR and NMR spectroscopy. I'm having a difficult time interpreting the results.

Thank you so much for your help!

4000 3500 26589 2734.0 29179 3025.3 2500 220 300 200 01.7 1856.8 1941.2 00 321.5 1379.1 5.7 1604.5 495.7 1523.5 600 Waenurnbers (crm 1) 1030.3 1106.6 1137.3 00 876.3 910A 00 641.1 694.4 728.7 600

Explanation / Answer

You have mixture of compounds.

IR: SP2 C-H stretch 3100 - 3000 cm- (coming from benzene and cyclo hexene)

SP3 C-H stretch 3000-2800 cm- (coming from cyclo hexene methylene groups and methyl in toluene)

1400 to 1600 cm- aromatic skeleton vibrations (coming from benzene group in toluene)

690 cm- and 720 cm- two peaks indicating mono substitution (methyl) on benzene. so indicates toluene.

NMR: You have 5 H of phenyl at 7.0 ppm

Cyclo hexene double bond protons (2H) at 5.9 ppm.

cyclo hexene methylen protons and methyl of tolune is coming around 1 to 3 ppm. Conclusion you are having toluene and cyclo hexene mixture of products from above data

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