benzo.docx - Garrett Malave Organic Chemistry 222 – 511 Dr....

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Garrett MalaveOrganic Chemistry 222 – 511Dr. Friese11/5/19Synthesis of BenzodiazpineIn the lab last week, the starting material known as 1,2-diaminobenzene was converted tothe product known as 2,3-dihydro-2,2,4-trimethyl-1H-1,5-benzodiazpine through carbonylcondensation reactions involving acetone with sulfamic acid as a catalyst. This reaction replacesthe hydrogens on the amino group with the double bonds associated with acetone. As both aminogroups go through this reaction, a ring is formed with the electrons from each imine. Purificationof the desired product is done so through applications such as the separatory funnel, rotovap, andthe oven. The final product is confirmed through H NMR and IR analysis.The data presented in the H NMR provides significant evidence that our desired producthas been formed. The first signal present on the spectrum is a tall singlet peak at 1.55 ppm. Thissignal comes from the two methyl groups attached to the carbon ortho to the 2-degree amine(labeled 12 and 13). The reason for a singlet signal is because both CH3 groups containequivalent H’s and the nearest carbon contains no hydrogens, therefore no neighbors. The nextthree signals are also singlets. The first of the three singlet signals are the other methyl group,meta to the previous one (labeled 14). This provides a signal of 2.48 ppm and is a singlet because

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Term
Spring
Professor
Howard
Tags
Amine, Functional group, first signal present

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