Question

CONCEPT QUESTIONS (1) Instead of dropwise addition of anthranilic acid and isoamyl nitrite to the reaction vessel, a student adds all of their anthranilic acid and isoamyl nitrite in two portions. The remaining portion of the experiment is completed, and the student takes H NMR and 13C NMR spectra of their final solid, as shown below. 1H NMR Spectrum of Sample (300 MHz, DMSO, 25 °C) PPM 22H 13C NMR Spectrum of Sample (100 MHz, DMSO, 25 °C) 150 140 130 120 PPM

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Answer 1

Answers to the question 1 (a, b, c,and d oarts) have been explained as below.

1. The impusity structure from the above Treaction by InnaR & 13C NMR is confirmed as beloh. teos on=0 tem Deo amyl wotete Anthoantic aero TGO Benzyne Pupursty. Thus the thy formed benzyne can be used to the Diels-Alder reaction as the dienophile with other are reagent to gire 1, 2, 3, 4 tetaphenylhapthalene 1,2,3,4-teraphendrapthalene EBH. CN

PAULNU 6. Based on the ponded spectral information the ratio g 4 2, 3, 4 tetraphony napthalene to the benzyne impunity = 50% 24 from poronet - 100% = 2 as integrate 24 from impisity = 1 as integration = bxlco 50% impustty c) The impusity has high berling point thesefore it was enfront remove using sotarapour Borling point of benzyne As the benzyne impusity law therture it is very difficult to remove I by the prituration method during the pusitication of the product. O.