11 8. When benzene is treated with Reagent(s) A followed by Reagent(s) B, Compound P (CaHCIO) is the major product. If the order of reagents is reversed, Compound Q (also Calf-CIO) is formed instead (see the scheme below). Both P and Q have a strong IR absorption around 1685 cm, H and "C NMR spectra of P and Q are shown below. Draw the structures of P and Q and list the Reagents A and B. Benzene 11 10 10 1. A 2. B Compound P ¹H NMR 2:2 Compound Q ¹H NMR ut 2:1:1 ppm ppm Benzene DEPT-90 DEPT-135 DEPT-90 DEPT-135 1. B 2. A 200 200 180 160 140 140 2² 2 peaks 120 120 ppm Compound P "C NMR 100 Compound Q 1³C NMR ppm 60 80 60 -9 -8

11 8. When benzene is treated with Reagent(s) A followed by Reagent(s) B, Compound P (CaHCIO) is the major product. If the order of reagents is reversed, Compound Q (also Calf-CIO) is formed instead (see the scheme below). Both P and Q have a strong IR absorption around 1685 cm, H and "C NMR spectra of P and Q are shown below. Draw the structures of P and Q and list the Reagents A and B. Benzene 11 10 10 1. A 2. B Compound P ¹H NMR 2:2 Compound Q ¹H NMR ut 2:1:1 ppm ppm Benzene DEPT-90 DEPT-135 DEPT-90 DEPT-135 1. B 2. A 200 200 180 160 140 140 2² 2 peaks 120 120 ppm Compound P "C NMR 100 Compound Q 1³C NMR ppm 60 80 60 -9 -8

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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