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Compound A of formula C7H3 ['HNMR & (ppm): 7.25-7.45 (m, 5H); 2.25 (s, 3H)] was treated with bromine and iron powder to give compound B. Compound B was treated with magnesium metal followed by ethyloxirane (butene-1,2-epoxide) and acidic workup gave product C whose IR spectrum shows intense broad band at 3400 cm-1. Treatment of C with Jones reagent gave D whose IR spectrum shows sharp, intense band at 1710 cm1. Your task is to: (a) Identify the structures of compounds A-D. (b) Sketch the proton NMR of compound D, with proper chemical shifts, multiplicities, and integration. (c) Sketch the carbon NMR of compound D, with proper chemical shifts. Note carbon NMR has no multiplicities or integration.

Compound A of formula C7H3 ['HNMR & (ppm): 7.25-7.45 (m, 5H); 2.25 (s, 3H)] was treated with bromine and iron powder to give compound B. Compound B was treated with magnesium metal followed by ethyloxirane (butene-1,2-epoxide) and acidic workup gave product C whose IR spectrum shows intense broad band at 3400 cm-1. Treatment of C with Jones reagent gave D whose IR spectrum shows sharp, intense band at 1710 cm1. Your task is to: (a) Identify the structures of compounds A-D. (b) Sketch the proton NMR of compound D, with proper chemical shifts, multiplicities, and integration. (c) Sketch the carbon NMR of compound D, with proper chemical shifts. Note carbon NMR has no multiplicities or integration.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Compound A of formula C7H3 ['HNMR & (ppm): 7.25-7.45 (m, 5H); 2.25 (s, 3H)] was treated with bromine and iron powder to give compound B. Compound B was treated with magnesium metal followed by ethyloxirane (butene-1,2-epoxide) and acidic workup gave product C whose IR spectrum shows intense broad band at 3400 cm-1. Treatment of C with Jones reagent gave D whose IR spectrum shows sharp, intense band at 1710 cm1. Your task is to: (a) Identify the structures of compounds A-D. (b) Sketch the proton NMR of compound D, with proper chemical shifts, multiplicities, and integration. (c) Sketch the carbon NMR of compound D, with proper chemical shifts. Note carbon NMR has no multiplicities or integration.
Transcribed Image Text:Compound A of formula C7H3 ['HNMR & (ppm): 7.25-7.45 (m, 5H); 2.25 (s, 3H)] was treated with bromine and iron powder to give compound B. Compound B was treated with magnesium metal followed by ethyloxirane (butene-1,2-epoxide) and acidic workup gave product C whose IR spectrum shows intense broad band at 3400 cm-1. Treatment of C with Jones reagent gave D whose IR spectrum shows sharp, intense band at 1710 cm1. Your task is to: (a) Identify the structures of compounds A-D. (b) Sketch the proton NMR of compound D, with proper chemical shifts, multiplicities, and integration. (c) Sketch the carbon NMR of compound D, with proper chemical shifts. Note carbon NMR has no multiplicities or integration.
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