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5. Consider the following nitration reactions. Note that the nitration of N,N-dimethylaniline (shown in part 5c) contrasts in some ways the nitration of isopropylbenzene under the same conditions. 5a. The reaction of isopropylbenzene under nitration conditions (HNO3 and H*) is greatly accelerated by increased acid concentration. Explain why this rate acceleration is observed in terms of the mechanism of nitration 5b. In the reaction of isopropylbenzene under nitration conditions (HNO3 and H*), one mono-nitro product is predominant under all conditions. What is the structure of this product and why is it favored in this reaction. Show the complete mechanism and specify the rate-determining step. 5c. The reaction of N,N-dimethylaniline under nitration conditions (HNO3 and H) actually slows down as the acid concentration is increased AND the selectivity begins to favor the formation of the meta isomer at high acid concentration. Explain the change in rate and regioselectivity in terms of the mechanism of N,N-dimethylaniline this reaction. N(CH3)2 HNO3 acid N(CH₂)2 NO₂

5. Consider the following nitration reactions. Note that the nitration of N,N-dimethylaniline (shown in part 5c) contrasts in some ways the nitration of isopropylbenzene under the same conditions. 5a. The reaction of isopropylbenzene under nitration conditions (HNO3 and H*) is greatly accelerated by increased acid concentration. Explain why this rate acceleration is observed in terms of the mechanism of nitration 5b. In the reaction of isopropylbenzene under nitration conditions (HNO3 and H*), one mono-nitro product is predominant under all conditions. What is the structure of this product and why is it favored in this reaction. Show the complete mechanism and specify the rate-determining step. 5c. The reaction of N,N-dimethylaniline under nitration conditions (HNO3 and H) actually slows down as the acid concentration is increased AND the selectivity begins to favor the formation of the meta isomer at high acid concentration. Explain the change in rate and regioselectivity in terms of the mechanism of N,N-dimethylaniline this reaction. N(CH3)2 HNO3 acid N(CH₂)2 NO₂

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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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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5. Consider the following nitration reactions. Note that the nitration of N,N-dimethylaniline (shown in part 5c) contrasts in some ways the nitration of isopropylbenzene under the same conditions. 5a. The reaction of isopropylbenzene under nitration conditions (HNO3 and H*) is greatly accelerated by increased acid concentration. Explain why this rate acceleration is observed in terms of the mechanism of nitration 5b. In the reaction of isopropylbenzene under nitration conditions (HNO3 and H*), one mono-nitro product is predominant under all conditions. What is the structure of this product and why is it favored in this reaction. Show the complete mechanism and specify the rate-determining step. 5c. The reaction of N,N-dimethylaniline under nitration conditions (HNO3 and H) actually slows down as the acid concentration is increased AND the selectivity begins to favor the formation of the meta isomer at high acid concentration. Explain the change in rate and regioselectivity in terms of the mechanism of N,N-dimethylaniline this reaction. N(CH3)2 HNO3 acid N(CH3)2 NO₂
Transcribed Image Text:5. Consider the following nitration reactions. Note that the nitration of N,N-dimethylaniline (shown in part 5c) contrasts in some ways the nitration of isopropylbenzene under the same conditions. 5a. The reaction of isopropylbenzene under nitration conditions (HNO3 and H*) is greatly accelerated by increased acid concentration. Explain why this rate acceleration is observed in terms of the mechanism of nitration 5b. In the reaction of isopropylbenzene under nitration conditions (HNO3 and H*), one mono-nitro product is predominant under all conditions. What is the structure of this product and why is it favored in this reaction. Show the complete mechanism and specify the rate-determining step. 5c. The reaction of N,N-dimethylaniline under nitration conditions (HNO3 and H) actually slows down as the acid concentration is increased AND the selectivity begins to favor the formation of the meta isomer at high acid concentration. Explain the change in rate and regioselectivity in terms of the mechanism of N,N-dimethylaniline this reaction. N(CH3)2 HNO3 acid N(CH3)2 NO₂
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