5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example, Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times). The synthesis of TNT starting with toluene (PhCH,) is straightforward even if the isolation of the final product requires careful planning and a gentle touch (otherwise, KABOOM!). Answer the following questions about the synthesis of TNT starting with toluene. a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts] b. Structures I-III are the possible isomers after the addition of a single nitro group. Which isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu- ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts] A I alone B II alone O₂N O₂N NO₂ II III C III alone E I and III D I and II F II and III c. Structures a-f are the possible isomers after the addition of two nitro groups. Which isomers are the major reaction intermediates after addition of two nitro groups to toluene? Write the letter (A-1) corresponding to your answer in the box. [3 pts] O₂N O₂N. O₂N O₂N. NO₂ O₂N NO₂ O₂N A a a and b B a and e C b and c NO₂ b NO₂ O₂N NO₂ e D b and d G c and f E c and d H d and f F c and e e and f Stuctures 1-5 are the possible isomers of TNT. Use the numbered structures to answer the re- maining three parts to this question about TNT. O₂N NO₂ 1 2 O₂N. NO₂ NO₂ NO₂ NO₂ NO₂ 5 3 d. Which isomer is the dominant product after the addition of three nitro groups to toluene? Write the number (1-5) corresponding to your answer in the box. [3 pts] Predict the 'H NMR spectra of the isomers of TNT (1-5). Focus on: • What are the relative integrations of the methyl and aromatic protons? ⚫ Are the aromatic protons equivalent or not? • What are the splitting patterns of the methyl and aromatic protons? Use that information to answer which isomers-if any-match the 'H NMR spectra given in parts e and f. Use the following choices to answer both parts e and f. A 1 alone B 3 alone с 1 and 4 D 2 and 5 E 3 and 4 F No isomer would give this spectrum. e. Which TNT isomer(s) match(es) the 'H NMR spectrum given below? Write the letter (A-F) corresponding to your answer in the box. [3 pts] f. Which TNT isomer(s) match(es) the 1H NMR spectrum given below? Write the letter (A-F) corresponding to your answer in the box. [2 pts] 2H 10 8, ppm 3H 2H 8, ppm 3H

5. Trinitrotoluene or TNT is, perhaps, the best-known explosive (in classic cartoons, for example, Wile E. Coyote unsuccessfully employs TNT against the Roadrunner many times). The synthesis of TNT starting with toluene (PhCH,) is straightforward even if the isolation of the final product requires careful planning and a gentle touch (otherwise, KABOOM!). Answer the following questions about the synthesis of TNT starting with toluene. a. Name the reagent(s) required to add the nitro groups to toluene. [2 pts] b. Structures I-III are the possible isomers after the addition of a single nitro group. Which isomer(s) is/are the major reaction intermediates after addition of the first nitro group to tolu- ene? Write the letter (A-F) corresponding to your answer in the box. [3 pts] A I alone B II alone O₂N O₂N NO₂ II III C III alone E I and III D I and II F II and III c. Structures a-f are the possible isomers after the addition of two nitro groups. Which isomers are the major reaction intermediates after addition of two nitro groups to toluene? Write the letter (A-1) corresponding to your answer in the box. [3 pts] O₂N O₂N. O₂N O₂N. NO₂ O₂N NO₂ O₂N A a a and b B a and e C b and c NO₂ b NO₂ O₂N NO₂ e D b and d G c and f E c and d H d and f F c and e e and f Stuctures 1-5 are the possible isomers of TNT. Use the numbered structures to answer the re- maining three parts to this question about TNT. O₂N NO₂ 1 2 O₂N. NO₂ NO₂ NO₂ NO₂ NO₂ 5 3 d. Which isomer is the dominant product after the addition of three nitro groups to toluene? Write the number (1-5) corresponding to your answer in the box. [3 pts] Predict the 'H NMR spectra of the isomers of TNT (1-5). Focus on: • What are the relative integrations of the methyl and aromatic protons? ⚫ Are the aromatic protons equivalent or not? • What are the splitting patterns of the methyl and aromatic protons? Use that information to answer which isomers-if any-match the 'H NMR spectra given in parts e and f. Use the following choices to answer both parts e and f. A 1 alone B 3 alone с 1 and 4 D 2 and 5 E 3 and 4 F No isomer would give this spectrum. e. Which TNT isomer(s) match(es) the 'H NMR spectrum given below? Write the letter (A-F) corresponding to your answer in the box. [3 pts] f. Which TNT isomer(s) match(es) the 1H NMR spectrum given below? Write the letter (A-F) corresponding to your answer in the box. [2 pts] 2H 10 8, ppm 3H 2H 8, ppm 3H

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

Chapter7: Alkynes

Section: Chapter Questions

Problem 7.19P

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