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A old house. The bottle was labelled information was given, but inside the bottle were some white crystals. student found a bottle of unknown origin in the basement of an “CAUTION—contains C₁H₁O." No other 12 16 The student took the bottle to a chemistry laboratory, where she analyzed the crystals with the help of the laboratory staff. C₁H₁6O reacted with Br₂ in CCl4, adding one mole of Br, and forming C₁2H₁OB₂. 16 When a sample of C₁H₂O was reacted with O3 followed by Zn/H₂O, two 16 different samples, J and K, were obtained. Compound J had a molecular formula of CH₂O₂, and its NMR is shown below. Compour | K had a molecular formula of C₂HÃO, and it could be oxidized to compound L, with a molecular formula of C₂H§O₂. The IR spectrum of L showed a very wide, strong band centred around 3000 cm³¹. The NMR spectrum of L showed only two different absorptions: a doublet (6H) at 0.9 ppm and a septet (1H) at 3.6 ppm. There was also a singlet (1H) off the scale at 11.8 ppm. students, deduce possible structures for J, K, and L, as As fellow well as for C₂₂H₁6O. NMR SPECTRUM OF “J” (CÂHgO₂) 10 + 9 8 7 6 5 4 3 + 3 + 2 1 0 (ppm)

A old house. The bottle was labelled information was given, but inside the bottle were some white crystals. student found a bottle of unknown origin in the basement of an “CAUTION—contains C₁H₁O." No other 12 16 The student took the bottle to a chemistry laboratory, where she analyzed the crystals with the help of the laboratory staff. C₁H₁6O reacted with Br₂ in CCl4, adding one mole of Br, and forming C₁2H₁OB₂. 16 When a sample of C₁H₂O was reacted with O3 followed by Zn/H₂O, two 16 different samples, J and K, were obtained. Compound J had a molecular formula of CH₂O₂, and its NMR is shown below. Compour | K had a molecular formula of C₂HÃO, and it could be oxidized to compound L, with a molecular formula of C₂H§O₂. The IR spectrum of L showed a very wide, strong band centred around 3000 cm³¹. The NMR spectrum of L showed only two different absorptions: a doublet (6H) at 0.9 ppm and a septet (1H) at 3.6 ppm. There was also a singlet (1H) off the scale at 11.8 ppm. students, deduce possible structures for J, K, and L, as As fellow well as for C₂₂H₁6O. NMR SPECTRUM OF “J” (CÂHgO₂) 10 + 9 8 7 6 5 4 3 + 3 + 2 1 0 (ppm)

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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student found a bottle of unknown origin in the basement of an "CAUTION—contains С₁H₁O.” No other A old house. The bottle was labelled information was given, but inside the bottle were some white crystals. The student took the bottle to a chemistry laboratory, where she analyzed the crystals with the help of the laboratory staff. C₁2H₁6O reacted with Br₂ in CCl4 adding one mole of Br, and forming C₁₂H₁OB2₂. When a sample of C₁₂H₂O was reacted with O3 followed by Zn/H₂O, two different samples, J and K, were obtained. Compound J had a molecular formula of C.HgO₂, and its NMR is shown below. Compound K had a molecular formula of C₂H₂O, and it could be oxidized to compound L, with a molecular formula of C₂H₂O₂. The IR spectrum of L showed a very wide, strong band centred around 3000 cm*¹. The NMR spectrum of L showed only two different absorptions: a doublet (6H) at 0.9 ppm and a septet (1H) at 3.6 ppm. There was also a singlet (1H) off the scale at 11.8 ppm. students, deduce possible structures for J, K, and L, as As fellow well as for C₁2H₁6O. NMR SPECTRUM OF “J” (CÂHgO₂) 10 9 8 4 7 + 6 5 + 4 3 + 3 + 2 1 0 (ppm)
Transcribed Image Text:student found a bottle of unknown origin in the basement of an "CAUTION—contains С₁H₁O.” No other A old house. The bottle was labelled information was given, but inside the bottle were some white crystals. The student took the bottle to a chemistry laboratory, where she analyzed the crystals with the help of the laboratory staff. C₁2H₁6O reacted with Br₂ in CCl4 adding one mole of Br, and forming C₁₂H₁OB2₂. When a sample of C₁₂H₂O was reacted with O3 followed by Zn/H₂O, two different samples, J and K, were obtained. Compound J had a molecular formula of C.HgO₂, and its NMR is shown below. Compound K had a molecular formula of C₂H₂O, and it could be oxidized to compound L, with a molecular formula of C₂H₂O₂. The IR spectrum of L showed a very wide, strong band centred around 3000 cm*¹. The NMR spectrum of L showed only two different absorptions: a doublet (6H) at 0.9 ppm and a septet (1H) at 3.6 ppm. There was also a singlet (1H) off the scale at 11.8 ppm. students, deduce possible structures for J, K, and L, as As fellow well as for C₁2H₁6O. NMR SPECTRUM OF “J” (CÂHgO₂) 10 9 8 4 7 + 6 5 + 4 3 + 3 + 2 1 0 (ppm)
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