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: Principles and Reactions
8th Edition
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:William L. Masterton, Cecile N. Hurley
Chapter18: Nuclear Reactions
Section: Chapter Questions
Problem 82QAP
icon
Related questions
icon
Concept explainers
Question
100%
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)
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning