C._ ~ HBr ether Br Br✗ 12 15. In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C,H₁₂2" Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen; and, after treatment with acidic KMnO4, Compound A gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO4. O FO HO-C-CHCH2CH2CH2-C-OH CH₁₂ Compound C cyclohexanone A. How many degrees of unsaturation does Compound A possess? C₁ Hız B. Suggest structures for A and B. T 1-(12/2)+ unsaturated

Chemistry by OpenStax (2015-05-04)
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Chapter18: Representative Metals, Metalloids, And Nonmetals
Section: Chapter Questions
Problem 115E: A mixture of xenon and ?uorine was heated. A sample of the white solid that formed reacted with...
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C._
~
HBr
ether
Br
Br✗
12
15. In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the
label "Compound A: C,H₁₂2" Government agents have offered you a considerable sum to
determine the structure of this compound. After verifying the molecular formula by elemental
analysis, you find that Compound A reacts with 1 mol equiv of hydrogen; and, after treatment
with acidic KMnO4, Compound A gives the dicarboxylic acid C (see below). Another bottle
from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts
with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO4.
O
FO
HO-C-CHCH2CH2CH2-C-OH
CH₁₂
Compound C
cyclohexanone
A. How many degrees of unsaturation does Compound A possess? C₁ Hız
B. Suggest structures for A and B.
T
1-(12/2)+
unsaturated
Transcribed Image Text:C._ ~ HBr ether Br Br✗ 12 15. In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C,H₁₂2" Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen; and, after treatment with acidic KMnO4, Compound A gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO4. O FO HO-C-CHCH2CH2CH2-C-OH CH₁₂ Compound C cyclohexanone A. How many degrees of unsaturation does Compound A possess? C₁ Hız B. Suggest structures for A and B. T 1-(12/2)+ unsaturated
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