The molecule does not react with bromine in chloroform but can be brominated using bromine and FeBr3, and three different monobromo products are obtained.The number of H’s in the compound have to be a multiple of what integer? Explain your answer. The number of C’s in the compound have to be a multiple of what integer? What is the maximum number of C’s that can be in the compound? Explain how you determined the maximum number of C’s in the compound What functional groups are present in the compound (alkyl, aryl, ketone, etc.)? Explain your answer by referring to the information provided above. The Mass spec of the compound has a molecular ion peak at m/z = 178 and a base peak at m/z =178 (yes, the same value). The proton NMR showed the following:Signal Shift (ppm)Integration8.48.07.4ABCThere are four C-13 signals: 125, 126, 128, and 132 ppm. (A simple C13 chart is provided at theend of the exam.) The integrations for the four C13 peaks are 2:2:1:2 respectively.The IR Spectrum is presented below (black vertical line at 3000 cm¹ was drawn in):INFRARED SPECTRUMwwwwwwww0.80.60.4SplittingSinglet1Doublet2Doublet of Doublets 230002000Wavenumber (cm-1)1000

A question based on reactions of aromatic compounds and NMR spectroscopy. 3 subdivision questions…

Answered: The molecule does not react with…

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

Chapter14: Mass Spectrometry

Section: Chapter Questions

Problem 14.37P

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The molecule does not react with bromine in chloroform but can be brominated using bromine and FeBr3, and three different monobromo products are obtained.

The number of H’s in the compound have to be a multiple of what integer? Explain your answer.
The number of C’s in the compound have to be a multiple of what integer? What is the maximum number of C’s that can be in the compound? Explain how you determined the maximum number of C’s in the compound
What functional groups are present in the compound (alkyl, aryl, ketone, etc.)? Explain your answer by referring to the information provided above.

The Mass spec of the compound has a molecular ion peak at m/z = 178 and a base peak at m/z =
178 (yes, the same value). The proton NMR showed the following:
Signal Shift (ppm)
Integration
8.4
8.0
7.4
A
B
C
There are four C-13 signals: 125, 126, 128, and 132 ppm. (A simple C13 chart is provided at the
end of the exam.) The integrations for the four C13 peaks are 2:2:1:2 respectively.
The IR Spectrum is presented below (black vertical line at 3000 cm¹ was drawn in):
INFRARED SPECTRUM
wwwwwwww
0.8
0.6
0.4
Splitting
Singlet
1
Doublet
2
Doublet of Doublets 2
3000
2000
Wavenumber (cm-1)
1000

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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