A student performed a series of reactions and obtained the spectral data provided. Thereaction sequence is shown below.. What are the structures for A, B, C, and D?Compound B NMR (relative integrated areas below peaks)CH;CH,O°N1. BHTHFN-bromosuccnimideACH;CH,OHB2. H,O,/OH-DhvrefluxCompound A NMR (relative integrated areas below peaks)PPM5Compound B IRINFRARED SPECTRUMPPM5160.8Compound A IRINFRARED SPECTRUM0.60.80.40.40.2-30002000Wavenumber (cm-1)1000The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relativeabundance of 1:0.972000Wavenumber (cm-1)30001000TransmitanceRelative Transmittance Compound C NMR (relative integrated areas below peaks)Compound D NMR (relative integrated areas below peaks)PPMPPM321 134 111 113Compound C IRPeak at 4.6 disappears when Dr0 is added to sample.INFRARED SPECTRUMCompound D IR (Gas Phase)INFRARED SPECTRUM0.80.990.60.980.40.970.23000200010000.96Wavenumber (cm-1)300020001000Wavenumber (cm-1)Peak at 3700 cm' is much stronger & broader in liquid phase.Relative TransmittanceRelative Transmittance

The structure of compound A, B, C and D are needed t be predicted using the given NMR data and the…

A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH,CH,O'Na N-bromosuccinimide A I. BIH/THF 2. HO/OH D CH;CH,OH hv reflux Compound A NMR (relative integrated areas below peaks) 3 PPM 5 6. Compound B IR INFRARED SPECTRUM 3 PPM 5 1 0.8 Compound A IR INFRARED SPECTRUM 0.6- 0.8 0.4 0.4 0.2 3000 2000 1000 Wavenumber (cm-1) The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 3000 2000 Wavenumber (cm-1) 1000 Transmitance Relative Transmittance

A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH,CH,O'Na N-bromosuccinimide A I. BIH/THF 2. HO/OH D CH;CH,OH hv reflux Compound A NMR (relative integrated areas below peaks) 3 PPM 5 6. Compound B IR INFRARED SPECTRUM 3 PPM 5 1 0.8 Compound A IR INFRARED SPECTRUM 0.6- 0.8 0.4 0.4 0.2 3000 2000 1000 Wavenumber (cm-1) The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 3000 2000 Wavenumber (cm-1) 1000 Transmitance Relative Transmittance

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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Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

A student performed a series of reactions and obtained the spectral data provided. The
reaction sequence is shown below.. What are the structures for A, B, C, and D?
Compound B NMR (relative integrated areas below peaks)
CH;CH,O°N
1. BHTHF
N-bromosuccnimide
A
CH;CH,OH
B
2. H,O,/OH-
D
hv
reflux
Compound A NMR (relative integrated areas below peaks)
PPM
5
Compound B IR
INFRARED SPECTRUM
PPM
5
1
6
0.8
Compound A IR
INFRARED SPECTRUM
0.6
0.8
0.4
0.4
0.2-
3000
2000
Wavenumber (cm-1)
1000
The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative
abundance of 1:0.97
2000
Wavenumber (cm-1)
3000
1000
Transmitance
Relative Transmittance

Compound C NMR (relative integrated areas below peaks)
Compound D NMR (relative integrated areas below peaks)
PPM
PPM
3
2
1 1
3
4 1
1
1 1
1
3
Compound C IR
Peak at 4.6 disappears when Dr0 is added to sample.
INFRARED SPECTRUM
Compound D IR (Gas Phase)
INFRARED SPECTRUM
0.8
0.99
0.6
0.98
0.4
0.97
0.2
3000
2000
1000
0.96
Wavenumber (cm-1)
3000
2000
1000
Wavenumber (cm-1)
Peak at 3700 cm' is much stronger & broader in liquid phase.
Relative Transmittance
Relative Transmittance

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