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

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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
Transcribed Image Text: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
Transcribed Image Text: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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