Chapter 13: Q13.44E (page 419)
Propose structures for compounds that fit the following NMR data:
(a) C5H10O
0.95(6H,double, J = 7Hz)
2.10(3H,singlet)
2.43(1H, mutiplet)
(b) C3H5Br
2.32(3H,singlet)
5.35 (3H,singlet)
5.45(1H, broad signet )
Chapter 13: Q13.44E (page 419)
Propose structures for compounds that fit the following NMR data:
(a) C5H10O
0.95(6H,double, J = 7Hz)
2.10(3H,singlet)
2.43(1H, mutiplet)
(b) C3H5Br
2.32(3H,singlet)
5.35 (3H,singlet)
5.45(1H, broad signet )
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Get started for freeQuestion: When measured on a spectrometer operating at 200 MHz, chloroform shows a single sharp absorption at 7.3.
(a)How many parts per million downfield from TMS does chloroform absorb?
(b)How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz?
(c)What would be the position of the chloroform absorption inunits when measured on a 360 MHz spectrometer?
Question: Predict the number of carbon resonance lines you would expect in the C- 13 NMR spectra of the following compounds:
(a) Methylcyclopentane
(b) 1- Methylcyclohexane
(c) 1,2- Dimethylbenzene
(d) 2- Methyl-2-butene
(e)
(f)
Carboxylic acids react with alcohols (R'OH) in the presence of an acid catalyst. The reaction product of propanoic acid with methanol has the following spectroscopic properties. Propose a structure.
MS: = 88
IR: 1735
NMR: 1.11 (3 H, triplet, J 5 7 Hz); 2.32 (2 H, quartet, J 5 7 Hz); 3.65 (3 H, singlet) NMR: 9.3, 27.6, 51.4, 174.6
Nitriles (RC≡N) react with Grignard reagents (R'MgBr). The reaction product from 2-methylpropanenitrile with methyl magnesium bromide has the following spectroscopic properties. Propose a structure.
MS:=86
IR: 1715
NMR: 1.05 (6 H, doublet, J 5 7 Hz); 2.12 (3 H, singlet); 2.67 (1 H, septet, J 5 7 Hz) NMR: 18.2, 27.2, 41.6, 211.2
Question: Sketch what you might expect the1H and13C NMR spectra of the following compound to look like (green=Cl):
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