Question

Write a structure consistent with the molecular formula and H-NMR spectrum. Symmetry is important for many of them to reduce the number of NMR peaks expected. Show all necessary workings and explanations. 12. CaHO (One hydrogen, broad singlet, not shown. 9. C4HO2 (singlet integrates to 3 hydrogens) 10. CsHgN (ratio peak areas: 2

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Answer #1

9.

the quartet and triplet at around 4 and 1.5 ppm is due to ethyl group attached to oxygen

singlet at 2 ppm is due to methyl group attached to carbonyl group

therefore the structure of the compound is ethyl acetate

ethyl acetate

12.

the multiplet at 3.8 ppm is for CH proton

the doublet at 1.1 ppm is for methyl proton

the broad singlet is for hydroxy group (-OH)

но. propan-2-ol

10.

the doublet at around 2.6 ppm is for methylene group attached to CN

the multiplet at around 1.7 ppm is for CH proton attached to methyl and methylene group

the doublet at around 0.9 ppm is for methyl group attached to CH

therefore the structure of the compound is

NC 3-methylbutanenitrile

13.

the quartet and triplet at 2.5 and 1 ppm is for three ethyl group attached to nitrogen

therefore the structure of the compound is

N triethylamine

11.

the triplet at 3.5 ppm is for methylene group attached to oxygen

the multiplet at 1.5 ppm is for methylene group attached to methylene and methyl group

the triplet at 1 ppm is for methyl group attached methylene group

therefore the structure of the compound is n-propanol

CH3-CH2-CH2-OH

14.

the singlet 2.8 ppm is due to methyl group attached to nitrogen

the singlet at 2 ppm is due to methyl group attached to carbonyl group

the singlet at 7.5 ppm is due to proton attached to nitrogen

therefore the structure of the compound is

NH N-methylacetanmide

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