Chem 30CL-Lecture 5c

Chem 30CL-Lecture 5c - 150 140 130 120 110 100 90 80 70 60...

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Click to edit Master subtitle style 8/6/11 NMR spectroscopy of Epoxides Lecture 5c
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8/6/11 1H-NMR spectroscopy is used to determine the structure of the epoxide based on characteristic splitting patterns in aromatic range and epoxide range When analyzing the spectrum, it will become more difficult if the submitted sample is a mixture of compounds i.e. epoxide, aldehyde, solvents, water, etc The carbon spectrum will show a triplet at δ =77 ppm due to the presence of CDCl3. The proton spectrum might show a singlet at δ =7.26 ppm due to the presence of CDCl3 if the concentration of the epoxide is very low. Introduction
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8/6/11 1H-NMR spectrum 4-Methylstyrene oxide 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 O H 1 H 3 H 2 H 3 C 3.5 3.0 2.5 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 H1, dd H2, dd H3, dd 4 1 1 1 3
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8/6/11
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Unformatted text preview: 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 5 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 (10) (2) (3) (Sol.) (Sol.) (Sol.) (5;9) (8;6) (4) 13C-NMR spectrum Seven signals total Epoxide carbons at ~ 50-60 ppm 4-Methylstyrene oxide 8 7 6 5 4 9 3 2 O 1 H 3a H 2a H 2b C H 3 10 CDCl 3 8/6/11 9 8 7 6 5 4 3 2 1 1 2 3 4 5 6 7 8 9 10 11 1H-NMR spectrum 4-Methylbenzacetaldehyde O H H H 3 C H CH2, s CHO, s 8/6/11 200 150 100 50 5 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 105 110 115 120 (10) (7) (Sol.) (Sol.) (Sol.) (5;3) (1) (2;6) (4) (8) 13C-NMR spectrum Aldehyde: ~200 ppm Methylene: 45-50 ppm 4-Methylbenzacetaldehyde 5 4 3 2 1 6 7 8 O 9 H 7a H 8a C H 3 10 H 7b CHO CH 2 CDCl 3...
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This note was uploaded on 08/06/2011 for the course CHEM 30CL taught by Professor Bacher during the Fall '08 term at UCLA.

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Chem 30CL-Lecture 5c - 150 140 130 120 110 100 90 80 70 60...

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