1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak...
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Transcript of 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak...
![Page 1: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/1.jpg)
1H NMR Interpretation Using the NMR Mosaic
![Page 2: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/2.jpg)
Each peak represents a fragment of the molecule
Peak carries three critical pieces of information– Integration: how many hydrogens on that
fragment– Chemical shift: functional group on or next to
the fragment– Multiplicity: how many next-door hydrogens
![Page 3: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/3.jpg)
Integration• RELATIVE number of hydrogens• Measure rise of line over peak
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
2H 2H 3H
C3H7Cl
![Page 4: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/4.jpg)
12 11 10 9 8 7 6 5 4 3 2 1
3 0 0 M H z ¹H N M RIn C D C l3
A L L R IG H T S R E S E R V E D© S igma-A ld rich C o .
Chemical Shifts
OH, NH
Alkene
Adjacent to Oxygen
Adjacent to Cl, Br, I
Adjacent to double bond
Alkane-likeAromatic
Aldehyde hydrogen
Carboxylic acid hydrogen
•Functional groups on or next to fragment
![Page 5: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/5.jpg)
Chemical Shifts
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
C3H7Cl
Next to ClAlkane-like
![Page 6: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/6.jpg)
Multiplicity (Splitting)
• NEIGHBOR hydrogens = number of peaks -1
![Page 7: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/7.jpg)
Multiplicity (Splitting)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
3 peaks (triplet) 2 neighbor H’s(probably CH2)
6 peaks (hextet)5 H’s(CH3 & CH2)
3 peaks (triplet) 2 neighbor H’s(CH2)
![Page 8: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/8.jpg)
Create Molecule: Put pieces together
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
C3H7Cl
Peak is a CH2 -Next to Cl -Next to CH2
Peak is a CH2 -No Funct. Grp. -Next to CH2
-Next to CH3
Peak is a CH3 -No Functional Group -Next to CH2
![Page 9: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/9.jpg)
The NMR Mosaic can help
• Reminds you to use integration AND chemical shift AND multiplicity
• Helps you visualize how the pieces fit together
• Helps you recognize mistakes in interpretation
• Helps you interpret complex splitting
![Page 10: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/10.jpg)
Steps for Solving 1H NMR Spectra1. Calculate integration for each peak
a. #H = peak integration x (total # H’s / total integration)b. Smallest peak is often 1Hc. Peaks ~1 are often 3H (methyl)
2. Determine number of adjacent hydrogens from splitting- Number of peaks = n+1, where n = number of adjacent
hydrogens- Attach appropriate static cling(s)
3. Determine presence of functional group(s)- Attach functional group static cling(s)- Choose functional group Mosaic piece(s)
![Page 11: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/11.jpg)
Calculate # H’s for each peak
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
C3H7Cl
![Page 12: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/12.jpg)
Calculate # H’s for each peak
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
C3H7Cl
2H 2H 3H
![Page 13: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/13.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
Make NMR Mosaic Pieces: C3H7Cl
H | ─C─ | H
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2
Make NMR Mosaic Pieces: C3H7Cl
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2 Func
t. G
rp.
Make NMR Mosaic Pieces: C3H7Cl
![Page 16: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/16.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
Make NMR Mosaic Pieces: C3H7Cl
![Page 17: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/17.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
Make NMR Mosaic Pieces: C3H7Cl
H | ─C─ | H
![Page 18: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/18.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
Make NMR Mosaic Pieces: C3H7Cl
H | ─C─ | H
CH3
![Page 19: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/19.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2
CH3
Make NMR Mosaic Pieces: C3H7Cl
![Page 20: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/20.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2
CH3
H |H─C─ | H
Make NMR Mosaic Pieces: C3H7Cl
![Page 21: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/21.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2
CH3
H |H─C─ | H
CH2
Make NMR Mosaic Pieces: C3H7Cl
![Page 22: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/22.jpg)
Fit pieces togetherH|
─C─|
HCH2 Fu
nct.
Grp
.
AlkeneH
CH2
CH
H|
─C─|
H
CH2
CH
H|
─C─|
HCH2 Fu
nct.
Grp
.
H|
─C─|
HCH2 Fu
nct.
Grp
.
AlkeneH
CH2
CH
AlkeneH
AlkeneH
CH2
CH
H|
─C─|
H
CH2
CH
H|
─C─|
H
H|
─C─|
H
CH2
CH
H|
H─C─|
H
CH2H|
─C─|
HCH3
CHH|
─C─|
H
CH2
CH
H|
H─C─|
H
CH2H|
H─C─|
H
H|
H─C─|
H
CH2H|
─C─|
HCH3
CHH|
─C─|
HCH3
CHH|
─C─|
H
CH2
CH
H|
─C─|
H
H|
─C─|
H
CH2
CH
H|
─C─|
HCH2 Fu
nct.
Grp
.H|
─C─|
HCH2 Fu
nct.
Grp
.
─ O ── O ─
H|
─C─|
HCH3Funct. G
rp. H|
─C─|
HCH3Funct. G
rp.
H|
─C─|
HCH2 Fu
nct.
Grp
.H|
─C─|
HCH2 Fu
nct.
Grp
.
H|
─C─|
HCH3Funct. G
rp. H|
─C─|
HCH3Funct. G
rp.
Great! Errors.
Great! Error.
![Page 23: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/23.jpg)
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2
CH3
H |H─C─ | H
CH2
1-chloropropane
Make NMR Mosaic Pieces: C3H7Cl
![Page 24: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/24.jpg)
C6H12O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
![Page 25: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/25.jpg)
C6H12O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
Funct. Grp.
CH
─ O ─
![Page 26: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/26.jpg)
C6H12O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H |H─C─ | H
Func
t. G
rp.
H | ─C─ | H
Funct. Grp.
CH
─ O ─
O || ─ C ─
![Page 27: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/27.jpg)
C6H12O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H |H─C─ | H
Func
t. G
rp.
H | ─C─ | H
Funct. Grp.
CH
H | ─C─ |
CH
3
CH2
CH3
─ O ─
O || ─ C ─
![Page 28: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/28.jpg)
C6H12O2
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1.00
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H |H─C─ | H
Func
t. G
rp. H
|H─C─ | H
CH
H | ─C─ | H
Funct. Grp.
CH
H | ─C─ |
CH
3
CH2
CH3
─ O ─
O || ─ C ─
H |H─C─ | H
CH
![Page 29: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/29.jpg)
C6H12O2: Isobutyl acetate
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
O || ─ C ─
H |H─C─ | H
Func
t. G
rp.
H
|
H─
C─
|
H
CH
H | ─C─ | H
Funct. Grp.
CH H | ─C─ |
CH
3
CH2
CH3
H |H─C─ | H
CH
Must Watch Chemical Shifts!
![Page 30: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/30.jpg)
C7H14O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
![Page 31: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/31.jpg)
C7H14O2
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ |
Func
t. G
rp.
CH
3CH3
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C7H14O2
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1.00
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ |
Func
t. G
rp.
CH
3CH3
H | ─C─ | H
CH2 Func
t. G
rp.
O || ─ C ─
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C7H14O2
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1.00
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300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ |
Func
t. G
rp.
CH
3CH3
H | ─C─ | H
CH2 Func
t. G
rp.
O || ─ C ─
H | ─C─ | H
CH2
CH3
![Page 34: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/34.jpg)
C7H14O2
0.00
0.25
0.50
0.75
1.00
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ |
Func
t. G
rp.
CH
3CH3
H | ─C─ | H
CH2 Func
t. G
rp.
O || ─ C ─
H | ─C─ | H
CH2
CH3
H |H─C─ | H
CH
(2 of these)
H |H─C─ | H
CH
![Page 35: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/35.jpg)
C7H14O2
0.00
0.25
0.50
0.75
1.00
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ |
Func
t. G
rp.
CH
3CH3
H | ─C─ | H
CH2 Func
t. G
rp.
O || ─ C ─
H | ─C─ | H
CH2
CH3
H |H─C─ | H
CH
(2 of these)
H |H─C─ | H
CH2
H |H─C─ | H
CH
![Page 36: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/36.jpg)
C7H14O2: Isopropyl butyrate
0.00
0.25
0.50
0.75
1.00
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H | ─C─ | H
CH2
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
H |H─C─ | H
CH
H |H
─C
─ | H
CH
H |H─C─ | H
CH2
─ O ─
O || ─ C ─
H | ─C─ |
Funct. Grp.
CH
3 CH3
![Page 37: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/37.jpg)
C6H11O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
![Page 38: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/38.jpg)
C6H12O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ | H
Funct. Grp.
CH3
![Page 39: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/39.jpg)
C6H12O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ | H
Funct. Grp.
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
X-
![Page 40: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/40.jpg)
C6H12O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ | H
Funct. Grp.
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
![Page 41: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/41.jpg)
C6H12O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ | H
Funct. Grp.
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
H | ─C─ | H
CH2
CH2
![Page 42: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/42.jpg)
C6H12O2Cl
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
H | ─C─ | H
Funct. Grp.
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2 Func
t. G
rp.
H | ─C─ | H
CH2
CH2
H |H─C─ | H
CH2
![Page 43: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/43.jpg)
C6H12O2Cl: Ethyl 4-chlorobutyrate
0.00
0.25
0.50
0.75
1.00
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
─ O ─
O || ─ C ─ H
| ─C─ | H
Func
t. G
rp.
CH3
H |H─C─ | H
CH2
H | ─C─ | H
CH2 Func
t. G
rp.
X-
H | ─C─ | H
CH2
CH2
H | ─C─ | H
CH2Funct. Grp.
![Page 44: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/44.jpg)
NMR Mosaic Simplifies Interpretation of Complex
Multiplets
• Adjoining pieces specify connectivity
• Interpretation is no longer “impossible”
![Page 45: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/45.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
![Page 46: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/46.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X- H | ─C─ |
Func
t. G
rp.
CH
3CH2
![Page 47: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/47.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X- H | ─C─ |
Func
t. G
rp.
CH
3CH2
H | ─C─ | H
Undetermined
Splitting
![Page 48: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/48.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X- H | ─C─ |
Func
t. G
rp.
CH
3CH2
H | ─C─ | H
Undetermined
Splitting
H |H─C─ | H
CH
![Page 49: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/49.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X- H | ─C─ |
Func
t. G
rp.
CH
3CH2
H | ─C─ | H
Undetermined
Splitting
H |H─C─ | H
CH
H |H─C─ | H
CH2
![Page 50: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/50.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X-
H | ─C─ |
Func
t. G
rp.
CH
3CH2
H | ─C─ | H
Undetermined
Splitting
H
|
H─
C─
|
H
CH
H |H─C─ | H
CH2
![Page 51: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/51.jpg)
Example: C4H9Cl
0.00
0.25
0.50
0.75
1.00
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
X-
H | ─C─ |
Func
t. G
rp.
CH
3CH2
H
|
H─
C─
|
H
CH
H |H─C─ | H
CH2 H | ─C─ | H
CH
CH3
2-chlorobutane
![Page 52: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/52.jpg)
NMR Mosaic Helps You Catch Mistakes
• Mosaic pieces no longer match
• Focus students on incorrectly interpreted peaks
![Page 53: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/53.jpg)
Example: C3H7Cl
-0.1
0.0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
3.5 3.0 2.5 2.0 1.5 1.0
300 MHz ¹H NMRIn CDCl3
ALL RIGH TS RESERVED© S igm a-A ldrich Co.
H|
H─C─|H
CH2H|
H─C─|H
H|
H─C─|H
CH2H|
─C─|H
CH3
CH3
H|
─C─|H
CH3
CH3
H|
─C─|H
CH2 Func
t. G
rp.H
|─C─
|H
CH2 Func
t. G
rp.H
|─C─
|H
CH2 Func
t. G
rp.H
|─C─
|H
CH2 Func
t. G
rp.
Incorrect piece as an example
C3H7Cl
X-
![Page 54: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/54.jpg)
Example: C3H7Cl
-0.1
0.0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
3.5 3.0 2.5 2.0 1.5 1.0
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H |H─C─ | H
CH2 H | ─C─ | H
CH3
CH3
H | ─C─ | H
CH2 Func
t. G
rp.
X-Incorrect Match ↑
![Page 55: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/55.jpg)
Example: C3H7Cl
-0.1
0.0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
3.5 3.0 2.5 2.0 1.5 1.0
300 MHz ¹H NMRIn CDCl3
ALL RIGHTS RESERVED© Sigma-Aldrich Co.
H |H─C─ | H
CH2 H | ─C─ | H
CH2 Func
t. G
rp.
X-Corrected Piece
Matches
H | ─C─ | H
CH2
CH3
![Page 56: 1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:](https://reader034.fdocuments.net/reader034/viewer/2022042723/5a4d1acd7f8b9ab05997022e/html5/thumbnails/56.jpg)
Steps for Solving 1H NMR Spectra1. Calculate integration for each peak
2. For each peak:•Choose correct base Mosaic piece based on integration
- Determine number of adjacent hydrogens from splitting and add static cling tab(s) to base piece
- Determine presence of functional group(s) - Add functional group static cling(s) - Choose appropriate functional group Mosaic piece(s)
3. Put Mosaic pieces together, making sure all colors match and all functional group chemical shifts match.