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1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:

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Presentation on theme: "1 H NMR Interpretation Using the NMR Mosaic. Each peak represents a fragment of the molecule Peak carries three critical pieces of information –Integration:"— Presentation transcript:

1 1 H NMR Interpretation Using the NMR Mosaic

2 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

3 Integration RELATIVE number of hydrogens Measure rise of line over peak 2H 2H3H C 3 H 7 Cl

4 Chemical Shifts OH, NH Alkene Adjacent to Oxygen Adjacent to Cl, Br, I Adjacent to double bond Alkane-like Aromatic Aldehyde hydrogen Carboxylic acid hydrogen Functional groups on or next to fragment

5 Chemical Shifts C 3 H 7 Cl Next to Cl Alkane-like

6 Multiplicity (Splitting) NEIGHBOR hydrogens = number of peaks -1

7 Multiplicity (Splitting) 3 peaks (triplet) 2 neighbor H’s (probably CH 2 ) 6 peaks (hextet) 5 H’s (CH 3 & CH 2 ) 3 peaks (triplet) 2 neighbor H’s (CH 2 )

8 Create Molecule: Put pieces together C 3 H 7 Cl Peak is a CH 2 -Next to Cl -Next to CH 2 Peak is a CH 2 -No Funct. Grp. -Next to CH 2 -Next to CH 3 Peak is a CH 3 -No Functional Group -Next to CH 2

9 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

10 Steps for Solving 1 H NMR Spectra 1.Calculate integration for each peak a.#H = peak integration x (total # H’s / total integration) b.Smallest peak is often 1H c.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)

11 Calculate # H’s for each peak C 3 H 7 Cl

12 Calculate # H’s for each peak C 3 H 7 Cl 2H 2H3H

13 Make NMR Mosaic Pieces : C 3 H 7 Cl H | ─C─ | H

14 | ─C─ | H CH 2 Make NMR Mosaic Pieces : C 3 H 7 Cl

15 H | ─C─ | H CH 2 Funct. Grp. Make NMR Mosaic Pieces : C 3 H 7 Cl

16 X- H | ─C─ | H CH 2 Funct. Grp. Make NMR Mosaic Pieces : C 3 H 7 Cl

17 X- H | ─C─ | H CH 2 Funct. Grp. Make NMR Mosaic Pieces : C 3 H 7 Cl H | ─C─ | H

18 X- H | ─C─ | H CH 2 Funct. Grp. Make NMR Mosaic Pieces : C 3 H 7 Cl H | ─C─ | H CH 3

19 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 CH 3 Make NMR Mosaic Pieces : C 3 H 7 Cl

20 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 CH 3 H | H─C─ | H Make NMR Mosaic Pieces : C 3 H 7 Cl

21 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 CH 3 H | H─C─ | H CH 2 Make NMR Mosaic Pieces : C 3 H 7 Cl

22 Fit pieces together Great! Errors. Great! Error.

23 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 CH 3 H | H─C─ | H CH 2 1-chloropropane Make NMR Mosaic Pieces : C 3 H 7 Cl

24 C 6 H 12 O 2

25 H | ─C─ | H Funct. Grp. CH ─ O ─

26 C 6 H 12 O 2 H | H─C─ | H Funct. Grp. H | ─C─ | H Funct. Grp. CH ─ O ─ O || ─ C ─

27 C 6 H 12 O 2 H | H─C─ | H Funct. Grp. H | ─C─ | H Funct. Grp. CH H | ─C─ | CH 3 CH 2 CH 3 ─ O ─ O || ─ C ─

28 C 6 H 12 O 2 H | H─C─ | H Funct. Grp. H | H─C─ | H CH H | ─C─ | H Funct. Grp. CH H | ─C─ | CH 3 CH 2 CH 3 ─ O ─ O || ─ C ─ H | H─C─ | H CH

29 C 6 H 12 O 2 : Isobutyl acetate ─ O ─ O || ─ C ─ H | H─C─ | H Funct. Grp. H | H─C─ | H CH H | ─C─ | H Funct. Grp. CH H | ─C─ | CH 3 CH 2 CH 3 H | H─C─ | H CH Must Watch Chemical Shifts!

30 C 7 H 14 O 2

31 ─ O ─ H | ─C─ | Funct. Grp. CH 3

32 C 7 H 14 O 2 ─ O ─ H | ─C─ | Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. O || ─ C ─

33 C 7 H 14 O 2 ─ O ─ H | ─C─ | Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. O || ─ C ─ H | ─C─ | H CH 2 CH 3

34 C 7 H 14 O 2 ─ O ─ H | ─C─ | Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. O || ─ C ─ H | ─C─ | H CH 2 CH 3 H | H─C─ | H CH (2 of these) H | H─C─ | H CH

35 C 7 H 14 O 2 ─ O ─ H | ─C─ | Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. O || ─ C ─ H | ─C─ | H CH 2 CH 3 H | H─C─ | H CH (2 of these) H | H─C─ | H CH 2 H | H─C─ | H CH

36 C 7 H 14 O 2 : Isopropyl butyrate H | ─C─ | H CH 2 CH 3 H | ─C─ | H CH 2 Funct. Grp. H | H─C─ | H CH H | H─C─ | H CH H | H─C─ | H CH 2 ─ O ─ O || ─ C ─ H | ─C─ | Funct. Grp. CH 3

37 C 6 H 11 O 2 Cl

38 C 6 H 12 O 2 Cl ─ O ─ H | ─C─ | H Funct. Grp. CH 3

39 C 6 H 12 O 2 Cl ─ O ─ H | ─C─ | H Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. X-

40 C 6 H 12 O 2 Cl ─ O ─ H | ─C─ | H Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 Funct. Grp.

41 C 6 H 12 O 2 Cl ─ O ─ H | ─C─ | H Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 Funct. Grp. H | ─C─ | H CH 2

42 C 6 H 12 O 2 Cl ─ O ─ H | ─C─ | H Funct. Grp. CH 3 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 Funct. Grp. H | ─C─ | H CH 2 H | H─C─ | H CH 2

43 C 6 H 12 O 2 Cl: Ethyl 4-chlorobutyrate ─ O ─ O || ─ C ─ H | ─C─ | H Funct. Grp. CH 3 H | H─C─ | H CH 2 H | ─C─ | H CH 2 Funct. Grp. X- H | ─C─ | H CH 2 H | ─C─ | H CH 2 Funct. Grp.

44 NMR Mosaic Simplifies Interpretation of Complex Multiplets Adjoining pieces specify connectivity Interpretation is no longer “impossible”

45 Example: C 4 H 9 Cl

46 X- H | ─C─ | Funct. Grp. CH 3 CH 2

47 Example: C 4 H 9 Cl X- H | ─C─ | Funct. Grp. CH 3 CH 2 H | ─C─ | H Undetermined Splitting

48 Example: C 4 H 9 Cl X- H | ─C─ | Funct. Grp. CH 3 CH 2 H | ─C─ | H Undetermined Splitting H | H─C─ | H CH

49 Example: C 4 H 9 Cl X- H | ─C─ | Funct. Grp. CH 3 CH 2 H | ─C─ | H Undetermined Splitting H | H─C─ | H CH H | H─C─ | H CH 2

50 Example: C 4 H 9 Cl X- H | ─C─ | Funct. Grp. CH 3 CH 2 H | ─C─ | H Undetermined Splitting H | H─C─ | H CH H | H─C─ | H CH 2

51 Example: C 4 H 9 Cl X- H | ─C─ | Funct. Grp. CH 3 CH 2 H | H─C─ | H CH H | H─C─ | H CH 2 H | ─C─ | H CH CH 3 2-chlorobutane

52 NMR Mosaic Helps You Catch Mistakes Mosaic pieces no longer match Focus students on incorrectly interpreted peaks

53 Example: C 3 H 7 Cl

54 H | H─C─ | H CH 2 H | ─C─ | H CH 3 H | ─C─ | H CH 2 Funct. Grp. X- Incorrect Match ↑

55 Example: C 3 H 7 Cl H | H─C─ | H CH 2 H | ─C─ | H CH 2 Funct. Grp. X- Corrected Piece Matches H | ─C─ | H CH 2 CH 3

56 Steps for Solving 1 H NMR Spectra 1. 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.

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