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(More) NMR practice problems. Sources: http://www.chem.ucla.edu/~webspectra/ http:// www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi. Ch14C, Spring 2012 Prof. Dong. Rough 13 C-NMR guidelines. ketone 210 ppm aldehyde 200 (this is a nice even number to remember) carboxylic acid 180

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more nmr practice problems

(More) NMR practice problems

Sources:

http://www.chem.ucla.edu/~webspectra/

http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi

  • Ch14C, Spring 2012
  • Prof. Dong
rough 13 c nmr guidelines
Rough 13C-NMR guidelines
  • ketone 210 ppm
  • aldehyde 200 (this is a nice even number to remember)
  • carboxylic acid 180
  • ester/amide 170
  • C=C 120
  • C≡C 80
  • C-O 60 (note that CHCl3 appears at 77 ppm)
  • C-C 0-30
    • CH4 -2.3
    • Neobutane25.0
  • TMS Si(CH3)4 0 ppm (set as reference)
slide3

For each structure:1. Calculate the number of peaks you would expect on 13C-NMR for each of these structures. 2. Using the molecular formula, calculate the number of DBEs expected and compare it to the actual structure

Answers. Number of equivalent carbons (from left to right): 5, 6, 9, 3, 1, 5

beginner 7 c 14 h 14
Beginner #7, C14H14

Solvent: CHCl3

beginner 10 c 10 h 10 o 2
Beginner #10, C10H10O2

194.452

158.166

148.135

132.603

128.900

128.740

122.796

120.738

111.175

55.4332

Solvent: CHCl3

beginner 12 c 6 h 12 o 2
Beginner #12 C6H12O2

Solvent: CHCl3

beginner 25 c 4 h 8 o
Beginner #25, C4H8O

Solvent: CHCl3

int1 1 c 3 h 4 o
Int1 #1, C3H4O

Solvent: CHCl3

0

200

int1 16 c 6 h 10 o
Int1 #16, C6H10O

Solvent: CHCl3

int1 2 c 8 h 12 o 2
Int1 #2, C8H12O2

2H,sextet

3H,t

2H, t

2H,p

3H, s

1H-NMR

3H,t

2H, t

2H,sextet

2H,p

13C-NMR

Solvent: CHCl3

int2 13 c 10 h 15 n
Int2 #13, C10H15N

Example of a DEPT 13C-NMR spectra (four 13C-NMR spectra)

Solvent: CHCl3

The normal, “standard” 13C-NMR

Up: CH, CH2, CH3

Up: CH

Up: CH and CH3

Down: CH2

int 12 c 7 h 9 no
Int#12, C7H9NO

Solvent: CHCl3

The normal, standard 13C-NMR

Up: CH, CH2, CH3

Up: CH

Up: CH and CH3

Down: CH2

160

50

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