1

1. For CNH#O#N# IHD = 2N+2 - (#hydrogens+#halogens) + (#Ns)! ! ! ! ! 2 !!

You Should Know:!

75! 50!

C O C C C CC

0!50!100!150!200!

40! -5!

sp3!90! 70!sp!150! 105!

sp2!

150! 120!

aromatic!

210! 160!

carbonyl!

60! 18!C N

C O4. Typical 13C chemical shifts!

2. How to identify symmetry and use it.!!3. Proton Inventory. Identify if any protons are attached to non-carbon atoms by!Summing the number of C-attached protons and comparing to molecular formula !

5. multiplicities!

Carbon NMR essentials

16.315.8

13.425.2

13.9 34.7

22.8

14.1 32.2

23.1

14.132.6

23.2 29.7

32.6

23.2 29.9

propane butane pentane hexane

heptane

14.2

octane

32.6

23.2 30.0

14.2

nonane

30.3

32.6

23.2 31.1

decane

30.514.225.4

24.5

isobutane

31.1

32.0

isopentane

11.7

22.2

28.0

32.0

isohexane

20.9

22.714.328.1

31.7

neopentane

36.9

30.6

2,2-dimethylbutane

29.1

8.9

3-methylpentane29.5

11.8

11.536.9

2,3-dimethylbutane

19.534.3

2,2,3-trimethylbutane

27.433.138.3

16.1

H3C CH35.7

ethane-2.3 methaneCH4

base values

etc...

10.1

25.2

65.046.7

27.3

64.9

27.3

32.0 69.5

32.0 32.0

OHOH OH OH

Alcohols

19.2

30.9

72.6

19.2

OH

67.4

82.8 17.4

29.9

21.2

12.973.7

76.9

19.6

12.1

1.7

21.6

79.9

12.0

14.4

Alkyne Chemical Shifts

CHO =O

H

key:

15.246.6 35.9

NH

51.7 42.8

62.313.3

21.221.2

N3.06

3.06

N

Amine Chemical Shifts

CO2H =O

OH CO2Me =

O

OMe

key:29.7

174.610.0 34.1

15.0NH

O

23.0 171.025.9

NH

O

20.5 169.532.9

37.9

N

O

129.4

133.0

112.6

132.2118.6

C N 19.6

119.318.813.0

C N