NMR - From the Spectra to the Structure

Problem Formula Problem Formula

number number

1 Cl(CH2)3CN 11 H2N CH3

2 H3C CH CH CHO Cl

O
COOH
3 H3C C COOCH3 12 O
COOH

4 H3C CH2 CH CH2OH 13 C CH2Br

NH2 O

O2N O
5 14 H2N NH C CH3
N Cl

6 15 H3CO CH2 OH
N NH2

CN
7 HO F 16
H3C

8 17 H3CO NH2
H3CO N Cl
H3CO

O
H3C C CH
3
9 HO 18

NH2

NO2

10 HOOC 19 CH CH CHO

NO2
 NMR - From the Spectra to the Structure
Problem Formula Problem Formula
number number
H3C
20 H3CO CH2OH 28 C CH CH2CH2 C CH CH2
H3C CH3 O
H3CO C
O CH3

H3C CH3
H3C COOH
CH CH C CH3
21 29 O
H3C
CH3

CH3
(CH3)2N N(CH3)2
O
22 30

C
H3C CH2

H3C CH3 C2H5OOC CH COOC2H5

O O CH2
23 31

H3C CH3

CHO
H3C OH OH CH3
24 CH O C CH CH C O CH 32
H3C O O CH3

CHO
OH H3C OH
25 33
CH3 CH3 CH3

H3C CH3 OH
26 34 C CH CH2CH2 C CH CH2 C CH CH2
H3C CH3
C2H5OOC COOC2H5

O
27 C C COOC2H5 35 P C C C4H9
NC OH
 Problems 36-50 (2nd Edition)

Problem
number Formula and data

36
Cl
5
Cl 4 O 3 H
6
C 2 1
Cl O P(OCH2CH3)2
Cl
O

C atom  [ppm] J (31P-13C) [Hz] J (13C-1H) [Hz]

1
1 16.77 5.2 JCH = 127.5 ; 2JCH = 2.5
1
2 64.98 6.8 JCH = 149.9 ; 2JCH = 4.3
1
3 107.75 196.7 JCH = 176.6
3
4 144.33 2.3 JCH = 2.3
5 113.40 - -
6 126.10 - -

37
T1= 4.7 sec
110.3
102.6 T1= 3.4 sec
Cl O
CH2
Cl O

124.5 147.3 T1= 61.8 sec

T1= 70.4 sec

38a 38b
O O
PB(Oi-C3H7)2 PB(Oi-C3H7)2
T1= 6.5sec T1= 4.2 sec

PA(C6H5)2 PA(C6H5)2
T1= 4.7 sec S T1= 8.5 sec

39 40
S

NH Cl Cl
N S
H N OH
Problem
number Formula and data

41 protons of the CH2 group not equivalent :

( AB system)
CH3O C CHAHB CHX C OCH3
O OH O
(HA) = 2.78 ppm 2J(HAHB) = 16.5 Hz ; 3J(HAHX) = 4.4 Hz
(HB) = 2.71 ppm 2J(HAHB) = 16.5 Hz ; 3J(HBHX) = 6.2 Hz
(HX) = 4.44 ppm 3J(HAHX) = 4.4 Hz ; 3J(HBHX) = 6.2 Hz

42 protons of the CH2 group not equivalent :

( AB system)
O O
CH3O C CHAHB CHX C OCH3
NH3 Cl 2
J(H = 18.3 Hz ; 3J(HAHX) = 5.1 Hz ;
AHB)
3
J(HBHX) = 5.1 Hz ; 3J(HX-NH) = 5.3 Hz

43
O
4

5
CH
3

2
6

N OCH3
1

(CHO) = 10.30 ppm d ( 5JHH = 0.83Hz )

(H4) = 8.08 ppm dd ( 3JHH = 7.3 Hz ; 4JHH = 2.08 Hz )
(H5) = 6.98 ppm ddd ( 3JHH = 7.3 Hz ; 3JHH = 4.83 Hz ; 5JHH = 0.83Hz )
(H6) = 8.36 ppm dd ( 3JHH = 7.3 Hz ; 4JHH = 2.08 Hz )
(OCH3) = 4.08 ppm s

44
4
F3C CF3
5 3

6 2
1

Br

characteristic coupling constants :

(CF3) = 122.6 ppm q ( 1J(FC) = 273.0 Hz )
(C3) = 133.5 ppm q ( 2J(FC) = 34.2 Hz )
Problem
number Formula and data

45
Br

46

H3C

CH2 PBr2

H3C
characteristic coupling constants :
2
J(PH) = 16.8 Hz ; 1J(PC) = 49.6 Hz

47

F
Ti
F
3 2
J(FH) = 1.7 Hz ; J(FC) = 2.5 Hz

48

Br

Br

49

50

S O
CH P
S