EXAMEN RMN 1H

EXAMEN RMN
1H
HUMBERTO GÓMEZ RUIZ
2013
EJERCICIO # 1
C4H10O
11.5
3
11.0
0.88, 1.89
10.5
10.0
9.5
1.11, 1.69
9.0
3
8.5
8.0
1.09, 1.36
7.5
7.0
6.5
6.0
5.5
2
5.0
4.5
0.90, 0.78
0.85, 0.65
4.0
3.5
3.0
2.5
1
1
2.0
1.5
3.59, 0.13
1.0
3.64, 0.04
0.5
0.0
1.39, 0.24
1.37, 0.23
1.42, 0.19
2.52, 0.13
10
9
8
7
6
5
4
3
2
1
0
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
Group
1
2
3<''>
3<'>
4
5
nH
1
1
1
1
3
3
Error
1.44
-----------
Shift
2.52
3.59
1.41
1.38
0.88
1.10
0.88, 1.89
1.11, 1.69
1.09, 1.36
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
J
J
3
J
4
J
3
J
2
J
3
J
2
J
3
J
4
J
4
J
2
J
2.0
1.5
1.0
0.5
0.0
Grp.1
2
2
2
3<''>
3<'>
3<'>
4
5
5
5
5
3
3.60, 0.12
3.62, 0.12
Grp.2
3<''>
3<'>
4
4
3<''>
4
4
2
3<''>
3<'>
5
Value
2.93
5.43
-0.07
7.09
-13.00
7.63
3.58
7.07
-0.22
-0.22
13.10
3.59, 0.13
3.59, 0.12
3.58, 0.12
3.56, 0.12
Error
----0.10
------9.50
--0.10
0.10
--1.39, 0.24
1.41, 0.17
1.42, 0.19
2.52, 0.13
1.44, 0.07
1.46, 0.01
1.49, 0.0034
3.56, 0.04
3.5
3.0
2.5
2.0
1.5
1.0
EJERCICIO # 2
C4H8O
9.5
9.0
8.5
3
2.04, 2.96
8.0
7.5
7.0
3
6.5
6.0
5.5
0.99, 1.77
5.0
4.5
4.0
2
3.5
3.0
1.01, 0.91
0.96, 0.85
2.5
2.45, 0.67
2.48, 0.65
2.0
1.5
2.43, 0.23
2.50, 0.21
1.0
0.5
0.0
10
9
8
7
6
5
4
3
2
1
0
9.5
9.0
8.5
3
2.04, 2.96
8.0
7.5
3
7.0
6.5
6.0
5.5
0.99, 1.77
5.0
4.5
4.0
3.5
2
3.0
1.01, 0.91
2.5
2.0
2.45, 0.67
2.48, 0.65
1.5
1.0
2.43, 0.23
2.50, 0.21
0.5
0.0
2.60
2.50
2.40
2.30
2.20
2.10
2.00
1.90
1.80
1.70
1.60
1.50
1.40
1.30
1.20
1.10
1.00
0.90
EJERCICIO # 3
C9H10O
11.5
11.0
10.5
10.0
9.5
Group
2
3
5
6
7
10
nH
1
1
1
1
3
3
Shift
7.16
7.75
7.75
7.16
2.43
2.52
Error
--------0.05
---
2.52, 3.82
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
J
J
4
J
5
J
5
J
4
J
3
J
5
J
4
J
5
J
4
J
2
J
2
J
3
Grp.1
2
2
3
5
5
5
5
6
6
6
7
10
Grp.2
3
7
7
2
3
6
7
2
3
7
7
10
Value
8.16
-0.71
0.34
0.20
1.80
8.16
0.34
2.21
0.20
-0.71
2.88
2.88
Error
--------------------8.40
8.40
6
2.44, 1.57
4.5
4.0
3.5
2
2
3.0
2.5
7.74, 0.57
7.76, 0.52
2.0
7.17, 0.42
7.15, 0.39
1.5
1.0
0.5
0.0
10
9
8
7
6
5
4
3
2
1
0
11.5
11.0
2.52, 3.82
10.5
10.0
9.5
6
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
2
5.0
2.44, 1.57
4.5
4.0
3.5
2
3.0
2.5
2.0
7.76, 0.52
1.5
7.74, 0.57
7.17, 0.42
7.15, 0.39
1.0
0.5
0.0
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
EJERCICIO # 4
C9H12O
C9H12O
5
3
1
triplete
1
2
quinteto
triplete
EJERCICIO # 5
C8H12O4
1730
400 MHz
C8H12O4
3
1
2
cuarteto
triplete
EJERCICIO # 5
C7H12O4
1735
400 MHz
3
C7H12O4
1
2
cuarteto
triplete
EJERCICIO # 6
C8H7N
2229
400 MHz
C8H7N
4
3
TABLAS DE CORRELACIÓN
INFRAROJO BASICO
3000
VALORES BASE
OH
NH
3600
3400
CH
3000
C N
C C
2250
2150
C=O
1715
C=C
1650
C-O
1100
3300
3100
C-H
=C-H
EXPANDIDO CH
2900 2850
2750
-C-H
-CHO
CH2 y CH3 bend. :
1800
1735
1465 y 1365
1725
1715
1690
ácido
aldehido
Cloruro ester
de ácido
1710
amida
ketone
anhidrido: 1810 y 1760
EXPANDIDO C=O
benceno C=C : entre 1400 y 1600
recuerde que los efectos de H-puente, conjugación y tamaño del anillo.
Tabla de correlación RMN
-OH -NH
CAMPO BAJO
DESPROTEGIDO
CAMPO ALTO
PROTEGIDO
CHCl3 , H
TMS
12
RCOOH
11
10
9
RCHO
8
7
6
H
C=C
5
4
CH2F
CH2Cl
CH2Br
CH2I
CH2O
CH2NO2
3
2
1
0
δ (ppm)
CH2Ar
C-CH-C
CH2NR2
C
CH2S
C-CH2-C
C C-H
C=C-CH2 C-CH3
CH2-CO
Los intervalos se pueden definir para diferentes tipos de protones.
Esta tabla es general, es más clara la siguiente diapositiva.
DESPLAZAMIENTOS QUÍMICOS (APROX,) (ppm) PARA DIFERENTES PROTONES
R-CH3
R-CH2-R
R3CH
0.7 - 1.3
1.2 - 1.4
1.4 - 1.7
R-C=C-C-H
O
1.6 - 2.6
R-C-C-H
O
2.1 - 2.4
RO-C-C-H
O
2.1 - 2.5
HO-C-C-H
2.1 - 2.5
N C-C-H
2.1 - 3.0
R-C C-C-H
2.1 - 3.0
C-H
R-C C-H
R-N-C-H
2.2 - 2.9
R-S-C-H
2.0 - 3.0
I-C-H
2.0 - 4.0
Br-C-H
2.7 - 4.1
Cl-C-H
3.1 - 4.1
RO-C-H
3.2 - 3.8
HO-C-H
3.2 - 3.8
O
R-C-O-C-H
3.5 - 4.8
O2N-C-H
4.1 - 4.3
F-C-H
4.2 - 4.8
R-C=C-H
4.5 - 6.5
H
6.5 - 8.0
O
R-C-N-H
5.0 - 9.0
O
R-C-H
9.0 - 10.0
O
R-C-O-H
11.0 - 12.0
2.3 - 2.7
R-N-H 0.5 - 4.0
Ar-N-H 3.0 - 5.0
1.7 - 2.7
R-O-H 0.5 - 5.0
Ar-O-H 4.0 - 7.0 1.0 - 4.0
R-S-H
10
ALQUENOS
R
Monosustituidos
Disustituidos
cis-1,2-
trans-1,2-
Trisustituidos
Tetrasustituidos
12
13
C C
H
H
R
R
s
15 µ
s
s
C C
H
H
H
R
C C
s
H
H
C C
R
H
R
R
s
m
C C
R
H
R
R
C C
R
14
H
R
R
1,1-
11
R
=C-H BENDING FUERA DEL PLANO
1000
900
800
700 cm-1
BENCENOS
10
11
12
13
14
Monosustituidos
s
15 µ
s
Disustituidos
s
orto
m
meta
s
para
s
ANILLO H’s
fdeP
Trisustituidos
m
1,2,4
s
1,2,3
s
1,3,5
Bandas de combinación
s
m
s
1000
900
m
800
700 cm-1