EXAMEN RMN 1H

HUMBERTO GÓMEZ RUIZ 2013

EJERCICIO # 1

C4H10O

10 9 8 7 6 5 4 3 2 1 00.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

10.0

10.5

11.0

11.5

0.85, 0.65

0.88, 1.89

0.90, 0.78

1.09, 1.36

1.11, 1.69

1.37, 0.231.39, 0.24

1.42, 0.192.52, 0.133.59, 0.13

3.64, 0.04

1

2

1

3

3

3.5 3.0 2.5 2.0 1.5 1.00.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

10.0

10.5

11.0

11.5

0.88, 1.89

1.09, 1.36

1.11, 1.69

1.39, 0.241.41, 0.17

1.42, 0.19

1.44, 0.071.46, 0.01

1.49, 0.0034

2.52, 0.13

3.56, 0.04

3.56, 0.123.58, 0.12

3.59, 0.123.59, 0.13

3.60, 0.123.62, 0.12

Group nH Shift Error1 1 2.52 1.442 1 3.59 ---

3<''> 1 1.41 ---3<'> 1 1.38 ---

4 3 0.88 ---5 3 1.10 ---

J Grp.1 Grp.2 Value Error3J 2 3<''> 2.93 ---3J 2 3<'> 5.43 ---4J 2 4 -0.07 0.103J 3<''> 4 7.09 ---2J 3<'> 3<''> -13.00 ---3J 3<'> 4 7.63 ---2J 4 4 3.58 9.503J 5 2 7.07 ---4J 5 3<''> -0.22 0.104J 5 3<'> -0.22 0.102J 5 5 13.10 ---

EJERCICIO # 2

C4H8O

10 9 8 7 6 5 4 3 2 1 00.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

0.96, 0.85

0.99, 1.77

1.01, 0.91

2.04, 2.96

2.43, 0.23

2.45, 0.672.48, 0.65

2.50, 0.21

2

3

3

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 0.900.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

0.99, 1.77

1.01, 0.91

2.04, 2.96

2.43, 0.23

2.45, 0.672.48, 0.65

2.50, 0.21

3

3

2

EJERCICIO # 3

C9H10O

10 9 8 7 6 5 4 3 2 1 00.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

10.0

10.5

11.0

11.5

2.44, 1.57

2.52, 3.82

7.15, 0.397.17, 0.42

7.74, 0.577.76, 0.52

Group nH Shift Error2 1 7.16 ---3 1 7.75 ---5 1 7.75 ---6 1 7.16 ---7 3 2.43 0.0510 3 2.52 ---

J Grp.1 Grp.2 Value Error3J 2 3 8.16 ---4J 2 7 -0.71 ---5J 3 7 0.34 ---5J 5 2 0.20 ---4J 5 3 1.80 ---3J 5 6 8.16 ---5J 5 7 0.34 ---4J 6 2 2.21 ---5J 6 3 0.20 ---4J 6 7 -0.71 ---2J 7 7 2.88 8.402J 10 10 2.88 8.40

2 2

6

8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.00.0

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

9.5

10.0

10.5

11.0

11.5

2.44, 1.57

2.52, 3.82

7.15, 0.397.17, 0.42

7.74, 0.577.76, 0.52

2

2

6

EJERCICIO # 4

C9H12O

C9H12O

5

1 1 2

3

triplete quinteto triplete

EJERCICIO # 5

C8H12O4

1730

C8H12O4

cuarteto triplete

2

3

1

400 MHz

EJERCICIO # 5

C7H12O4

1735

cuarteto triplete

C7H12O4

400 MHz

2 1

3

EJERCICIO # 6

C8H7N

2229

400 MHz

C8H7N

4

3

TABLAS DE CORRELACIÓN

ácido

INFRAROJO BASICO

OH 3600 NH 3400 CH 3000 C N 2250 C C 2150 C=O 1715 C=C 1650 C-O 1100

3300 3100 2900 2850 2750

3000

1800 1735 1725 1715 1710 1690

=C-H -C-H -CHO

C-H

ketone ester Cloruro de ácido

aldehido amida

anhidrido: 1810 y 1760

CH2 y CH3 bend. : 1465 y 1365

VALORES BASE

recuerde que los efectos de H-puente, conjugación y tamaño del anillo.

benceno C=C : entre 1400 y 1600

EXPANDIDO CH

EXPANDIDO C=O

Tabla de correlación RMN

12 11 10 9 8 7 6 5 4 3 2 1 0

-OH -NH

CH2F CH2Cl CH2Br CH2I CH2O CH2NO2

CH2Ar CH2NR2 CH2S C C-H C=C-CH2 CH2-C-

O

C-CH-C

C

C-CH2-C C-CH3

RCOOH RCHO C=C

H

TMS

HCHCl3 ,

δ (ppm)

CAMPO BAJO CAMPO ALTO

DESPROTEGIDO PROTEGIDO

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 0.7 - 1.3

R-C=C-C-H 1.6 - 2.6

R-C-C-H 2.1 - 2.4

O

O

RO-C-C-H 2.1 - 2.5 O

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 2.3 - 2.7

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

R-C-O-C-H 3.5 - 4.8

O

R-C=C-H

H

6.5 - 8.0

R-C-H

O

9.0 - 10.0

R-C-O-H

O

11.0 - 12.0

O2N-C-H 4.1 - 4.3

F-C-H 4.2 - 4.8

R3CH 1.4 - 1.7 R-CH2-R 1.2 - 1.4 4.5 - 6.5

R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H

R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0

R-C-N-H

O

5.0 - 9.0

1.0 - 4.0 R-C C-H 1.7 - 2.7

Monosustituidos

cis-1,2-

trans-1,2-

1,1-

Trisustituidos

Tetrasustituidos

C CH

R H

H

C CH

R R

H

C CR

H R

H

C CR

R R

R

C CR

R R

H

C CR

R H

H

Disustituidos

10 11 12 13 14 15

1000 900 800 700 cm-1

s s

m

s

s

s

µ

=C-H BENDING FUERA DEL PLANO

ALQUENOS

10 11 12 13 14 15

1000 900 800 700 cm-1

Monosustituidos

Disustituidos orto

meta

para

Trisustituidos

1,2,4

1,2,3

1,3,5

BENCENOS µ

s s

s

s s

s

s

s

s

m

m

m

m fdeP

ANILLO H’s

Bandas de combinación