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1.

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1) IR

-------------------------------- 3

2) 1H-NMR

--------------------------------

3)

13

C-NMR

4) UV-Visible
5) Mass

11

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20

--------------------------------

23

--------------------------------

25

--------------------------------

29

--------------------------------

34

- 1 -


l :

: , , , X-, , , ,
l
. (quantum).(, , )
, (photon) (quantum)
. E E = hv = hc/
( ) .
(quantumized)
.

. (spectrum)
( , A=log(I0/I)=cl )

H
C X

X+ Y

X H C X

E
X Y

X-ray

l 0.1nm -

X-H C X

C X
H
UV

Vis

200nm-400nm - 800nm

IR

2.5um --- 25um


4000cm-l --- 400cm-1

13C

Ho

O
H
H

Micro wave

13C

Radio wave

1m

5m

(spectrometer) .
l : NMR(Nuclear Magnetic Resonance), IR(InfraRed), UV-Vis, Mass
l .
- - (, Mass )-
l (HD) -

C H
(CnH2n+2) 2
.
, ,


- 2 -

1) IR
l : (IR, 8-40kJ/mol, 400-4000 cm-1)
(stretching vibration), (bending vibration) ,

.
l
.

()

,
n

= 4.12

K
m

K= ; , = [(m1xm2)/m1+m2]
, ,

IR spectrum
.
l : , , ,
reference

-1

( 3800-600 cm )

detecter

l
a. : .
b.

: ,

c. : IR .
d. :
e. : M-H

- 3 -

IR : cm-1

C-H:
C-H:
C-H:
C-H:
N-H:
O-H:
O-H:

A - H()
2900 (Alkyl)
3000 (Phenyl)
3100 (Alkenyl)
3300 (Alkynyl)
3200-3500
3300-3600()
2500-3300(COOH)

CA()

C=A()
C=C(Ar):1500-1600
C=C : 1600-1700

CC : 2100
CN : 2200

C=O
NO2

alkane

alkene

- 4 -

: 1650-1800
: 1500

C-X()
C-I : 500
C-Br : 600
C-Cl :700
C-C 800-1300

alkyne :1-Octyne

Alcohol

cf)carboxylic acid

- 5 -

1 Amine

2 Amine

- 6 -

- 7 -


A.

Ketone
Aldehyde

C=O
C=O

1715
1720

l ketone

l aldehyde

l conjugated systems

- 8 -

strong
strong

B.

- 9 -

- 10 -

2) H-NMR
l NMR
. , (1H)
13
C .
Element
Nuc lear spin
quantum
number ( I )
Number of
spin states

12

13

14

16

31

32

1/2

1/2

1/2

+ -

( -- ),
,
( , ), ()
.( )

no Ho
Ho

Ho

N
S

Ho N

Ho N

)
. =*/2
E'

E'

D E =E' - E = hv

hv
E

Ho

Ho

)
ex) 14093G 60MHz .
.
(nuclear magnetic resonance) .

. .
.
CH2
H3C

C
C
H2

CH2OH

C
H

H2
C

CH3
O

O
CHO

H2
C

CH3

H2
C

H2C

H
H

- 11 -

) ..

1.
.
. Z .
( ) .

)CH3CH2Cl , .
CH3CH2Cl CH2,
O
CH 3 CCH 3

C
H3 C

Cl
CH3 CHCl

CH 3

H3 C
Cl CH 2 CH 2 Cl

Cl
O

CH3
C

C
H

- 12 -

C
CH 3

2. (chemical shift) .:chemical shift .


,
.
2
shielded .
. (TMS)
(chemical shift) . chemical shift ppm .
TMS shielding .( 0 )

10

(deshielded), (shielded),

0 ppm
TMS

l Chemical shift

H

(deshielding)
CH3X
CH3F
EN of X
4.0
Chemical shift
4.26

CH3OH
3.5
3.40

CH3Cl
3.1
3.05

CH3Br
2.8
2.68

CH3I
2.5
2.16

CH4
2.1
0.23

(CH3)4Si
1.8
0

cf) NMR chemical shift . (0.5ppm )


3.37

0.96

1.33

0.96

O
0.96

3.24

1.50

1.33

(Magnetic Anisotropy)
- system - ,
.( deshielding
shielding.) shielding shielding
.
H
Bo

Bo

Bo

Bo

ppm

6-8

4-6

8-10

- 13 -

C H

2-3


. sp3
chemical shift ,
chemical shift . ( )

C
C C H
C

H
C C H
H

H
C C H
C

0d

1.33

4.08

H
2.01

O
1.57

0.96

. sp2
sp3
Vinyl H 4-6ppm, Aromatic H 6-8 ppm
. sp
C-H 2-3 ppm

proton carboxyl acid proton 10-12ppm ,
proton
proton -
proton
---------------------------------------------------------------------
ppm

ppm
RCOOH
10.5 -12.0
ArOH
4.0-7.0
ROH
0.5-5.0
RNH2
0.5-5.0
RCONH2
5.0-8.0
CH=CH-OH
> 15
---------------------------------------------------------------------l H-NMR

RCOOCH

chemical shift(ppm, )

3.7

- 14 -

- 15 -

3. (vicinal)
.
, .
)3 2 ,
2 3 .
2 .

4. .

.

- 16 -

1. ..

- 17 -

2. ester . .

- 18 -

3) 13 NMR :
l NMR (1.1%)
.
1. .
2. .

Type
N-C=O
OC=O
C=O

H-NMR

ppm
150-180
160-185
182-215

Type
=C-H
Ar C
NC

ppm
100-170
100-170
120-130

13

C-NMR

- 19 -

Type
-C-CH3
=C-CH3
X-CH2-O-CH3
C-H

ppm
0-50
10-50
10-65
50-90
60-90

22.8
14.0

35

30

25

20
PPM

- 20 -

15

22.8
14.0

34.7

10

26.4

13.6

O
9.1

172.0

59.5

180

160

140

120

100
PPM

80

60

40

20

59.5

O
39.1 173.0
129.9

135.0

13.6

O
129.9

128.9
127.3

180

160

140

120

128.9

100
PPM

- 21 -

80

60

40

20

4) UV-Visbile
l

l UV-Visbile Spectrum : , max.


max . , conjugated ststem

- 22 -

l Conjugated system

l
Dimethylpolyenes :CH3(CH=CH)nCH3 (a) n=3, (b) n=4, (c) n= 5

- 23 -

5)Mass Spectroscopy
l : .

(cation) (radical) .
) ethane

l (fragment) m/z
(/) ,
1 m/z cation .



.

l Mass Spectrum.
peak( detect ) 100 spectrum
(molecular) m/z
m/z ,

- 24 -

l : peak pattern .

l Mass Sp. with Bromine

l Mass Sp. with Chlorine

- 25 -

l Mass Sp.

l Mass Sp.

- 26 -

okmds.com

l Mass Sp.

l Mass Sp.

- 27 -

okmds.com

l
) (paracetamol, C8H9NO2) .
?
1

H-NMR (2.0, s), (6.8, d ), (7.3, d ), (9.2, s), (9.7, s )

chemical shift (ppm)


13

C-NMR (24, 115, 122, 132, 153, 168)

chemical shift (ppm)


IR (1667 cm1)

wavenumber (cm1)

NH2
O

H
N
O

OH

NH2

NH

HO

HO

- 28 -

HO

H
N

H
O

MeO

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05)
1

.
1

C3H6O2 , (IR) H-( H-NMR) .


IR

H-NMR ( 1.30, , 3H), ( 4.25,

, 2H), ( 8.05, , 1H)

O
H2C

OH
CH3

HO

O
CH2CH3

OCH2CH3

- 29 -

H3C

OCH3

H3C

CH2OH

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06). A (C4H10O) A B C .
A, B, C IR , A C ?

K2Cr2O7 / aq. H2SO4 PCC / CH2Cl2 H2 / Pd, EtOH H2O2 / H2O NaBH4 / EtOH

- 30 -

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06) C9H8O4 1H-NMR

13

C-NMR .

1H-NMR (300 MHz, CDCl3): 12.83(br s, 1H), 7.97(d, 7.8 Hz, 1H), 7.57(t,
7.32(t, 7.8 Hz, 1H), 7.11(d,
.)

7.8 Hz, 1H), 2.26(s, 3H). (,

7.8 Hz, 1H),

(long range coupling)

13C-NMR (75 MHz, CDCl3DMSO-d6): 168.9, 165.6, 150.4, 133.3, 131.4, 125.7, 124.1,
123.5, 20.9.

O
OCCH3

O
COCH3

COOH

COOH

COOH

OCCH3
O

- 31 -

COOH

COCH3
O

COOH

OCCH3
O

okmds.com

<>
O
Br

Mg

()

MgBr

1.

Ph

OH

OCH3
Ph

2. H3O

Ph

Ph

< >
(15 mL)() dropping funnel

(1) (0.73 g, 30 mmol)


100 mL 2 .
(2) Bromobenzene (4.0 g, 25 mmol)

(10 mL) dropping funnel

30 .
(3) Methyl benzoate

(10 mL) dropping funnel

.
(4) 30 (20 mL) H2SO4 (6 N, 5 mL)
(work-up) .
(5) (hexane)
.
(6) (IR)

OH

- 32 -

okmds.com

08) C3H6O <> < > .

O
H

O
C2H5

H3C

CH2

CH3

H3C
B

IR ( , cm1)

H
C

13

C NMR ( , ppm)

()

2950, 1250

73, 23

()

3100, 2900, 1650

153, 84, 55

()

2850, 2750, 1730

202, 37, 6

< > <> ?

- 33 -

okmds.com

Quiz

1. C4H8O Mass, IR NMR data ?

1H-NMR peak : 2.09(s) , 2.49(q),

1.06(t)

CH3

CH3OCH2CH=CH2

CH3COCH2CH3

CH3CH2CH2CHO

- 34 -

CH3CHCHO

CH3CH(OH)CH=CH2

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2. Mass, IR, 1H-NMR,

13

C-NMR .

1H NMR

70

: 3.53(t,), 1.52(h, 6), 0.96(t, ), 3.1()

60

50

propanoic acid 2-propanol

40

PPM

30

1-propanol

- 35 -

20

10

Ethyl methyl ether

okmds.com

3. C6H12O2 IR, 1H-NMR,

13

C-NMR .

? 1H-NMR peak .

CH3

CHO
H3C

H2C

CH3

H2C

CH3
O

CH3

CH3

H3 C

CH
HO

CH2CH3
O

C
C

H3 C

CH3
CH3
O

CH3

CH3
C
O

- 36 -

4 , 172 (mass unit)


M+2 .

IR, 1H-NMR,

13

C-NMR .

4-Bromophenol

4-Chlorophenol

3-Bromophenol

- 37 -

3-Chlorophenol

5. C11H14O. ?

H NMR :0.96(t,), 1.33(h, 6), 1.48(5) 2.98(d,3), 7.44-7.89( peak)

O
O

O
H
O

- 38 -

6. ?

H NMR :1.40(),

4.35(), 7.30, 4..46

COOCH2CH3

COCH2CH3

CH2CH2CN

CH

COOCH2CH3

HC

- 39 -

NH

7. ?
C5H10O2 .
IR 1740 cm-1 single peak

O
O

CH3

O
H3C

CH3

H3C

CH3

H3C

CH3
H3C

CH3

8. C10H12O2 .
IR 1711 cm-1 peak .
3.7 ppm peak singlet .

OCH3

CH2COCH3

4
PPM

H3CO

CH2COCH3

OCH3

OCH2CH2CH3

- 40 -

OCH3

OCH2CH2CH3

OCH2CH3

OCH2CH3

9. C9H11NO2 .
4.3 ppm 4.
7 ppm , , , .

OCH2CH3

OCH2CH3

OCH2CH3

OH

OH

NH2
CH3
N
CH3

NH2
NH2

- 41 -

H3C

CH3

10. C5H7NO2 .

O
O

NC
O

NH

NC

O
O

- 42 -

OH

NC
O

H2N