1.

MOLECULAR FORMULAS AND WHAT

CAN BE LEARNED FROM THEM
:

1.1 Elemental Analysis and calculations ( ) ⑧ Sump )e

②

③ ED 2

H2O

[☆ ?
ε
④
15

☆ H , Lempirisal 1a )

Sal 5 so fommualtyws]

( moleculan formulan
] K
(
□ SBCl J
☆
} [☆

☆
vmpoon ?

? ←

☆ ?

☆ ,

( ☆, S ]

9 . 83 mg - 6 :6

35
= .
mY

( 6
m

10 Dg

: CnH 402 C .4 lHz8 b 4

mass sBectrometry
3

CH 3 30 ) : C2 H 6
ex ) " Mass :
1.4 Index of Hydrogen Deficiency (

. ☆ [ NS , AsssbsBi )
β , 21□

EaHo CaHnal O ,

6 ( osS , sesTe ) )

H H H H

cidat
H
' t
-

↓
GaH 6 EaH 6 O

[δ , Cl , Br , f , ( )
7
←
⑥ )

HA *
←
Calto Calts

index [ ] " 1
,
1

↓ + ] 1
index ] 3 ⑨
2
s
2
,

index f 2
'

[E

inaleaz
②
)

indeal
①②
.

ex ] EaH 3 ClsO : CaH . ( CnHnta ) ←> H index <ω ) ←

0

high Nlas☆
resolution
1

1.5 The rule of thirteen ;

> 16, □ ,
←
 ⚫
2. INFRARED SPECTROSCOPY
IR / peak / /
heteroatom .

, α

i
λ

6600

L, (

□
,
in filp 2.3 The Modes of Stretching and Bending
uurwig

3, |E ☆

csot )

F HON0- LoMU 6G

‰ IO 0 E *☆ ☆β 20 □

,
=
; Daak

IR

4 C←
,
L3 6 , 28 orm , :Ce
Cisheagginghy?
4~
.
1250 gat )

symmetria
cm |
sum on2Sdum sfy( wavenombery : 4000 400
m
h : 2 .

2.1 The Infrared Absorption Process

IR , ,

(E)

(azb
d☆ S 3

LG CH . !

electrical 3

dipole ?

—> IR
electrical dipole peak

←
anhydriahe !

[3 9 D : FB X
L3 IR
▪

λ C OC EC =
CEE
← s

θ)

reduced mass

( ☆

bital
← , M☆ ☆ *

S $S 01 .
< 261
.

β
3

• s character

( , !)

C=O Stretching vibration at 1715 cm-1 ↓ ( 6)

]
Conjugated ketone : 1675-1680 cm-1 δ P' , >

β ? ←

atom negative charge

1700 ? ?
(?

360 □ 4

shar
↑
7
*

③
 ▪ ➡
[ X ]

tsharpo
stronay

Peas )
-

brodl

Tstrongabsorption 3200 ~ 3400

"
CH 3000 cm

+ 3
3ZD0 ~
3460

C=O present? 1820-1660 cm-1 -

CHE OH CH 3
if C=O is present
C

Acids Ot -
ClHa - .
CH 3

Amides N-H
medium absorption near 3400 cm-1
Esters C-O
strong absorption near 1300-1000 cm-1
Anhydrides two C=O
absorptions near 1810 & 1760 cm-1
θ Aldehydes aldehyde C-H
( broad )
two weak absorptions near 2850 & 2750 cm-1
Ketones ) <
!

other than preceding choices

If C=O is absent
Alcohols, phenols
O-H Broad absorption near 3400-3300 cm-1
C-O near 1300-1000 cm-1

Amines
N-H medium absorption near 3400 cm-1
Ethers
C-O near 1300-1000 cm-1,
absence of O-H (3400 cm-1)
🔷 Alkanes
∞
[ -

IH stretch 3000 ~
2840 Eml [ Sp3 ε -H )

1465
. ClHa bending cm
C← E !

cms 1000

bending
gow
ClHs 1B7s
= ) momosubstitode

1000 am

P
1B 7 S 4 CH .
"
770 cm

I 1 bg

30 O0

cig
s lid : EBr Ba E6 H3 ←
sample
Eliquiah :

'

7 OD

☆ Strain d

146 g

GSPrEH

Alkenes 31 Ocmi "

□ NO

EIHstretah 309s ~ 3010 cm !

"
= ( SP ← H )

CIt 650
out of plane Loop) bending 1000 ~
-
am

)
,

o
C← G stretah 1660 ~
1600 cml

s Eoj ugaation C= C
,
FR

3 (twams )
←

G97

C=C trans
C - C stretah : 1 b7on 1640 aml traps s 167 □ aml

cis 1688 ] strams

3 cm [ 53 symmetry weak peak Cb

conjugation effects
-conjugation compound Alkynes
D !
B EE - It stretch 3300 cm ( sPE -H )
λ

.
EEC stretch 2150 cl
simgle boml amanwnater

Esbwocm
"
s conjugation C
, disubstitwted or
symmetr.

The C-H out-of-plane bending vibrations for substituted

alkenes
-IR 6
"
Z/S ω cm

33 D 0 cm

IOOD , IOO

no

← symmetry A
G 7□
Beals X

8go

81

λ 1600 cm OOP X ☆ tefrasubstituteal

Σ
▪
▪ ▪

Aromatic rings

=C-H stretch 3000 cm-1 (sp2 C-H)

=C-H out-of-plane (oop) bending 900~690 cm-1
monosubstituted rings 690, 750 cm-1
[ ↓ 0 ortho-disubstituted rings 750 cm-1
meta-disubstituted rings 690, 780, 880 cm-1
para-disubstituted rings 800~850 cm-1
Ring-Size effects with internal double bonds —> aromatic rings
- 90 , C=C stretch 1600~1475 cm-1
60

OvelaPX X

☆ ovevlup IOOO IKARg

7S□ G9 D

↑3 10
{
9.
E 600

Ring-Size effects with external double bonds

-

- ,
880

780 69 D

ring

800 ~
85b

cohjugantion
☆
×
▪🔷 ➡

Alcohols and Phenols

free O-H stretch : sharp peak 3650~3600 cm-1
- solvent

hydrogen-bonded O-H stretch : broad peak 3400~3300 cm-1

- O-H
-

C-O-H bending : broad, weak 1440~1220 cm-1

C-O stretch 1260~1000 cm-1

(4 ( Hz)

72□ Em

J 260 v 3 DOD

800 ~
88 so
| V60 ~ l 47 S
BOG MOND

if sample peak ?

peako ( y . dry sample

oven1 ,

IR N 2 , EO 2 .

salvet

isolantion ? *
isolantion

solventoll dilute (n ) ←> Mydrgen bonding