1. AOIJAI WICHAISIRI

2.  isomerism
 isomer
 C2H6O
CH3–CH2–OH O CH3–O–CH3 O
 C3H6O H3C C CH3 H3C CH2 C H
¤Õ
âµ¹ áÍÅ äδì
´Õ

4. Structural
isomer
skeleton
isomer
positional isomer
functional
isomer
Stereo isomer)
(configuration)

5. Structural isomer
skeleton
isomer



 CH CH
 CH CH
 CH C H

6. C H

7. positional isomer

 C4H10O positional isomer

8. functional
isomer


CHO functional isomer
O O
 CHO
functional isomer 2
H C CH CH3 H3C C CH3
propanal propanone

9. Stereo isomer)
geometrical
isomer

 - (cis-trans isomer)
H
H3C CH 3 H3C H
C C C C
H H H CH 3
cis- 2-butene trans-2-butene

10. optical isomer

(polarized light)
(asymmetry)
 C
chiral carbon
 C
Br Br
achiral carbon
* C C
Cl H H 3C H
H 3C H 3C

11. Achiral molecule

plane of polarized
light

optically inactive

12. Chiral molecule


optically active

13. Achiral carbon
•
superimposible
Chiral carbon
•
non-
superimposible
Br Br Br Br
C C C C
H H H H Cl H Cl H
H3C CH3 H3C CH3
ËÁ 120ͧÈ
¹
Ø Ò

14. Chirality Center
Carbon has four different groups attached

15. CH CH
Geometrica
C=C
H Cl
Geometrical isomer C=C
cis trans E
E Z Sequenc
priority

16. Sequence rules
p
Br > 17Cl > 8O > 7N > 6C > 1
multiple bond
H H H H HH
-C=O -C-O -C=C- -C-C-
OC C C

17. Hi CH CH L
C=C
L H Cl Hi
E- -chloro- -pentene E-iso
Sequence rules
C=C -
priority Hi
priority L
priority Hi L Z
priority Hi L E

18. L CH CH OH L
C=C
Hi CH CH Cl Hi
Z
E Hi CHZ-
Z?
CH OH Hi
isomer C=C
L H CH(CH L
Z Z-isomer

19. COOH COOH
HO H OH CH
CH
H
-(-)-Lactic acid R
R S? priority
fischer projection
Sequence rules , 2, 3
OH
1, 2
CH3
R
S

20. Br Br
NC H
NC CH
H CH
R
fischer projection
priority , 2, 3
S
R

21. CH=CH CH=CH
H CH CH
H CO H
CH CH CO H
S
fischer projection
priority
fischer projection 3
, 2,
2. priority , 2, 3 R
?
S

22. Fischer projection
Fischer projection

23. Diastereomers
• stereoisomers
mirror images
•
•
• chiral
centers
• n chiral center
n
stereoisomers
23

24. C H3
C H3
Enanti
omer
H C Br Br C H
H C Br Br C H
C 2H 5 C 2H 5
1 2 Diaster
Diaster
eomer C H3 C H3
eomer
Br C H H C Br
H C Br Br C H
C 2H 5 C 2H 5
Enanti
3 omer
4
24

25. Meso compounds
• chiral centers
stereoisomers
• * *
,3-dibromobutane
C H 3C HC HC H 3
stereoisomers
Br Br
C H3 C H3 C H3 C H3
Br C H H C Br H C Br Br C H
H C Br Br C H H C Br Br C H
C H3 C H3 C H3 C H3
A B C D
25

26. C H3 C H3
Br C H Enanti H C Br
H C Br
omer Br C H
C H3 C H3
A B
Diaster Diaster
eomer C H3
eomer
H C Br
H C Br
C H3
C
Moso
compoun 26

27. chiral cen
• configuration
chiral center (S) (R)
• Stereoisomer A
CH 3 ,3-
Br
(R) H
dibromobutane
C C-2 C-3
chiral centers3R)- ,3-
(R) Br (2R,
H C
configurationdibromobutane
(R)
C H3
27

28. (R )
HO C H (S )
H C OH
(S )
C H 3NH C H (R )
H C NHC H 3
C H3 C H3
(1R,2S)-(-)-Ephedrine
(1S,2R)-(+)-Ephedrine
(S ) (R )
H C OH HO C H
(S ) (R )
C H 3NH C H H C NHC H 3
C H3 C H3
1S,2S)-(+)-Pseudophedrine Pseudophedrine
(1R,2R)-(-)-
28

29. 1. substitution
reaction )
OH + CH3CH2 Cl CH3CH2OH + Cl
นิ ลีอฟ
วค โ ไ ล สรตั้ ต้
า งน สรผ ต ณ ์ อิ อ ที่
า ลิ ภั ฑ อ น
หด อ
ลุ อ ก
H H2SO4
NO2
+ HNO3 + H2O

30. (Addition
reaction)
C C + A B C C
A B
CH2 CH2 + Cl2 CH2 CH2
Cl Cl
CH3CH CH2 + Br2 CH3CH CH2
Br Br

31. Elimination
reaction)
X
C C C C + X
(HX)
H
Nu
CH3CH2 Br + OH CH2 CH2 + H2O + Br
(HBr)

32. H
Lewis base
C C C C + H2O
OH
H2SO4
CH3 CH2 OH CH2 CH2 + H2O
ethanol ethene

33. Oxidation
reaction)
K2Cr2O7/H2 SO4
CH3 CH OH CH3 C O
CH3 CH3
OH K2Cr2O7
O
H +
H

34. Reduction
reaction)
O H
LiAlH4
CH3CH2 C OH CH3CH2 C OH
H
H2/ Pd
CH3 CH2 CH CH2 CH3 CH2 CH2 CH3

35. 6.
rearrangement reaction )
heat, catalyst
CH3 CH2 CH2 CH3 CH3 CH CH3
CH3
heat, catalyst
CH3 CH2 CH CH2 CH3 C CH2
CH3

36. Polymerization) Cl
nCH2 CH Cl (CH2 CH)
n
vinyl chloride polyvinyl chloride
nCH2 CH2 ( CH2 CH2 )n
ethylene polyethylene