1

à¤ÁÕÍÔ¹·ÃՏÊíÒ¤ÑÞÍ‹ҧäà !!!
- ໚¹ÊÒûÃСͺ·ÕèÊíÒ¤ÑÞã¹ÊÔè§ÁÕªÕÇÔµ
- ¹íÒä»ãªŒä´ŒËÅÒ¡ËÅÒ ઋ¹ ÍÒËÒà ÂÒ ¹éíÒÁѹ ¾ÅÒʵԡ à¤Ã×èͧÊíÒÍÒ§ ÏÅÏ
à¤ÁÕÍÔ¹·ÃՏ ÊÒ¢ÒÇÔªÒ·Õèà¡ÕèÂÇ¢ŒÍ§¡Ñº¡ÒÃÈÖ¡ÉÒà¡ÕèÂǡѺ ÊÒÃÍÔ¹·ÃՏ ÊÒûÃСͺ·ÕèÁոҵؤÒϺ͹໚¹
ª¹Ô´ ÊÁºÑµÔ ¡ÒÃÊѧà¤ÃÒÐˏ áÅл¯Ô¡ÔÃÔÂҢͧÊÒûÃСͺ ͧ¤»ÃСͺ ·Ñ駷Õèà¡Ô´¨Ò¡ÊÔ§è ÁÕªÕÇÔµ áÅШҡ¡ÒÃÊѧà¤ÃÒÐˏ
ÍÔ¹·ÃՏ
ÊÒÃ͹Թ·ÃՏ ÊÒ÷ÕèäÁ‹ä´Œ»ÃСͺ´ŒÇ¸ҵؤÒϺ͹áÅÐäÎâ´Ãਹ / ÊÒ÷Õèä´Œ¨Ò¡ÊÔè§äÁ‹ÁÕªÕÇԵઋ¹ ËÔ¹ áË¸ÒµØ ໚¹µŒ¹
ÊÒÃÍÔ¹·ÃՏ໚¹ÊÒûÃСͺ·ÕèÁոҵؤÒϺ͹໚¹Í§¤»ÃСͺ ¡àÇŒ¹!!! ÊÒôѧµ‹Í仹Õé
1. ÊÒ÷Õè໚¹ÍÑÞÃÙ»¢Í§¸ÒµØ¤ÒϺ͹ ઋ¹ ྪà á¡Ã俵 ¿ÅÙàÅÍÃÕ¹
2. ÍÍ¡ä«´¢Í§¤ÒϺ͹ ઋ¹ CO, CO2
3. ¡Ã´¤ÒϺ͹ԡ (H2CO3) à¡Å×ͤÒϺÍ๵áÅÐäÎâ´Ãਹ¤ÒϺÍ๵ (CO32-, HCO3- ) ઋ¹ NaHCO3 , CaCO3
4. à¡Å×ÍÍÍ¡«Òàŵ (C2O42-) ઋ¹ Na2C2O4
5. à¡Å×Íä«ÂÒä¹´ à¡Å×Íä«ÂÒ๵ à¡Å×Íä·âÍä«ÂÒ๵ (CN, OCN-, SCN-) ઋ¹ KCN , NH4OCN , KSCN
6. à¡Å×ͤÒÏ亴 ઋ¹ CaC2
7. ÊÒûÃСͺ¤ÒϺ͹ºÒ§ª¹Ô´ ¾Ç¡«ÑÅä¿´ (S2-) ¤ÅÍäô (Cl-) ઋ¹ CCl4 , CS2, COCl2

¢ŒÍã´äÁ‹¨Ñ´à»š¹ÊÒÃÍÔ¹·ÃՏ
1. CH4 (ᡍÊÁÕà·¹) 6. CH2O (¿ÍÏÁÒÅ´Õäδ)
2. C12H22O11 (¹éíÒµÒÅ·ÃÒÂ) 7. NH2CONH2 (ÂÙàÃÕÂ)
3. CH3NH2 (àÁ·ÔÅàÍÁÕ¹) 8. HCOOH (¡Ã´Á´)
4. CO2 (¤ÒϺ͹ä´ÍÍ¡ä«´) 9. HCN (äÎâ´Ãਹä«ÂÒä¹´)
5. C8H9NO2 (ÂÒ¾ÒÃÒ૵ÒÁÍÅ) 10. CaCO3 (ËÔ¹»Ù¹)
6. ệ§ÁѹÊíÒ»ÐËÅѧ 11. CaC2 (¶‹Ò¹á¡Ê)
7. ã¾ת 12. C60
8. ᡍÊËاµŒÁ 13. C6H12O6 (¹éíÒµÒÅ¡ÅÙâ¤Ê)
9. ¶‹Ò¹ËÔ¹ 14. NaHCO3 (¼§¿Ù)
 2

ËÑÇ¢ŒÍ·Õè 1. ¾Ñ¹¸Ð¢Í§¤ÒϺ͹ã¹ÊÒûÃСͺÍÔ¹·ÃՏ
¡ÒÃà¡Ô´¾Ñ¹¸Ð¢Í§¤ÒϺ͹ 6C (2 , 4) (1s2 2s2 2p2)
C ¸ÒµØËÁÙ‹ IVA ÁÕ Valence e- = 4 à¡Ô´¾Ñ¹¸Ðâ¤àÇàŹµä´Œ 4 ¾Ñ¹¸Ð

sp2
sp 3
sp sp
H N O F

·º·Ç¹ÊÙµÃâ¤Ã§ÊÌҧẺ¨Ø´áÅÐàÊŒ¹¢Í§ÅÔÇÍÔÊ

___H2O Cl2 NH4+ ໚¹ÊÒÃâ¤àÇàŹµ

___CH3OCH3 Áվѹ¸ÐäÎâ´Ãਹ

___CH3OH Áըشà´×Í´ÊÙ§¡Ç‹Ò CH3CH3

___CCl4 ໚¹âÁàÅ¡ØÅäÁ‹ÁÕ¢ÑéÇ

___CH3COOH Áվѹ¸ÐäÎâ´Ãਹ෋ҹÑé¹

___CH3Br ¨Ø´à´×Í´ÊÙ§¡Ç‹Ò CH3Cl à¾ÃÒÐÁÕ¢ÑéÇÁÒ¡¡Ç‹Ò

 3

¡ÒÃà¼ÒäËÁŒ
- à¼ÒäËÁŒÊÁºÙó(¡ÒÃÊѹ´Ò») ¨Ðä´Œ CO2 + H2O
- à¼ÒäËÁŒäÁ‹ÊÁºÙó ¨Ðä´Œ CO + H2O
CH4 + O2 →

C2H6 + O2 →

ËÑÇ¢ŒÍ·Õè 2. â¤Ã§ÊÌҧ¢Í§ÊÒûÃСͺÍÔ¹·ÃՏ
·º·Ç¹àÃ×èͧ¾Ñ¹¸Ðà¤ÁÕ (ª¹Ô´¢Í§¾Ñ¹¸Ð)
1. ¾Ñ¹¸Ðà´ÕèÂÇ (Single bond)

2. ¾Ñ¹¸Ð¤Ù‹ (Double bond)

3. ¾Ñ¹¸ÐÊÒÁ (Triple bond)

¡ÒÃà¢Õ¹ÊÙµÃâ¤Ã§ÊÌҧÊÒûÃСͺÍÔ¹·ÃՏ
â¤Ã§ÊÌҧÅÔÇÍÔÊ
ª×èÍÊÒà ÊÙµÃâÁàÅ¡ØÅ
Ẻ¨Ø´ ẺàÊŒ¹
H H

ÍÕà·¹ C2H6 H C C H

H H

H H
ÍÕ·Õ¹ (àÍ·ÔÅÕ¹) C2H4 C C
H H

ÍÕä·¹ (ÍÐà«·ÔÅÕ¹) C2H2 H C C H

äÎâ´Ãਹä«ÂÒä¹´ HCN

àÁ·Ò¹ÒÁÕ¹ CH5N
 4

â¤Ã§ÊÌҧÅÔÇÍÔÊ
ª×èÍÊÒà ÊÙµÃâÁàÅ¡ØÅ
Ẻ¨Ø´ ẺàÊŒ¹

àÍ·Ò¹ÍÅ
C2H6O
ËÃ×Íä´àÁ·ÔÅÍÕà·ÍÏ

ÁÕà·¹ CH4

Êٵ÷ҧà¤ÁբͧÊÒûÃСͺÍÔ¹·ÃՏ

ÊÙµÃâ¤Ã§ÊÌҧ
ÊÙµÃâÁàÅ¡ØÅ

(ÅÔÇÍÔÊ)

(Ẻ‹Í)

(ẺàÊŒ¹¾Ñ¹¸Ð)

⫋ແ´ â«‹»´

â«‹µÃ§ â«‹¡§Ôè ǧ
 5

ÊÙµÃâ¤Ã§ÊÌҧ (Structural formula) ໚¹Êٵ÷ÕèáÊ´§¡ÒèѴàÃÕ§ÍеÍÁ¢Í§¸ÒµØµ‹Ò§æ ã¹âÁàÅ¡ØÅ

¢Í§ÊÒùÑé¹
ÊÙµÃâ¤Ã§ÊÃŒÒ§áººÂ‹Í (Condense structural formula) äÁ‹áÊ´§¾Ñ¹¸ÐÃÐËÇ‹Ò§ C-H ÊÒÁÒö‹Í
¾Ñ¹¸Ðà´ÕèÂÇä´Œ·Ñé§ËÁ´ËÃ×Í‹ͺҧʋǹ â´Â¾Ñ¹¸Ð¤Ù‹áÅоѹ¸ÐÊÒÁ¨ÐÂѧ¤§äÇŒ
ª×Íè ÊÒà / ÊÙµÃâ¤Ã§ÊÌҧ
ÊÙµÃâÁàÅ¡ØÅ â¤Ã§ÊÌҧÅÔÇÍÔÊ â¤Ã§ÊÌҧẺ‹Í
ྐྵ෹ H H H H H
CH3CH2CH2CH2CH3 ËÃ×Í
C5H12 H C C C C C H

H H H H H
CH3(CH2)3CH3
2– àÁ·ÔźÔÇà·¹
(äÍâ«à¾¹à·¹) H H H H H
(CH3)2CH(CH2)2CH3
C5H12 H C C C C C H

H H H H

H C H

ྐྵ·Õ¹
C5H10 H H H H

C C C C C H

H H H H H

ä«â¤ÅàΡૹ
C6H12 H
H
C
H
H

H C C H

H C C H
H C H
H H

â¾Ã¾Òâ¹¹
(áÍ«Õâµ¹) H O H

H C C C H
C3H6O
H H

àÍ·Ò¹ÍÅ H H

C2H6O H C C O H

H H
 6

ª×Íè ÊÒà / ÊÙµÃâ¤Ã§ÊÌҧ

ÊÙµÃâÁàÅ¡ØÅ â¤Ã§ÊÌҧÅÔÇÍÔÊ â¤Ã§ÊÌҧẺ‹Í
àÁ·Ò¹ÒÅ
(¿ÍÏÁÒÅ´Õäδ) O

CH2O H C H

ÍÐà«·ÔÅÕ¹

C2H2
àÁ·Ò¹ÍÅ

CH4O
àÁ·Ò¹ÒÁÕ¹

CH5N

CH3CH=C(CH3)2

ÊÙµÃâ¤Ã§ÊÌҧẺàÊŒ¹¾Ñ¹¸Ð (Bond-Line structural formula)

- 㪌àÊŒ¹µÃ§á·¹¾Ñ¹¸ÐÃÐËÇ‹Ò§¤ÒϺ͹
- ¶ŒÒÁÕ¨íҹǹ C µ‹Í¡Ñ¹ÁÒ¡¡Ç‹Ò 2 ÍеÍÁãˌ㪌àÊŒ¹µ‹Í¡Ñ¹áºº«Ô¡á«¡
- ᵋÅÐÁØÁ¢Í§ÊÒÂâ«‹á·¹ÍеÍÁ¢Í§ C ·Õ赋ÍÍÂÙ‹¡Ñº H 㹨íҹǹ·Õè·íÒãËŒ C ÁÕ Ve- ¤Ãº 8
- ¸ÒµØÍ×è¹·ÕèäÁ‹ãª‹ C áÅÐ H äÁ‹ÊÒÁÒö‹Íä´Œ µŒÍ§à¢Õ¹¸ÒµØ¹Ñé¹Å§ä»´ŒÇÂ
CH2=CHCH2CH3

CH2 CH3

CH3 CH CH CH CH3
 7
H2
C
H2C CH

H2C CH
C
H2

H H

H C C H

H H

¨§à¢Õ¹ÊÙµÃâ¤Ã§ÊÃŒÒ§áººÂ‹Í ¡ÑºáººàÊŒ¹¾Ñ¹¸Ð¢Í§ÊÒûÃСͺÍÔ¹·ÃÕµ Í‹ 仹Õé

¢ŒÍ â¤Ã§ÊÌҧÅÔÇÍÔÊ â¤Ã§ÊÃŒÒ§áººÂ‹Í â¤Ã§ÊÌҧẺàÊŒ¹¾Ñ¹¸Ð

H H H H H H

1 H C C C C C C H

H H H H H H

H C H

2 H H H H H

H C C C C C C H

H H H H

H C H

3 H H H

H C C C C C C H

H H H
H C H

H C H
H H H H H

H C C C C C C H
4 H H H H
H C HH C H

H H
 8

¢ŒÍ â¤Ã§ÊÌҧÅÔÇÍÔÊ â¤Ã§ÊÃŒÒ§áººÂ‹Í â¤Ã§ÊÌҧẺàÊŒ¹áÅÐÁØÁ

O H
C N
5
H C C H
H H

H C H
H

H C H H C H

6 H H H H

H C C C C C C H

H H H H H
H C H

H H H H H

7 H C C C C C H

H H H

8 CH3CH=C(CH3)2

9 (CH3)2O ËÃ×Í CH3OCH3

10 CH3CHCl2
 9

ËÑÇ¢ŒÍ·Õè 3. ËÁÙ‹¿˜§¡ªÑ¹ (Functional group)

ËÁÙ‹¿§˜ ¡ª¹Ñ ¤×Í Ê‹Ç¹¢Í§â¤Ã§ÊÌҧ·ÕèáÊ´§ÊÁºÑµÔ੾ÒТͧÊÒûÃСͺÍÔ¹·ÃՏ»ÃÐàÀ·¹Ñé¹æ
ÊÒûÃСͺÍÔ¹·ÃՏ
ÊÒûÃСͺÍÔ¹·ÃÕ· ÕèÁ¸Õ ÒµØ O ÊÒûÃСͺÍÔ¹·ÃÕ· ÕèÁ¸Õ ÒµØ N
ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹
໚¹Í§¤»ÃСͺ ໚¹Í§¤»ÃСͺ
Alkane Alcohol Amine
Alkene Ether Amide
Alkyne Aldehyde
Aromatic hydrocarbon Ketone
**ÊÒûÃСͺÍÔèÁµÑÇ Carboxylic acid
(Saturated hydrocarbon) Ester
**ÊÒûÃСͺäÁ‹ÍÔèÁµÑÇ
(Unsaturated hydrocarbon)
ǧ¡ÅÁÅŒÍÁÃͺËÁÙ‹¿˜§¡ªÑè¹

Ãкبíҹǹ 1. C=C…………….ËÁÙ‹ 2. ……………..ËÁÙ‹

3. O-H ……………ËÁÙ‹ 4. ................ËÁÙ‹

5. ...........ËÁÙ‹ 6. ..........ËÁÙ‹
 10

¢ŒÍ ÊÙµÃâ¤Ã§ÊÌҧ »ÃÐàÀ·¢Í§ÊÒÃ

1. CH3CH2CHO
2. CH3(CH2)2OH
3. CH3(CH2)2COOH
4. CH3COOCH2CH3
 11

¢ŒÍ ÊÙµÃâ¤Ã§ÊÌҧ »ÃÐàÀ·¢Í§ÊÒÃ

5. CH3CO(CH2)2CH3
6. CH3CH2OCH2CH3
7.

8.

9.
10.

11.

12.

ËÑÇ¢ŒÍ·Õè 4. ª×èͧ͢ÊÒûÃСͺÍÔ¹·ÃՏ
ª×Íè ÊÒÁÑÞ ª×Íè µÒÁÃкº IUPAC
¡ÒÃàÃÕ¡ª×Íè µÒÁáËÅ‹§·Õ辺 ÅѡɳРª×èͼٌ¤Œ¹¾º ¡ÒÃàÃÕ¡ª×èÍ·ÕèÁÕ¤ÇÒÁÊÑÁ¾Ñ¹¸¡Ñºâ¤Ã§ÊÌҧÍ‹ҧ໚¹Ãкº
¤íÒ¹íÒ˹ŒÒ + â«‹ËÅÑ¡ + ¤íÒŧ·ŒÒÂ
(prefix) (main chain) (suffix)
ËÁÙ‹á·¹·Õè ¨íҹǹ C ËÁÙ‹¿§˜ ¡ª¹Ñ
¨ØÅÀÒ¤ (,) ÂѵÀÔ §Ñ ¤ (-)
µÑÇàÅ¢,µÑÇàÅ¢ µÑÇàÅ¢-µÑÇÍÑ¡ÉÃ

2-fluoropentane 4-propyloctane
 12

¤íÒ¹íÒ˹ŒÒ (prefix) ËÁÙá‹ ·¹·Õè

-R
(Alkyl)

-OR -OH -NH2 -NO2

(alkoxy) (hydroxy) (amino) (nitro)
-OCH3
-X -Cl -Br -F -I
(ËÁÙ‹ 7 (chloro) (bromo) (Fluoro) (Iodo)
halogen)
*** ¶ŒÒÁÕËÁÙ‹á·¹·Õè ·Õ«è Òéí ¡Ñ¹ÁÒ¡¡Ç‹Ò 1 ËÁÙ‹
¨íҹǹËÁÙá‹ ·¹·Õ·è «Õè Òéí ¡ÒÃàÃÕ¡ËÁÙ·‹ «Õè Òéí
2 di-
3 tri-
4 tetra-
5 penta-
â«‹ËÅÑ¡ (main chain) ¨íҹǹ C
äÁ‹ÁËÕ ÁÙ¿‹ ˜§¡ª¹Ñ ÁÕËÁÙ¿‹ §˜ ¡ª¹Ñ
àÅ×Í¡â«‹·ÕèÂÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡ àÅ×Í¡â«‹·ÕèÂÒÇ·ÕèÊØ´áÅÐÁÕËÁÙ‹¿˜§¡ªÑ¹ÍÂÙ‹´ŒÇÂ
¨íҹǹ C ¤íÒ¹íÒ˹ŒÒ ÍÍ¡àÊÕ§
1 meth- ÁÕ· ËÃ×Í àÁ·
2 eth- ÍÕ· ËÃ×Í àÍ·
3 prop- â¾Ã¾
4 but- ºÔÇ·
5 pent- ྐྵ·
6 hex- àΡ«
7 hept- àλ·
8 oct- ÍÍ¡·
9 non- â¹¹
10 dec- à´¡¤
11 undec- Íѹഡ¤
12 dodec- â´à´¡¤
 13

¤íÒŧ·ŒÒ (suffix) ËÁÙ¿‹ §˜ ¡ª¹Ñ

à¢Õ¹µÒÁª¹Ô´¢Í§ÊÒÃÍÔ¹·ÃՏ
ª¹Ô´¢Í§ÊÒà ¤íÒŧ·ŒÒ ª¹Ô´¢Í§ÊÒà ¤íÒŧ·ŒÒ ª¹Ô´¢Í§ÊÒà ¤íÒŧ·ŒÒÂ
Alkane -ane Alcohol -ol Amine -amine
Alkene -ene Ether -OR’ = -oxy Amide -amide
Alkyne -yne -R = -ane
Aromatic - Aldehyde -al
Ketone -one
Carboxylic acid -oic acid
Ester -oate
¢ŒÍ¤ÇÃÃÙàŒ ¾ÔÁè àµÔÁà¡ÕÂè ǡѺÊÒà Aromatic (µŒÍ§ÁÕ¤³
Ø ÊÁºÑµ¤Ô ú¨Ö§¨Ð໚¹ Aromatic ä´Œ)
1. µŒÍ§à»š¹Ç§ µŒÍ§áº¹ÃÒº
2. µŒÍ§ÁÕÃкº¤Í¹¨Ùà¡·Í‹ҧÊÁºÙó (Áվѹ¸Ð¤Ù‹ÊÅѺà´ÕèÂÇ , e- à¤Å×è͹·Õè)
3. µŒÍ§ÁÕ π-electron = 4n+2 àÁ×èÍ n=1,2,3,… (¤×͵ŒÍ§ÁÕ π-electron = 6 , 10 , 14 ,………)

1. ¡ÒÃàÃÕ¡ª×Íè áÍÅह (Alkane) Êٵ÷ÑÇè ä» CnH2n+2 “ŧ·ŒÒ´ŒÇ –ane”

ª×Íè ÊÒÁÑÞ ª×Íè µÒÁÃкº IUPAC
1. àÅ×Í¡â«‹·ÕèÂÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡
2. ãËŒ¡Ôè§à»š¹µíÒá˹‹§·Õè¹ÍŒ ·ÕèÊØ´

IUPAC

CH3 CH2 CH3 CH3 CH3 CH2 CH3 CH3

1 2

CH3 CH CH C CH3 CH3 CH CH C CH3

1 2 3 4 5 3 4 5 6
CH3 CH3
 
 14

IUPAC
¶ŒÒâ«‹ËÅÑ¡ÁÕä´ŒËÅÒÂẺ ãËŒàÅ×͡Ẻ·ÕèÁÕ¨íҹǹËÁÙ‹áÍŤÔÅÁÒ¡¡Ç‹Ò໚¹â«‹ËÅÑ¡
CH3 CH2 CH3 CH3
1 2

CH3 CH CH CH CH CH2 CH3 CH3 CH2 CH3 CH3

3 4 5 1 2

CH2 CH2 CH3 CH3 CH CH CH CH CH2 CH3

6 7 8 3 4 5 6 7 8
CH2 CH2 CH3

 
IUPAC
¡íÒ˹´µÑÇàÅ¢áÊ´§µíÒá˹‹§¢Í§¤ÒϺ͹ã¹â«‹ËÅÑ¡ â´ÂàÃÔèÁ¨Ò¡»ÅÒ´ŒÒ¹ã´¡çä´Œ·Õè·Òí ãËŒËÁÙá‹ ÍŤÔÅÍÂÙ‹ã¹µíÒá˹‹§·Õè
ÁÕµÑÇàÅ¢¹ŒÍÂæ

¶ŒÒËÁÙ‹áÍŤÔŵ‹ÍÍÂÙ‹¡Ñºâ«‹ËÅÑ¡äÁ‹àËÁ×͹¡Ñ¹ãËŒàÃÕ¡ª×èÍàÃÕ§ÅíҴѺËÁÙ‹áÍŤÔŵÒÁÅíҴѺÍÑ¡ÉÃÀÒÉÒÍѧ¡ÄÉ áÅÐÃкØ
µÑÇàÅ¢áÊ´§µíÒá˹‹§änj˹ŒÒª×èÍËÁÙ‹áÍŤÔŠઋ¹

CH3

CH3 CH2 CH2 CH3

1 2

CH3 CH CH CH CH CH2 CH3

3 4 5 6 7 8

CH2 CH2 CH3

4 –ethyl– 3, 6 – dimethyl – 5 –propyloctane

CH3

CH3 CH2 CH3

CH3 CH CH CH CH CH2 CH3

1 2 3 4 5 6 7

CH2 CH2 CH3

3 – ethyl – 2, 5 – dimethyl – 4 –propylheptane

 15

¢ŒÍã´Í‹Ò¹ª×èÍä´Œ¶Ù¡µŒÍ§

¨§à¢Õ¹ÊÙµÃ/Í‹Ò¹ª×Íè
¢ŒÍ ª×Íè â¤Ã§ÊÌҧ
1 hexane

2 3 – ethylhexane

3 2,2,4 – trimethylpentane

4 4 – ethyl – 2,2 – dimethyloctane

5
CH3

CH3 CH CH CH2 CH3

CH2 CH3

6
CH3

CH3 CH2 CH CH CH3

CH2 CH3

7
 16

¢ŒÍ ª×Íè â¤Ã§ÊÌҧ

8
CH3CH2C(CH3) 2CH2CH3

9 3-isopropyl-2,4-dimethylpentane

10 2,4-dimethylhexane

11

12 3-ethyl-2,4-dimethylhexane

13

14

15
 17

1.1 ¡ÒÃàÃÕ¡ª×Íè ä«â¤ÅáÍÅह (Cycloalkane) Êٵ÷ÑèÇä» CnH2n “¹íÒ˹ŒÒ´ŒÇ Cyclo ŧ·ŒÒ´ŒÇ –ane”
â¤Ã§ÊÌҧ ª×Íè ÊÒÃ

3-cyclobutylpentane

1,2-dimethylcyclopropane

1,3-dimethylcyclobutane
 18

2. ¡ÒÃàÃÕ¡ª×Íè áÍŤչ (Alkene) Êٵ÷ÑÇè ä» CnH2n “ŧ·ŒÒ´ŒÇ –ene”

ª×Íè ÊÒÁÑÞ ª×Íè µÒÁÃкº IUPAC
ÊÙµÃâ¤Ã§ÊÌҧ ª×Íè ÊÒÁÑÞ 1. àÅ×Í¡â«‹·ÁÕè վѹ¸Ð¤Ù‹·ÂÕè ÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡
CH2=CH2 àÍ·ÔÅÕ¹ (ethylene) 2. ãËŒ¾Ñ¹¸Ð¤Ù‹à»š¹µíÒá˹‹§·Õ¹è ŒÍ·ÕèÊØ´
CH3
CH2=CH–CH3 â¾Ã¾ÔÅÕ¹ (propylene)
5 4 3 2 1
CH2=CH–CH2–CH3 ºÔÇ·ÔÅÕ¹ (butylenes) CH3 CH2 C CH CH3

CH2=CH–CH3 äÍ⫺ÔÇ·ÔÅÕ¹ (isobutylene)

CH3
¢ŒÍ ª×Íè â¤Ã§ÊÌҧ
1

7
 19

1.2 ¡ÒÃàÃÕ¡ª×Íè ä«â¤ÅáÍŤչ (Cycloalkene) Êٵ÷ÑèÇä» CnH2n-2 “¹íÒ˹ŒÒ´ŒÇ Cyclo ŧ·ŒÒ´ŒÇ –ene”
ª×Íè µÒÁÃкº IUPAC

- ãËŒ¾Ñ¹¸Ð¤Ù‹à»š¹µíÒá˹‹§¹ŒÍ·ÕèÊØ´
- ¹íÒ˹ŒÒ´ŒÇ cyclo ŧ·ŒÒ´ŒÇ –ene

¢ŒÍ ª×Íè â¤Ã§ÊÌҧ

1

4
 20

3. ¡ÒÃàÃÕ¡ª×Íè áÍÅ䤹 (Alkyne) Êٵ÷ÑÇè ä» CnH2n-2 “ŧ·ŒÒ´ŒÇ –yne”

ËÅÑ¡¡ÒÃ
1. àÅ×Í¡â«‹·ÕèÁվѹ¸ÐÊÒÁ·ÕèÂÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡
2. ãËŒ¾Ñ¹¸ÐÊÒÁ໚¹µíÒá˹‹§·Õ蹌Í·ÕèÊØ´

¢ŒÍ ª×Íè â¤Ã§ÊÌҧ

1

3
 21

1.3 ¡ÒÃàÃÕ¡ª×Íè ä«â¤ÅáÍÅ䤹 (Cycloalkyne) Êٵ÷ÑÇè ä» CnH2n-4 “¹íÒ˹ŒÒ´ŒÇ Cyclo ŧ·ŒÒ´ŒÇ –yne”
ª×Íè µÒÁÃкº IUPAC

- ãËŒ¾Ñ¹¸ÐÊÒÁ໚¹µíÒá˹‹§¹ŒÍ·ÕèÊØ´
- ¹íÒ˹ŒÒ´ŒÇ cyclo ŧ·ŒÒ´ŒÇ –yne

“âÁàÅ¡ØÅ·Õàè Åç¡·ÕèÊ´Ø ¢Í§ä«â¤ÅáÍÅ䤹¤Í× ä«â¤ÅÍÍ¡ä·¹ (¤ÒϺ͹ 8 ÍеÍÁ)”

¢ŒÍ ª×Íè â¤Ã§ÊÌҧ

1

2
 22

4. ¡ÒÃàÃÕ¡ª×Íè áÍâÃáÁµÔ¡ (Aromatic)

ª×Íè ÊÒÁÑÞ (Common name)

ª×Íè µÒÁÃкº IUPAC

ËÅÑ¡¡ÒÃ
1. ¡íÒ˹´ãËŒ benzene ໚¹â¤Ã§ÊÌҧËÅÑ¡
2. àÃÕ¡ª×èÍËÁÙ‹á·¹·ÕèµÒÁÅíҴѺÍÑ¡ÉÃÀÒÉÒÍѧ¡ÄɵÑÇáá¢Í§ËÁÙ‹¹Ñé¹
â´ÂÃкصíÒá˹‹§¢Í§ËÁÙ‹á·¹·Õèãˌ໚¹µÑÇàÅ¢¹ŒÍ·ÕèÊØ´

¢ŒÍ ª×Íè â¤Ã§ÊÌҧ

1

¡Ã³Õǧ Benzene ໚¹ËÁÙá‹ ·¹·Õè ãËŒàÃÕ¡ǧູ«Õ¹·Õàè »š¹ËÁÙá‹ ·¹·Õ¹è ¹Ñé Ç‹Ò ËÁÙ‹ “phenyl”

2-phenylhexane
 23

¡Ã³ÕÁËÕ ÁÙ‹á·¹·ÕÊè Ìҧ¾Ñ¹¸Ð¡ÑºÇ§àº¹«Õ¹ÁÒ¡¡Ç‹Ò 1 ËÁÙ‹

 24

5 ¡ÒÃàÃÕ¡ª×Íè áÍÅ¡ÍÎÍŏ (Alcohol ; R-OH) “ ŧ·ŒÒ´ŒÇ –ol ”

IUPAC
ª×Íè ÊÒÁÑÞ
ª×Íè µÒÁÃкº IUPAC
- àÅ×Í¡â«‹·ÕèÂÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡
- ãËŒËÁÙ‹ –OH ໚¹µíÒá˹‹§·Õ¹è ŒÍ·ÕèÊØ´
- ¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” ŧ·ŒÒ´ŒÇ “ol”

ª¹Ô´¢Í§ Alcohol
25
 26

6 ¡ÒÃàÃÕ¡ª×Íè ÍÕà·ÍÏ (Ether ; R-O-R) “ alkoxy + alkane”

ª×Íè ÊÒÁÑÞ
- Í‹Ò¹ËÁÙ‹ alkyl µÒÁµÑÇÍÑ¡Éà ŧ·ŒÒ´ŒÇ ether

ª×Íè µÒÁÃкº IUPAC

- àÅ×Í¡â«‹·ÕèÂÒÇ·ÕèÊش໚¹â«‹ËÅÑ¡ ͋ҹ໚¹ alkane
- ÃкصíÒá˹‹§ËÁÙ‹ –OR ¹Ñº¨íҹǹ C µÒÁ´ŒÇ oxy

IUPAC
ª×Íè ÊÒÁÑÞ
 27

6.1 ¡ÒÃàÃÕ¡ª×Íè ÍÕà·ÍÏǧ»´ (Cyclic Ethers ; R-O-R) “ oxa + cyclo + alkane”

7 ¡ÒÃàÃÕ¡ª×Íè áÍÅ´Õäδ (Aldehyde ; R-CHO) “ ŧ·ŒÒ´ŒÇ –al ”

ª×Íè µÒÁÃкº IUPAC
- ¹ÑºËÁÙ‹¿˜§¡ªÑ¹ (-CHO) ໚¹µíÒá˹‹§·Õè 1
- àÅ×Í¡â«‹ËÅÑ¡·ÕèÁÕËÁÙ‹¿˜§¡ªÑ¹ ¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” ŧ·ŒÒ´ŒÇ “al”
 28

8 ¡ÒÃàÃÕ¡ª×Íè ¤Õâµ¹ (Ketone ; R-CO-R) “ ŧ·ŒÒ´ŒÇ –one ”

ª×Íè µÒÁÃкº IUPAC
- ãËŒËÁÙ‹¿˜§¡ªÑ¹ (-CO-) ໚¹µíÒá˹‹§·Õ蹌Í·ÕèÊØ´
- àÅ×Í¡â«‹ËÅÑ¡·ÕèÁÕËÁÙ‹¿˜§¡ªÑ¹ ¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” ŧ·ŒÒ´ŒÇ “-one”
 29

9 ¡ÒÃàÃÕ¡ª×Íè ¡Ã´¤ÒϺ͡«ÔÅ¡Ô (Carboxylic acid ; R-COOH) “ ŧ·ŒÒ´ŒÇ –oic acid ”

ª×Íè ÊÒÁÑÞ (Common name)
- ÁÑ¡àÃÕ¡µÒÁáËÅ‹§·ÕèÁÒ Å§·ŒÒ´ŒÇ -ic acid

- ºÍ¡µíÒá˹‹§ËÁÙ‹á·¹·Õ贌Ǡα-, β-, γ-, δ-

 30

ª×Íè µÒÁÃкº IUPAC

- ãËŒËÁÙ‹¿˜§¡ªÑ¹ (-COOH) ໚¹µíÒá˹‹§·Õè 1 àÊÁÍ
- àÅ×Í¡â«‹ËÅÑ¡·ÕèÁÕËÁÙ‹¿˜§¡ªÑ¹ ¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” ŧ·ŒÒ´ŒÇ “-oic acid”

- ¶ŒÒËÁÙ‹ –COOH á·¹·Õ躹ǧ àÃÕ¡ª×èÍǧµ‹Í´ŒÇ –carboxylic acid

- ÊÒ÷ÕèÁÕËÁÙ‹ –COOH 2 ËÁÙ‹ ãˌŧ·ŒÒª×èÍ´ŒÇ –dioic acid
 31

10 ¡ÒÃàÃÕ¡ª×Íè àÍÊà·ÍÏ (Ester ; R-COO-R) “ ŧ·ŒÒ´ŒÇ –oate ”

¡ÒÃàÃÕ¡ª×Íè Alkyl + common name

(¨Ò¡ alcohol) (¨Ò¡ carboxylic acid)
Alkyl + IUPAC name
(¨Ò¡ alcohol) (¨Ò¡ carboxylic acid)
à»ÅÕÂè ¹ –ic acid ໚¹ -ate à»ÅÕÂè ¹ –oic acid ໚¹ -ate
 32

11 ¡ÒÃàÃÕ¡ª×Íè àÍÁÕ¹ (Amine ; R-NH2) “ ŧ·ŒÒ´ŒÇ –amine ”

»ÃÐàÀ·¢Í§àÍÁÕ¹

ª×Íè µÒÁÃкº IUPAC (1°-amine)

- ãËŒËÁÙ‹¿˜§¡ªÑ¹ (-NH2) ໚¹µíÒá˹‹§·Õ蹌Í·ÕèÊØ´
- àÅ×Í¡â«‹ËÅÑ¡·ÕèÁÕËÁÙ‹¿˜§¡ªÑ¹
¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” + ÃкصíÒá˹‹§ -NH2 + ŧ·ŒÒ´ŒÇ “amine”
 33

ª×Íè µÒÁÃкº IUPAC (2°-amine)

- 2°-amine àÃÕ¡ª×Íè ໚¹ N-alkyl + alkanamine

ª×Íè µÒÁÃкº IUPAC (3°-amine)

- 3°-amine àÃÕ¡ª×Íè ໚¹ N,N-dialkyl + alkanamine

ËÃ×Í N-alkyl-N-alkyl + alkanamine

Aromatic amine
 34

12 ¡ÒÃàÃÕ¡ª×Íè àÍäÁ´ (Amide ; R-CO-NH2) “ ŧ·ŒÒ´ŒÇ –amide ”

»ÃÐàÀ·¢Í§àÍäÁ´

ª×Íè µÒÁÃкº IUPAC (1°-amide)

- ãËŒËÁÙ‹¿˜§¡ªÑ¹ (-CONH2) ໚¹µíÒá˹‹§·Õè 1 àÊÁÍ
- àÅ×Í¡â«‹ËÅÑ¡·ÕèÁÕËÁÙ‹¿˜§¡ªÑ¹
¹Ñº¨íҹǹ C ͋ҹ໚¹ alkane µÑ´ “e” + ŧ·ŒÒ´ŒÇ “amide”

ª×Íè µÒÁÃкº IUPAC (2°-amide)

- 2°-amide àÃÕ¡ª×Íè ໚¹ N-alkyl + alkanamide
 35

ª×Íè µÒÁÃкº IUPAC (3°-amide)

- 3°-amide àÃÕ¡ª×Íè ໚¹ N,N-dialkyl + alkanamide

Aromatic amide
 36

ËÑÇ¢ŒÍ·Õè 5. äÍâ«àÁÍÏ (Isomer)

1 äÍâ«àÁÍÏâ¤Ã§ÊÌҧ (Structural Isomer)

ËÁÒ¶֧ ÊÒ÷ÕèÁÕÊÙµÃâÁàÅ¡ØÅàËÁ×͹¡Ñ¹ ᵋÁÕÊÙµÃâ¤Ã§ÊÌҧµ‹Ò§¡Ñ¹
â¤Ã§ÊÌҧ¢Í§ÊÒûÃСͺ ¨Ø´ËÅÍÁàËÅÇ ( ¨Ø´à´×Í´ ( ¤ÇÒÁ˹Òṋ¹·Õè 20OC (g/cm3)
O O
C) C)
CH3–CH2– CH2– CH3 – 138.3 – 0.5 0.573
CH3
– 159.4 – 11.7 0.551
CH3 CH CH3
¡ÒþԨÒóÒÇ‹ÒÊÒäÙË‹ ¹Ö§è ໚¹äÍâ«àÁÍÏ¡¹Ñ ËÃ×ÍäÁ‹
1. ¶ŒÒ»ÃСͺ´ŒÇ¸ҵص‹Ò§ª¹Ô´¡Ñ¹ ¨ÐäÁ‹à»š¹äÍâ«àÁÍÏ¡¹Ñ
2. ¶ŒÒ»ÃСͺ´ŒÇ¸ҵت¹Ô´à´ÕÂǡѹ áÅШíҹǹÍеÍÁ෋ҡѹ ¨ÐµŒÍ§¾Ô¨ÒóҢÑé¹µ‹Íä»
¡) ¶ŒÒÊÙµÃâ¤Ã§ÊÌҧàËÁ×͹¡Ñ¹ ¨Ð໚¹ÊÒê¹Ô´à´ÕÂǡѹ äÁ‹à»š¹äÍâ«àÁÍϡѹ ઋ¹
H H H H H

H C C C C C H
H H H H H H

1 2
H H H H
H C C C C C C H
H C H
H H H H H H
H

H H
H
H C H H C H
H C H
H H
H H H

3 4
H C C C C H
H C C C C H
H H H H
H H H
H C H

H
 37

¢) ¶ŒÒÊÙµÃâ¤Ã§ÊÌҧµ‹Ò§¡Ñ¹ ¨Ð໚¹äÍâ«àÁÍÏ¡¹Ñ ઋ¹ ÊÒ÷ÕèÁÕÊÙµÃâÁàÅ¡ØÅ໚¹ C5H12 ÁÕ 3 äÍâ«àÁÍÏ ´Ñ§¹Õé

CH3
CH3
CH3 C CH3
CH3 CH2 CH2 CH2 CH3
CH3 CH CH2 CH3
CH3

ÊÒûÃСͺÍÔ¹·ÃՏ㹢ŒÍã´µ‹Í仹Õé໚¹äÍâ«àÁÍÏ¡¹Ñ

1. (CH3CH2)2CHCH3 ¡Ñº CH3CH2C(CH3)3

....................................................................................................................................
2. ¡Ñº
....................................................................................................................................
CH3 CH CH2 CH3
3. CH3COOCH3 ¡Ñº
OH
.................................................... ...............................................................................
4. CH3OCH3 ¡Ñº CH3CH2OH
....................................................................................................................................
5. CH3(CH2)2 HO ¡Ñº (CH3CH2)2CO
....................................................................................................................................
6. CH2=CHCH(CH3)2 ¡Ñº (CH3)2CHCH=CH2
....................................................................................................................................
7. CH3(CH2)3CHO ¡Ñº (CH3CH2)2CO
....................................................................................................................................
8. (CH3)3N ¡Ñº CH3NHCH2CH3
....................................................................................................................................
9. (CH3)2CCl2 ¡Ñº (CH3)2CHCH2Cl
....................................................................................................................................
OH
10. ¡Ñº HO OH

OH
....................................................................................................................................
Cl CH3 Cl

11. H3C C CH2 CH3 ¡Ñº H2C C CH3

Cl Cl
....................................................................................................................................
 38

1.1 äÍâ«àÁÍÏÊÒÂâ«‹¤ÒϺ͹
ËÅÑ¡¡ÒÃà¢Õ¹äÍâ«àÁÍÏ
1. ¾Ô¨ÒóҨҡÊÙµÃâÁàÅ¡ØÅ¡‹Í¹Ç‹Ò໚¹ÊÒûÃÐàÀ·ã´
2. àÁ×èÍ·ÃҺNjÒ໚¹ÊÒûÃÐàÀ·ã´áŌǨ֧¹íÒÁÒà¢Õ¹äÍâ«àÁÍÏ
3. ¶ŒÒ໚¹ÊÒþǡ⫋ແ´ (Open chain ËÃ×Í Acyclic) ÁÑ¡¨ÐàÃÔèÁà¢Õ¹äÍâ«àÁÍϨҡµÑÇ·ÕÁè Õ C µ‹Í¡Ñ¹
໚¹ÊÒµçÂÒÇ·ÕèÊØ´¡‹Í¹ ËÅѧ¨Ò¡¹Ñ鹨֧Ŵ¤ÇÒÁÂÒǢͧ C ÊÒµçŧ¤ÃÑé§ÅÐÍеÍÁ
4. 㹡óշÕè໚¹äÎâ´Ã¤ÒϺ͹Ẻǧ (Cyclic chain) ÁÑ¡¨ÐàÃÔèÁ¨Ò¡Ç§·ÕèàÅç¡¡‹Í¹ ¤×ÍàÃÔèÁ¨Ò¡ C 3
ÍеÍÁ áŌǨ֧à¾ÔèÁ໚¹ 4 ÍеÍÁ µÒÁÅíҴѺ
µÑÇÍ‹ҧ
ÊÒ÷ÕèÁÕÊÙµÃâÁàÅ¡ØÅ໚¹ C5H10 ÁÕäÍâ«àÁÍÏ·Õè໚¹

- ⫋ແ´ 5 äÍâ«àÁÍÏ (â«‹µÃ§ 2 äÍâ«àÁÍÏ áÅÐâ«‹¡Ôè§ 3 äÍâ«àÁÍÏ )

- â«‹»´ 1 äÍâ«àÁÍÏ

H H H H H H H H H
H

1 C C C C C H 2 H C C C C C H
H
H H H H H H

H
H
H C H
H C H H H
H
3 H
H H
4 C C C C H
C C C C H
H
H H H
H H

H H
H
H C H
H C H H C C H

5 H H H 6 C C
H H
H C C C C H H H

H H
 39

ÊÙµÃâÁàÅ¡ØÅ äÍâ«àÁÍÏ
C3H8

C4H10

C5H12

C6H14

C7H16

C8H18
 40

ÊÙµÃâÁàÅ¡ØÅ äÍâ«àÁÍÏ
C3H6

C4H8

C5H10

C6H12
 41

1.2 äÍâ«àÁÍϵÒí á˹‹§¢Í§ËÁÙ‹¿§˜ ¡ª¹Ñ (Positional Isomer)

äÍâ«àÁÍÏ·Õèà¡Ô´¨Ò¡ËÁÙ‹¿˜§¡ª¹Ñ ÁÒà¡ÒСѺÍеÍÁ¢Í§¤ÒϺ͹ã¹â¤Ã§ÊÌҧËÅÑ¡·ÕèµíÒá˹‹§µ‹Ò§¡Ñ¹

1.3 äÍâ«àÁÍϪ¹Ô´¢Í§ËÁÙ¿‹ ˜§¡ª¹Ñ (Functional Isomer)

äÍâ«àÁÍÏ·ÕèÁÕËÁÙ¿‹ ˜§¡ªÑ¹µ‹Ò§¡Ñ¹ ÊÙµÃâÁàÅ¡ØÅàËÁ×͹¡Ñ¹áµ‹ÊÙµÃâ¤Ã§ÊÌҧµ‹Ò§¡Ñ¹

2 äÍâ«àÁÍÏÊàµÍÃÔâÍ (Stereo Isomer)

ÊÙµÃâÁàÅ¡ØÅàËÁ×͹¡Ñ¹ ÊÙµÃâ¤Ã§ÊÌҧàËÁ×͹¡Ñ¹ ÍеÍÁµ‹Íã¹ÅѡɳÐà´ÕÂǡѹ ᵋ¡ÒèѴàÃÕ§ÍеÍÁã¹·ÕèÇ‹Ò§ã¹
ÊÒÁÁÔµÔµÒ‹ §¡Ñ¹
2.1 äÍâ«àÁÍÏàâҤ³Ôµ (Geometric isomer)
໚¹äÍâ«àÁÍϢͧÊÒûÃСͺ·Õèà¡Ô´¨Ò¡ ÍеÍÁ ËÃ×Í ¡ÅØ‹ÁÍеÍÁ ·ÕèÁÒà¡ÒеçµíÒá˹‹§¾Ñ¹¸Ð¤Ù‹ / ÁØÁ¢Í§
â¤Ã§ÊÌҧ·Õè໚¹Ç§ ÁÕ¡ÒèѴàÃÕ§µÑÇẺ 3 ÁÔµÔ áµ¡µ‹Ò§¡Ñ¹ ẋ§Í͡໚¹ 2 Ẻ
äÍâ«àÁÍÏẺ«ÔÊ (cis–)ÍеÍÁ/¡ÅØ‹ÁÍеÍÁ·Õè äÍâ«àÁÍÏẺ·Ãҹʏ (trans–)
àËÁ×͹¡Ñ¹¨Ñ´ÍÂÙ‹´ŒÒ¹à´ÕÂǡѹ ÍеÍÁ/¡ÅØ‹ÁÍеÍÁ·ÕèàËÁ×͹¡Ñ¹¨Ñ´ÍÂÙ‹µíÒá˹‹§
µÃ§¢ŒÒÁ¡Ñ¹

¨Ø´ËÅÍÁàËÅÇ –138.9OC ¨Ø´à´×Í´ 3.7OC ¨Ø´ËÅÍÁàËÅÇ –105.5OC ¨Ø´à´×Í´ 0.8OC

â¤Ã§ÊÌҧ·ÕèäÁ‹ÁÕäÍâ«àÁÍÏẺ«ÔÊËÃ×Í·Ãҹʏ
- ÁÕËÁÙ‹á·¹·ÕèàËÁ×͹¡Ñ¹ ≥ 2 ËÁÙ‹ º¹ C à´ÕÂǡѹ
 42

1. ÊÒûÃСͺÍÔ¹·ÃՏ㹢ŒÍã´à»š¹äÍâ«àÁÍϡѹ
H H
H C Cl Cl C H
¡ H ¡Ñº H ............................................

H H H Cl
¢ Cl C C Cl ¡Ñº Cl C C H ............................................
Cl H H Cl

H H H
H H H H H C C C H
¤ H C C C C H ¡Ñº H H ............................................
H H H H H C H
H

H H H H H H
H C O C C H H C C O C H
§ H H H ¡Ñº H H H ...........................................

O H H O
¨ H C O C H ¡Ñº H C C O H ............................................
H H

© H CH2CH3 ¡Ñº H3C CH3 ............................................

C C C C
H H H H

ª H3C CH3 ¡Ñº H3C Cl ............................................

C C C C
Cl Cl Cl CH3
2. áÍŤչ·Õè¡íÒ˹´ãËŒµ‹Í仹ÕéÁÕ«ÔÊ–·ÃҹʏäÍâ«àÁÍÏËÃ×ÍäÁ‹ ¶ŒÒÁÕãËŒÃкØÇ‹Òâ¤Ã§ÊÌҧã´à»š¹áºº«ÔÊËÃ×Í·Ãҹʏ
H3C CH2CH3 H CH2CH3

¡ ¢
H H ……………………. H CH3 …………......................
H CH3

µ §
CH3CH2 H ………………………. ………………………………..

¨ ………………..……… © ………...……………
 43

ÍÕ-«Õ äÍâ«àÁÍÏ (E-Z isomer)

ËÒ isomer 㹡óշÕèÁÕËÁÙ‹·ÕèÁÒà¡ÒеçµíÒá˹‹§¾Ñ¹¸Ð¤Ù‹ äÁ‹àËÁ×͹¡Ñ¹
ÁÕ geometrical isomer ᵋäÁ‹ãª‹ cis, trans ¨Ð㪌Ãкº E, Z
E áÅÐ Z ໚¹ÈѾ·à©¾ÒТͧ isomers ·Ò§àâҤ³Ôµ
- E ÁÒ¨Ò¡¤íÒÇ‹Ò entgegen (ËÁÒ¶֧ opposite, µÃ§¢ŒÒÁ)
- Z ÁÒ¨Ò¡¤íÒÇ‹Ò Zusamman (á»ÅÇ‹Ò together, ã¹´ŒÒ¹à´ÕÂǡѹ)
㪌 ‘ Sequence rule ’ ¡®¡ÒèѴÅíҴѺ
¡ÒôÙÍ¹Ñ ´Ñº
1. ÍеÍÁ·ÕèÁÕàÅ¢ÍеÍÁÊÙ§¡Ç‹Ò¨ÐÁÕÅíҴѺ·ÕèÊÙ§¡Ç‹Ò໚¹ High = H
2. ÍеÍÁ·ÕÁè ÕàÅ¢ÍеÍÁÊÙ§¡Ç‹Ò¨ÐÁÕÅíҴѺ·ÕèµèíÒ¡Ç‹Ò໚¹ Low = L
3. ¶ŒÒàÅ¢ÍеÍÁ෋ҡѹ ãËŒ¾Ô¨ÒóÒÍеÍÁ¶Ñ´ä»
4. ¶ŒÒÍеÍÁÊÌҧ¾Ñ¹¸Ð¤Ù‹ËÃ×;ѹ¸ÐÊÒÁ ãËŒ¾Ô¨ÒóÒÇ‹ÒÍеÍÁ¹Ñé¹µ‹Í¡ÑºÍеÍÁÍ×è¹à»š¹ 2 ËÃ×Í 3 ÍеÍÁ
¶ŒÒËÁÙ·‹ ÁÕè ÍÕ ¹Ñ ´ÑºÊÙ§¡Ç‹ÒÍÂÙ‹¢ÒŒ §à´ÕÂǡѹ : Z
¶ŒÒËÁÙ·‹ ÁÕè ÍÕ ¹Ñ ´ÑºÊÙ§¡Ç‹ÒÍÂÙ¤‹ ¹ÅТŒÒ§¡Ñ¹ : E

Cis-trans ËÃ×Í E-Z ???

 44

2.2 äÍâ«àÁÍÏàªÔ§áʧ (optical isomer)

ÊÒ÷ÕèÁÕÊÙµÃâÁàÅ¡ØÅáÅÐÊÙµÃâ¤Ã§ÊÌҧàËÁ×͹¡Ñ¹
ᵋÁÕ¡ÒÃËÁعÃйҺáʧâ¾ÅÒäÃʏ (plane polarized light) ᵡµ‹Ò§¡Ñ¹
«Ö觨Ðà¡Ô´¡ÑºâÁàÅ¡ØÅ·ÕèÁÕ ä¤ÃÑŤÒϺ͹ (chiral carbon)

chiral carbon achiral carbon

äÍâ«àÁÍÏàªÔ§áʧ ẋ§à»š¹ 2 ª¹Ô´ 䴌ᡋ
1. ÍÔá¹¹ªÔâÍàÁÍÏ (Enantiomer)
2. ä´áÍÊÊàµÍÃÔâÍàÁÍÏ (Diastereomer)
1. ÍÔá¹¹ªÔâÍàÁÍÏ (Enantiomer)
໚¹âÁàÅ¡ØÅ·ÕèÁÕâ¤Ã§ÊÌҧ໚¹ÀҾ㹡ÃШ¡à§Ò ·Õ諌͹·Ñº¡Ñ¹äÁ‹Ê¹Ô·
 45

2. ä´áÍÊÊàµÍÃÔâÍàÁÍÏ (Diastereomer) ÍÒ¨àÃÕÂ¡Ç‹Ò ä´ÍÐÊàµÍÃÔâÍàÁÍÏ

໚¹âÁàÅ¡ØÅ·ÕèäÁ‹à»š¹ÀҾ㹡ÃШ¡à§Ò áÅÐÁÕ ä¤ÃÑŤÒϺ͹ > 1 ÍеÍÁ

(I) (II) (III) (IV)

ÊÒ÷Õàè »š¹ Diastereomer ¡Ñ¹ä´Œá¡‹

¤Ù‹ Enantiomer 䴌ᡋ

¤Ù‹ diasteriomer
 46

ËÑÇ¢ŒÍ·Õè 6. ÊÁºÑµÔ¢Í§ÊÒûÃСͺÍÔ¹·ÃՏ
6.1 ÊÁºÑµ¢Ô ͧÊÒûÃСͺäÎâ´Ã¤ÒϺ͹
ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹ 䴌ᡋ
ÊÁºÑµ·Ô Ò§¡ÒÂÀÒ¾
1. ໚¹âÁàÅ¡ØÅäÁ‹ÁÕ¢ÑéÇ äÁ‹ÅÐÅÒ¹éíÒ ¤ÇÒÁ˹Òṋ¹¹ŒÍ¡NjҹéíÒ áçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØÅ໚¹áç
Å͹´Í¹
2. ¨Ø´à´×Í´¨Ø´ËÅÍÁàËÅǵèíÒ ¨Ðà¾ÔèÁ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¢Í§¤ÒϺ͹·Õèà¾ÔèÁ¢Öé¹
3. ·ÕèÍسËÀÙÁÔˌͧ (25OC)
C 1-4 ÍеÍÁ ÁÕʶҹÐ໚¹á¡Ê
C 5–17 ÍеÍÁ ໚¹¢Í§àËÅÇ
C 18 ÍеÍÁ¢Ö¹é ä»à»š¹¢Í§á¢ç§
4. ໚¹ÊÒûÃСͺ·ÕèäÁ‹ÁÕÊÕ äÁ‹ÁÕ¡ÅÔè¹ àÁ×è͹íÒÁÒ㪌໚¹àª×éÍà¾ÅÔ§µŒÍ§àµÔÁÊÒ÷ÕèÁÕ¡ÅÔè¹Å§ä» ઋ¹ butyl
mercaptan à¾×è͵ÃǨÊͺ¡ÒÃÃÑèǢͧᡍÊ
5. â¤Ã§ÊÌҧ·Õè໚¹â«‹µÃ§¨ÐÁըشà´×Í´ÊÙ§¡Ç‹Òâ«‹¡Ôè§ à¹×èͧ¨Ò¡¤ÇÒÁ˹Òṋ¹ÁÒ¡¡Ç‹Ò
¨§à»ÃÕºà·Õº¨Ø´à´×Í´¢Í§ÊÒõ‹Í仹Õé
CH3
CH3CH2CH CH2CH3
¡. CH3CH2CH2CH2CH3 ¢. ¤. H3C C CH3
CH3
CH3

ÊÁºÑµ·Ô Ò§à¤Áբͧ Alkane

1. ¡ÒÃà¼ÒäËÁŒ ÊÒûÃСͺáÍÅहÊÒÁÒöÅØ¡äËÁŒ´Õ äÁ‹ÁàÕ ¢Á‹ÒáÅФÇѹ àÁ×èÍà·Õº¡ÑºäÎâ´Ã¤ÒϺ͹ª¹Ô´Í×è¹·ÕèÁÕ
¨íҹǹÍеÍÁ¤ÒϺ͹෋ҡѹ ઋ¹
2 C4H10(g) + 13 O2(g) 
→ 8 CO2(g) + 10 H2O(g)

C6H12(g) + 9 O2(g) → 6 CO2(g) + 6 H2O(g)



¨§à¢Õ¹ÊÁ¡ÒÃáÊ´§¡ÒÃà¼ÒäËÁŒÍ‹ҧÊÁºÙó¢Í§ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹µ‹Í仹Õé
1. ÍÕà·¹

2. ä«â¤ÅºÔÇà·¹

´ØÅÊÁ¡ÒáÒÃà¼ÒäËÁŒ¢Í§àλ෹ â´Â¡ÒÃàµÔÁàÅ¢ÊÑÁ»ÃÐÊÔ·¸Ôì㹪‹Í§Ç‹Ò§ »ÃÔÁҳᡍÊÍÍ¡«ÔਹÁռŵ‹Í»ÃÔÁÒ³¡ÒÃ

à¡Ô´à¢Á‹ÒÍ‹ҧäÃ
 47

2. »¯Ô¡ÃÔ ÔÂÒ¡ÒÃá·¹·Õè (Substitution reaction) áÍÅह໚¹ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹ÍÔèÁµÑÇ «Öè§ËÁÒ¶֧Áվѹ¸Ð

ÃÐËÇ‹Ò§ÍеÍÁ¤ÒϺ͹໚¹¾Ñ¹¸Ðà´ÕèÂÇ ÊÒÁÒöà¡Ô´»¯Ô¡ÔÃÔÂҡѺáÎâÅਹ (halogen : F , Cl , Br , I) ä´Œã¹
·ÕÁè ÕáʧÊÇ‹Ò§ â´ÂÍеÍÁ¢Í§àÎâÅਹ¨Ðá·¹·ÕèÍеÍÁ¢Í§äÎâ´Ãਹ 1 ÍеÍÁ äÎâ´Ãਹ·Õè¶Ù¡á·¹·Õè¨ÐÃÇÁ¡Ñº
áÎâÅਹà¡Ô´à»š¹á¡ÊäÎâ´ÃਹàÎäÅ´ (HX àÁ×èÍ x á·¹¸ÒµØáÎâÅਹ ) «Öè§à»š¹á¡Ê·ÕèÁÕÊÁºÑµÔ໚¹¡Ã´

H H H H H H
H H H H H H
H C C C C C C H
H C C C C C C H + Br2 light
  → H H H H H Br
+ HBr
H H H H H H

hexane Bromohexane hydrogenbromide

»¯Ô¡ÔÃÔÂҡѺÊÒÃÅÐÅÒÂâºÃÁÕ¹ àÃÕ¡NjÒâºÃÁÕ๪ѹ (Bromination) ¨Ñ´à»š¹»¯Ô¡ÃÔ ÂÔ Ò·ÕèÊíÒ¤ÑޢͧáÍÅह à¾ÃÒÐ㪌

·´ÊͺáÍÅह䴌 ¶ŒÒ¿Í¡¨Ò§ÊÕâºÃÁչ䴌㹷ÕèÊÇ‹Ò§ áÊ´§Ç‹Ò໚¹áÍÅह
¨§à¢Õ¹â¤Ã§ÊÌҧÅÔÇÍÔʢͧ¼ÅÔµÀѳ±·Õèà¡Ô´¨Ò¡»¯Ô¡ÔÃÔÂÒá·¹·Õè¢Í§¤ÅÍÃչ㹷ÕèÊÇ‹Ò§¡ÑºÊÒûÃСͺÍÔ¹·ÃՏµ‹Í仹Õé

light
1. C6H14 + Br2   →

+ Br2 light
  →
2.
»ÃÐ⪹¢Í§áÍÅह
1. CH4 ÁÕà·¹ >> àª×éÍà¾ÅÔ§ã¹âç俿‡Ò , âç§Ò¹ , Çѵ¶Ø´Ôºã¹¡ÒüÅÔµàÁ·Ò¹ÍÅ (CH3OH)
2. ÍÕà·¹ (C2H6) ¼ÅÔµàÍ·ÔÅÕ¹ (C2H4) áÅÐâ¾Ãྐྵ (C3H8) ¼ÅÔµâ¾Ã¾ÔÅÕ¹ (C3H6) >> ÊÒõÑ駵Œ¹ã¹¡ÒüÅÔµ
àÁç´¾ÅÒʵԡ
3. ᡍʼÊÁÃÐËÇ‹Ò§â¾Ãྐྵ (C3H8) ¡ÑººÔÇà·¹ (C4H10) 㪌໚¹á¡Êàª×éÍà¾ÅÔ§ËاµŒÁ àÁ×èͺÃèØ㹶ѧàËÅç¡ÀÒÂ㵌
¤ÇÒÁ´Ñ¹ÊÙ§ ¨ÐÁÕʶҹÐ໚¹¢Í§àËÅÇ ¨Ö§àÃÕÂ¡Ç‹Ò “ᡍʻâµÃàÅÕÂÁàËÅÇ” (Liquefied Petroleum Gas ËÃ×Í LPG)
4. àΡૹ 㪌໚¹µÑÇ·íÒÅÐÅÒÂã¹ÍصÊÒË¡ÃÃÁ¡ÒÃÊ¡Ñ´¹éíÒÁѹ¾×ª áÅйéíÒËÍÁ
5. ä«â¤ÅàΡૹ >> µÑÇ·íÒÅÐÅÒÂ㹡Ò÷íÒàëԹáÅÐáÅ¡à¡ÍÏ 㪌ŌҧÊÕ à»š¹ÊÒõÑ駵Œ¹ã¹¡ÒüÅÔµÊÒûÃСͺ
ÍÔ¹·ÃՏ ઋ¹ ູ«Õ¹
6. áÍÅह·ÕèÁÕÁÇÅâÁàÅ¡ØÅÊÙ§æ ઋ¹ ¾ÒÃÒ¿¹ 㪌à¤Å×ͺ¼Ñ¡áÅмÅäÁŒà¾×èÍÃÑ¡ÉÒ¤ÇÒÁªØ‹Áª×é¹áÅÐÂѺÂÑ駡ÒÃà¨ÃÔÞàµÔºâµ
¢Í§àª×éÍÃÒ ¹Í¡¨Ò¡¹Õé Âѧ㪌áÍÅह໚¹ÊÒõÑ駵Œ¹ã¹ÍصÊÒË¡ÃÃÁËÅÒª¹Ô´ ઋ¹ ÍصÊÒË¡ÃÃÁ¼ÅÔµ¼§«Ñ¡¿Í¡
àÊŒ¹ã ÊÒÃà¤ÁÕ·Ò§¡ÒÃà¡ÉµÃ áÅÐÊÒáíҨѴÈѵÃپת
â·É¢Í§áÍÅह
- áÍÅह໚¹âÁàÅ¡ØÅäÁ‹ÁÕ¢ÑéÇ ¨Ö§ÅÐÅÒÂÊÒûÃСͺÍÔ¹·ÃՏ·ÕèäÁ‹ÁÕ¢ÑéÇ àª‹¹ ä¢ÁѹáÅйéíÒÁѹ ä´Œ´Õ
- ¡ÒÃÊÙ´´Áäͧ͢áÍÅह໚¹ÍѹµÃÒµ‹ÍÃкº·Ò§à´Ô¹ËÒÂ㨠â´ÂáÍÅहä»ÅÐÅÒÂä¢Áѹ㹼¹Ñ§à«Åŏ¢Í§»Í´
ËÃ×ͶŒÒ¼ÔÇ˹ѧÊÑÁ¼ÑʡѺµÑÇ·íÒÅÐÅÒ ઋ¹ àΡૹ ¨Ð·íÒãËŒ¼ÔÇ˹ѧáËŒ§áÅÐᵡ à¾ÃÒÐä¢Áѹ¶Ù¡ªÐŌҧÍÍ¡ä»
 48

ÊÁºÑµ·Ô Ò§à¤Áբͧ Alkene

1. »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒ áÍŤչµÔ´ä¿ä´Œ§‹Ò ¨Ðà¡Ô´à¢Á‹ÒËÃ×ÍÁÕ¤Çѹ ઋ¹
C2H4(g) + 3 O2(g) → 2 CO2(g) + 2 H2O(g)
¨§à¢Õ¹ÊÁ¡ÒÃáÊ´§»¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒÍ‹ҧÊÁºÙó
1. C3H6
2. C5H10

2. »¯Ô¡ÃÔ ÂÔ ÒÃÇÁµÑÇËÃ×Í»¯Ô¡ÃÔ ÂÔ Ò¡ÒÃàµÔÁ (Addition reaction) / ÃÇÁµÑÇ

áÍŤչÊÒÁÒöà¡Ô´»¯Ô¡ÃÔ ÂÔ Ò¡ÒÃàµÔÁä´Œ§Ò‹ µçºÃÔàdz¾Ñ¹¸Ð¤Ù‹ ÁÕ¤ÇÒÁNjͧäÇ㹡ÒÃà¡Ô´»¯Ô¡ÔÃÔÂÒÁÒ¡¡Ç‹ÒáÍÅह

1) »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃàµÔÁáÎâÅਹ (Addition of Halogen) ໚¹»¯Ô¡ÔÃÔÂÒ¡ÒÃàµÔÁ·Õè Cl2 ËÃ×Í Br2 ÊÒÁÒöÃÇÁµÑÇ

â´ÂµÃ§¡ÑºáÍŤչµÃ§¾Ñ¹¸Ð¤Ù‹â´ÂäÁ‹µŒÍ§ÁÕµÑÇà˧»¯Ô¡ÔÃÔÂÒ ËÃ×ÍäÁ‹µŒÍ§ãªŒáʧÊÇ‹Ò§ ¶ŒÒÃÇÁ¡Ñº Cl2 àÃÕ¡NjÒ
Chlorination ¶ŒÒÃÇÁ¡Ñº Br2 àÃÕÂ¡Ç‹Ò Bromination »¯Ô¡ÔÃÔÂÒ·Õèà¡Ô´¢Ö鹨ÐäÁ‹ÁÕᡍÊäÎâ´ÃਹàÎäÅ´ (Hydrogen
halide : HX) à¡Ô´¢Öé¹ àª‹¹
H H H H

C C C C H + Br2 
→
H H H

1–butene 1,2–dibromo butane

»¯Ô¡ÔÃÔÂÒ¹Õé໚¹»¯Ô¡ÃÔ ÔÂÒ·ÕèÊíÒ¤ÑޢͧáÍŤչ â´Â੾Òл¯Ô¡ÔÃÔÂÒ Bromination à¹×èͧ¨Ò¡ÊÒÁÒö㪌ºÍ¡¤ÇÒÁ
ᵡµ‹Ò§ÃÐËÇ‹Ò§áÍŤչ¡ÑºáÍÅह䴌 â´Â·ÑèÇä»ãªŒÊÒÃÅÐÅÒ Br2 ã¹ CCl4 (Br2/CCl4)
• áÍŤչ ¨Ð·íÒ»¯Ô¡ÔÃÔÂÒ¿Í¡¨Ò§Êբͧ¢Í§ Br2/CCl4 ·Ñé§ã¹·ÕèÁ×´áÅзÕèÊÇ‹Ò§ â´ÂäÁ‹Áտͧᡍʢͧ HBr à¡Ô´¢Öé¹
Ex.1 ¨§à¢Õ¹ÊÁ¡ÒÃáÊ´§»¯Ô¡ÃÔ ÔÂÒÃÐËÇ‹Ò§ÊÒõ‹Í仹Õé

CH3CH2C CH2 + Cl2

CH3

Ex.2 X , Y , Z ໚¹ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹ àÁ×èÍÊÒà X áÅÐ Y ·íÒ»¯Ô¡ÔÃÔÂҡѺÊÒÃÅÐÅÒÂâºÃÁÕ¹

áÅÐÊÒà Z ·íÒ»¯Ô¡ÔÃÔÂҡѺÍÍ¡«Ôਹ¨Ðà¡Ô´»¯Ô¡ÔÃÔÂҴѧÊÁ¡ÒÃ

X + Br2 
→ C4H9Br + HBr ……….. (1)
Y + Br2 →
 C4H8Br2 ……….. (2)
Z + 9 O2 →
 6 H2O + 6 CO2 ……….. (3)

ÊÙµÃâÁàÅ¡ØŢͧ X ¤×Í_____________¢Í§ Y ¤×Í_____________áÅТͧ Z ¤×Í _________________

 49

2) »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃàµÔÁäÎâ´Ãਹ (Addition of Hydrogen) ໚¹»¯Ô¡ÔÃÔÂÒ¡ÒÃàµÔÁ H2 ËÃ×ÍàÃÕÂ¡Ç‹Ò hydrogenation

áÍŤչ¨ÐÃÇÁµÑǡѺ H2 䴌໚¹áÍÅह â´ÂÁÕ Pt , Ni ËÃ×Í Pd ໚¹µÑÇà˧»¯Ô¡ÔÃÂÔ Ò

H H H H H H H H

C C C C H + H2 
→ H C C C C H

H H H H H H H
1–butene butane

CH3CH=CHCH3 + H2 →

(CH3)2C=CH2 + H2 →

3) Hydroxylation ËÃ×Í Glycol formation áÍŤչÊÒÁÒö¿Í¡¨Ò§ÊÕËÃ×Í·íÒ»¯Ô¡ÔÃÂÔ Ò¡ÑºÊÒÃÅÐÅÒ KMnO4 ã¹

ÊÒÃÅÐÅÒ¡ô ä´Œ¼ÅÔµÀѳ±à»š¹ä¡Å¤ÍÅ (glycol) áÅÐÁյС͹ÊÕ¹éíÒµÒÅ´íҢͧáÁ§¡Ò¹ÕÊ (IV) ÍÍ¡ä«´à¡Ô´¢Ö¹é
(ä¡Å¤ÍÅ໚¹ÊÒûÃСͺ»ÃÐàÀ·áÍÅ¡ÍÎÍŏ·ÕèÁÕËÁÙ‹ –OH à¡ÒÐÍÂÙ¡‹ Ѻ C 2 ÍеÍÁµÔ´¡Ñ¹)

H H H H
H H H H
C C C C H
H C C C C H
H H H + KMnO4 + H2O → OH OH H H
+ MnO2 + KOH
glycol
1 – butene

CH3CH=CHCH3 + KMnO4 + H2O →

(CH3)2C=CH2 + KMnO4 + H2O →

ÊÁºÑµáÔ Åл¯Ô¡ÃÔ ÂÔ Ò¢Í§ä«â¤ÅáÍŤչ

ä«â¤ÅáÍŤչ ÁÕÊÁºÑµÔµ‹Ò§æ ¤ÅŒÒ¡ѺáÍŤչ ઋ¹ ¡ÒÃÅØ¡äËÁŒ ¡ÒÃà¡Ô´»¯Ô¡ÔÃÂÔ ÒẺàµÔÁËÃ×ÍÃÇÁµÑǡѺàÎâÅਹ
ઋ¹ ¿Í¡¨Ò§ÊÕâºÃÁÕ¹ à¡Ô´»¯Ô¡ÔÃÔÂҡѺÊÒÃÅÐÅÒÂâ¾á·Êà«ÕÂÁà»ÍÏáÁ§¡Ò๵
Br
+ Br2 
→
Br
ไซโคลเฮกซีน ไดโบรโมไซโคลเฮกเซน
 50
H2
C
H2C CH2

HC CH + Br2 
→

H2
C
H2C CH2

HC CH + KMnO4 + H2O 
→

»ÃÐ⪹ªÍ§áÍŤչ
1. ÍÕ·Õ¹áÅÐâ¾Ã¾Õ¹ (C2H4 áÅÐ C3H6) ª×èÍÊÒÁÑÞ¤×ÍàÍ·ÔÅÕ¹áÅÐâ¾Ã¾ÔÅÕ¹ µÒÁÅíҴѺ 㪌໚¹ÊÒõÑ駵Œ¹ã¹¡ÒüÅÔµ
¾ÍÅÔàÁÍÏ»ÃÐàÀ·¾ÍÅÔàÍ·ÔÅÕ¹áÅоÍÅÔâ¾Ã¾ÔÅÕ¹ µÒÁÅíҴѺ
2. áÍŤչºÒ§ª¹Ô´ãªŒà»š¹ÊÒûÃاᵋ§¡ÅÔè¹ÍÒËÒà ઋ¹ ÅÔâÁ¹Õ¹ «Öè§ãËŒ¡ÅÔè¹ÁйÒÇ
3. 㪌áÍŤչ໚¹ÊÒõÑ駵Œ¹ã¹¡ÒÃã¹ÍصÊÒË¡ÃÃÁ¼ÅÔµàÍ·Ò¹ÍÅ ¾ÅÒʵԡ áÅÐÊÒëѡ¿Í¡
àÁ×èÍà»ÃÕº¡ÑºáÍÅह áÍŤչ áÅÐáÍÅ䤹 ·ÕèÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹෋ҡѹ ¨ÐÁըشà´×Í´–¨Ø´
ËÅÍÁàËÅÇàÃÕ§ÅíҴѺ´Ñ§¹Õé
áÍÅ䤹 > áÍÅह > áÍŤչ
¨§àÃÕ§ÅíҴѺ¨Ø´à´×Í´¨Ò¡ÁÒ¡ä»ËÒ¹ŒÍÂ
C5H10 C5H12 C5H8

ÊÁºÑµ·Ô Ò§à¤Áբͧ Alkyne

1. »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒ (Combusion) ¡ÒÃà¼ÒäËÁŒã¹ºÃÃÂÒ¡ÒÈ»¡µÔ ¨ÐãËŒà¢Á‹ÒÁÒ¡¡Ç‹ÒáÍŤչ
¨§à¢Õ¹ÊÁ¡ÒÃáÊ´§»¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒÍ‹ҧÊÁºÙó

1. C3H4

2. C4H6

2. »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃàµÔÁ (Addition reaction) áÍÅ䤹à»š¹ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹äÁ‹ÍÔèÁµÑÇ ¨Ö§à¡Ô´»¯Ô¡ÔÃÔÂÒ¡ÒÃ

àµÔÁáÎâÅਹ
1) »¯Ô¡ÔÃÔÂÒ¡ÒÃàµÔÁàÎâÅਹ áÍÅ䤹¿Í¡¨Ò§ÊÕÊÒÃÅÐÅÒÂâºÃÁչ䴌 â´ÂäÁ‹µŒÍ§ãªŒµÑÇà˧»¯Ô¡ÔÃÔÂÒËÃ×Í
áʧÊÇ‹Ò§
Br Br

Br 2 Br 2
R C C R → → R C C R

Br Br
 51

2) »¯Ô¡ÔÃÔÂÒ¡ÒÃàµÔÁäÎâ´Ãਹ ËÃ×Í hydrogenation áÍÅ䤹ÊÒÁÒöà¡Ô´»¯Ô¡ÔÃÔÂҡѺäÎâ´Ãਹâ´ÂÁÕ

Pt , Ni , Pd ໚¹µÑÇà˧»¯Ô¡ÔÃÔÂÒä´ŒáÍŤչáÅÐáÍÅहµÒÁÅíҴѺ
H H


→ H2
R C C R
H2

→ R C C R

H H

CH3C≡CCH2CH3 + 2Br2 →

CH3(CH2)2C≡CH + 2H2 →

3. »¯Ô¡ÔÃÔÂÒ¿Í¡¨Ò§ÊÕ KMnO4 »¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§áÍÅ䤹¡Ñº KMnO4 ¾ºÇ‹Òã¹âÁàÅ¡ØÅ·ÕèÁÕµíÒá˹‹§¢Í§

¾Ñ¹¸ÐÊÒÁµ‹Ò§¡Ñ¹ ¼ÅÔµÀѳ±·Õèà¡Ô´¢Ö鹨е‹Ò§¡Ñ¹´ŒÇÂ
1. ¶ŒÒáÍÅ䤹·ÕèÁվѹ¸ÐÊÒÁÍÂÙ‹·ÕèµÃ§ C µíÒá˹‹§·Õè 1 àÁ×èÍà¡Ô´»¯Ô¡ÔÃÔÂÒáŌǨÐà¢Õ¹ÊÁ¡ÒÃä´Œ´Ñ§¹Õé

2. áÍÅ䤹·ÕèÁվѹ¸ÐÊÒÁÍÂÙ‹µÃ§ C µíÒá˹‹§·Õè 2 ໚¹µŒ¹ä» àÁ×èÍà¡Ô´»¯Ô¡ÃÔ ÔÂÒáŌǨÐà¢Õ¹ÊÁ¡ÒÃä´Œ´Ñ§¹Õé

3CH3C≡CCH2CH3 + 4 KMnO4 + 2 H2O →

3CH3(CH2)2C≡CH + 8 KMnO4 + 4 H2O →

 52

»ÃÐ⪹¢Í§áÍÅ䤹
1. áÍÅ䤹·ÕèÃÙŒ¨Ñ¡¡Ñ¹·ÑèÇ令×ÍÍÕä·¹ (ethyne) ª×èÍÊÒÁÑÞ¤×ÍÍÐà«·ÔÅÕ¹ (C2H2) àµÃÕÂÁä´Œ¨Ò¡»¯Ô¡ÔÃÔÂÒ
ÃÐËÇ‹Ò§á¤Åà«ÕÂÁ¤ÒÏ亴·íÒ»¯Ô¡ÔÃÔÂҡѺ¹éíÒ
CaC2(s) + 2 H2O(l) Ca(OH)2(aq) + C2H2(g)

→

2. ã¹·Ò§ÍصÊÒË¡ÃÃÁÊÒÁÒöàµÃÕÂÁ C2H2 ä´Œ¨Ò¡ CH4 â´ÂãËŒ¤ÇÒÁÌ͹ÊÙ§æ ã¹àÇÅÒ·ÕèÊÑé¹ÁÒ¡æ

1500 o C , 0 . 01 −0 . 1 s
2CH4(g)       → C2H2(g) + 2 H2(g)
3. ᡍʼÊÁÃÐËÇ‹Ò§ C2H2 ¡Ñº O2 ã¹ÍѵÃÒʋǹ·ÕèàËÁÒÐÊÁàÃÕÂ¡Ç‹Ò oxy-acetylene ãËŒà»ÅÇä¿·ÕèÌ͹ÊÙ§
¶Ö§ 3000OC ã¹àª×èÍÁâÅËÐáÅеѴâÅËÐä´Œ ¹Í¡¨Ò¡¹Õé C2H2 Âѧ㪌໚¹á¡Êàª×éÍà¾ÅÔ§·ÕèãËŒáʧÊÇ‹Ò§ à˧¡ÒÃÍÍ¡´Í¡
¢Í§¾×ª áÅÐà˧¡ÒÃÊØ¡¢Í§¼ÅäÁŒãËŒàÃçÇ¢Öé¹
ÊÁºÑµ·Ô Ò§à¤Áբͧ Aromatic
1. »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒ ÍÐâÃÁÒµÔ¡äÎâ´Ã¤ÒϺ͹µÔ´ä¿ãËŒà¢Á‹ÒáÅФÇѹÁÒ¡ 䴌ᡍʤÒϺ͹ä´ÍÍ¡ä«´
áÅÐä͹éíҴѧÊÁ¡ÒÃ
2 C6H6(l) + 15 O2(g) → 12 CO2(g) + 6 H2O(g)
ÅíҴѺà¢Á‹Ò ÍÐâÃÁÒµÔ¡ > áÍÅ䤹 > áÍŤչ > áÍÅह
2. »¯Ô¡ÃÔ ÂÔ Òá·¹·Õè
1) »¯Ô¡ÔÃÔÂÒá·¹·Õè´ŒÇÂàÎâÅਹ (Halogenation) ູ«Õ¹¨Ð·íÒ»¯Ô¡ÔÃÔÂҡѺ Cl2 ËÃ×Í Br2 â´ÂÁÕ¼§àËÅç¡
ËÃ×Í FeCl3 ໚¹µÑÇà˧»¯Ô¡ÃÔ ÔÂÒ à¡Ô´»¯Ô¡ÔÃÔÂÒá·¹·Õè䴌ᡍÊäÎâ´ÃਹàÎäÅ´ ઋ¹
2 C6H6(l) + 15 O2(g) →
 12 CO2(g) + 6 H2O(g)
Cl

+ Cl2 →
 + HCl

Chloro Hydrogen
benzene benzene chloride
 53

ÊÃØ» ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹
·´Êͺ´ŒÇ Br2/CCl4 ·´Êͺ´ŒÇÂ
ª¹Ô´ à¢Á‹Ò
ã¹·ÕÁè ´× ã¹·ÕèÊÇ‹Ò§ KMnO4
Alkane    (HBr(g)) 
Alkene    
Alkyne    
Aromatic   * 
* + ¼§ Fe(s) ÊÒÁÒöà¡Ô´»¯Ô¡ÔÃÔÂÒ¡ÒÃá·¹·Õèä´Œ (HBr(g))
¨Ø´à´×Í´
1. ¨íҹǹ C à¾ÔèÁ¢Öé¹ ¨Ø´à´×Í´à¾ÔèÁ¢Öé¹
2. ¨íҹǹ C ෋ҡѹ â¤Ã§ÊÌҧµ‹Ò§¡Ñ¹ : â«‹µÃ§ > â«‹¡Ôè§ (¨Ø´à´×ʹŴŧàÁ×èÍ¡Ôè§ÁÒ¡¢Öé¹)
3. Alkyne > Alkane > Alkene
 54

6.2 ÊÁºÑµ¢Ô ͧÊÒûÃСͺÍÔ¹·ÃÕ· ÕèÁ¸Õ ÒµØÍÍ¡«Ôਹ໚¹Í§¤»ÃСͺ

ÊÒûÃСͺÍÔ¹·ÃÕ· ÕèÁ¸Õ ÒµØÍÍ¡«Ôਹ໚¹Í§¤»ÃСͺ 䴌ᡋ

ÊÁºÑµ¢Ô ͧ Alcohol
ÊÁºÑµ·Ô Ò§¡ÒÂÀÒ¾
àÁ×èÍáÍÅ¡ÍÎÍŏÅÐÅÒ¹éíÒ ËÁÙ‹ –OH ã¹áÍÅ¡ÍÎÍŏ¨ÐäÁ‹áµ¡µÑÇ໚¹
äδÃÍ¡ä«´ÚäÍÍ͹ (OH–) à¹×èͧ¨Ò¡¾Ñ¹¸ÐÃÐËÇ‹Ò§ËÁÙ‹ –OH ¡ÑºËÁÙ‹áÍŤÔÅã¹
áÍÅ¡ÍÎÍŏ໚¹¾Ñ¹¸Ðâ¤àÇàŹµ ʋǹ·ÕèäÁ‹ÁÕ¢ÑéÇ Ê‹Ç¹·ÕèÁÕ¢ÑéÇ
X ÊÙµÃâ¤Ã§ÊÌҧ ¨Ø´à´×Í´ (OC) ÊÀÒ¾ÅÐÅÒÂ䴌㹹éíÒ·Õè
20 OC (g/ ¹éíÒ 100 g)
àÁ·Ò¹ÍÅ CH3OH 64.6 ÅÐÅÒÂä´Œ´Õ
àÍ·Ò¹ÍÅ CH3CH2OH 78.2 ÅÐÅÒÂä´Œ´Õ
â¾Ã¾Ò¹ÍÅ CH3CH2CH2OH 97.2 ÅÐÅÒÂä´Œ´Õ
ºÔÇ·Ò¹ÍÅ CH3CH2CH2CH2OH 117.7 7.9
ྐྵ·Ò¹ÍÅ CH3CH2CH2CH2CH2OH 137.9 2.3
1. ¨Ø´à´×Í´ ¨Ø´à´×Í´¢Í§áÍÅ¡ÍÎÍŏ¨Ðà¾ÔèÁ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¤ÒϺ͹·Õèà¾ÔèÁ¢Öé¹ ÁÇÅâÁàÅ¡ØÅÁÕ¤‹ÒÊÙ§¢Öé¹
áçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØŨ֧ÊÙ§¢Öé¹´ŒÇ à¹×èͧ¨Ò¡áÍÅ¡ÍÎÍŏ໚¹âÁàÅ¡ØÅÁÕ¢ÑéÇ ¨Ö§ÁÕ·Ñé§áçÅ͹´Í¹áÅÐáç´Ö§´Ù´
ÃÐËÇ‹Ò§¢ÑéÇ à»š¹áçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØÅ ¹Í¡¨Ò¡¹ÕéËÁÙ‹ –OH ÊÒÁÒöà¡Ô´¾Ñ¹¸ÐäÎâ´ÃਹÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§
âÁàÅ¡ØŢͧáÍÅ¡ÍÎÍŏ䴌
R
H
O
O R
R H
O H
H
H O
O R
O H
R
R O H

R
¡ÒÃà¡Ô´¾Ñ¹¸ÐäÎâ´ÃਹÃÐËÇ‹Ò§âÁàÅ¡ØŢͧáÍÅ¡ÍÎÍŏ
áÍÅ¡ÍÎÍŏ¨Ö§Áըشà´×Í´ÊÙ§¡Ç‹ÒáÍÅह·ÕèÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹෋ҡѹ à¹×èͧ¨Ò¡áÍÅह໚¹âÁàÅ¡ØÅ
äÁ‹ÁÕ¢ÑéÇ ¨Ö§ÁÕ੾ÒÐáçÅ͹´Í¹à·‹Ò¹Ñé¹
2. ¡ÒÃÅÐÅÒ¹éÒí áÍÅ¡ÍÎÍŏ·ÕèâÁàÅ¡ØÅÁÕ C 1–3 ÍеÍÁ ÅÐÅÒ¹éíÒä´Œ´Õ à¹×Íè §¨Ò¡áÍÅ¡ÍÎÍŏÁÕËÁÙ‹ –OH
«Öè§à»š¹Ê‹Ç¹·ÕèÁÕ¢ÑéÇã¹âÁàÅ¡ØÅáÅÐà¡Ô´¾Ñ¹¸ÐäÎâ´Ãਹ¡Ñº¹éíÒä´Œ ¨Ö§·íÒãËŒáÍÅ¡ÍÎÍŏÅÐÅÒ¹éíÒ áµ‹àÁ×èÍÁÕ¨íҹǹÍеÍÁ
C ÁÒ¡¢Öé¹ ¨ÐÅÐÅÒ¹éíÒä´Œ¹ŒÍÂŧ
 55

ÊÁºÑµ·Ô Ò§à¤ÁÕ
1. »¯Ô¡ÃÔ ÂÔ Ò¡ÒÃà¼ÒäËÁŒ áÍÅ¡ÍÎÍŏÊÒÁÒöµÔ´ä¿ä´Œ´Õ äÁ‹ÁÕà¢Á‹ÒáÅФÇѹ ä´Œ¼ÅÔµÀѳ±à»š¹á¡Ê
¤ÒϺ͹ä´ÍÍ¡ä«´áÅйéíÒ à»š¹»¯Ô¡ÔÃÂÔ Ò¤Ò¾Åѧ§Ò¹ ´Ñ§ÊÁ¡ÒÃ
CH3CH2OH(l) + 3 O2(g) → 2 CO2(g) + 3 H2O(g)
2. »¯Ô¡ÃÔ ÂÔ Ò¡ÑºâÅËзÕÇè Í‹ §äÇ áÍÅ¡ÍÎÍŏäÁ‹à¡Ô´»¯Ô¡ÔÃÂÔ Ò¡Ñº NaHCO3 ¨Ö§äÁ‹áÊ´§ÊÁºÑµÔ໚¹¡Ã´ ᵋ
ÊÒÁÒöà¡Ô´»¯Ô¡ÔÃÔÂҡѺâÅËзÕèNjͧäÇ (Active metal) ઋ¹ Na â´ÂâÅËШÐࢌÒä»á·¹·ÕèÍеÍÁ¢Í§ H ã¹ËÁÙ‹ –OH
¨Ð䴌ᡍÊäÎâ´Ãਹ ´Ñ§ÊÁ¡ÒÃ

2 CH3CH2–OH(l) + 2 Na(g) 
→ 2 CH3CH2–ONa(l) + H2(g)
Sodium ethoxide
¨§à¢Õ¹ÊÁ¡ÒÃáÊ´§»¯Ô¡ÃÔ ÂÔ ÒÃÐËÇ‹Ò§ÊÒõ‹Í仹Õé
CH3CH2CH2CH2OH + O2 →
CH3CH2 CH CH2OH + Na →
CH3
ÊÁºÑµáÔ Åл¯Ô¡ÃÔ ÂÔ Ò¢Í§áÍÅ¡ÍÎÍŏºÒ§ª¹Ô´
1. àÁ·Ò¹ÍÅ (Methanol) ໚¹áÍÅ¡ÍÎÍŏ·ÕèÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹¹ŒÍ·ÕèÊØ´ àµÃÕÂÁä´Œ¨Ò¡¡ÒÃà¼ÒäÁŒ·Õè
ÍسËÀÙÁÔʧ٠ã¹ÀÒÇзÕè»ÃÒȨҡÍÒ¡ÒÈ ã¹ÍصÊÒË¡ÃÃÁàµÃÕÂÁä´Œ¨Ò¡»¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§¤ÒϺ͹Á͹͡䫴¡ÑºäÎâ´Ãਹ
ÀÒÂ㵌ÍسËÀÙÁÔáÅФÇÒÁ´Ñ¹ÊÙ§ â´ÂÁÕâÅËÐÍÍ¡ä«´ ઋ¹ Fe2O3 , ZnO / Cr2O3 ໚¹µÑÇà˧»¯Ô¡ÔÃÔÂÒ ´Ñ§ÊÁ¡ÒÃ

300 - 400oC , 200 atm

CO + H2 CH3OH
ต◌ั
วเร◌่
งปฏ◌ิ
ก◌ิ
ร◌ิ
ยา
ตัวเรงปฏิกิริยา

àÁ·Ò¹ÍÅ໚¹¾Ôɵ‹ÍËҧ¡Ò ¶ŒÒࢌÒÊًËҧ¡Ò¨ж١ÍÍ¡«Ôä´Ê¡ÅÒÂ໚¹¿ÍÏÁÒÅ´Õäδ (HCHO) «Ö觨зíÒãËŒ

à¡Ô´ÍÒ¡ÒûǴÈÕÃÉÐ µÒºÍ´ ËÃ×Í໚¹ÍѹµÃÒ¶֧ªÕÇÔµ
»ÃÐ⪹¢Í§àÁ·Ò¹ÍÅ ¹íÒÁÒ㪌໚¹µÑÇ·íÒÅÐÅÒÂÍÔ¹·ÃՏ ໚¹àª×éÍà¾ÅÔ§ ໚¹ÊÒõÑ駵Œ¹ã¹¡ÒüÅÔµ¾ÅÒʵԡ
ÂÒ áÅÐÊÒûÃСͺÍÔ¹·ÃՏª¹Ô´Í×è¹ àª‹¹ ¿ÍÏÁÒÅ´Õäδ
2. àÍ·Ò¹ÍÅ (ethanol) ໚¹áÍÅ¡ÍÎÍŏÍÕ¡ª¹Ô´Ë¹Ö觷չè íÒÁÒ㪌»ÃÐ⪹ àµÃÕÂÁä¡Œ¨Ò¡¡ÒÃËÁÑ¡¹éíÒµÒÅ·Õèä´Œ
¨Ò¡¼ÅäÁŒ ËÃ×Íệ§¨Ò¡¸Ñ޾ת㹷Õè»ÃÒȨҡÍÍ¡«Ôਹ à͹ä«Á¨Ò¡ÂÕʵËÃ×ÍᤷÕàÃÕ ¨Ðª‹ÇÂà˧»¯Ô¡ÔÃÔÂÒ ´Ñ§ÊÁ¡ÒÃ

C6H12O6 + ÂÕʵ → 2 CH3CH2OH + 2 CO2

àÍ·Ò¹ÍÅ·Õèä´Œ¨Ò¡ËÁÑ¡¹éíÒµÒšѺÂÕʵ¹Õé㪌ºÃÔâÀ¤ã¹ÃÙ»¢Í§äǹ àºÕÂÏ áÅÐàËÅŒÒ ¶ŒÒᵋºÃÔâÀ¤ÁÒ¡ æ ¨Ð

à¡Ô´ÍѹµÃÒµ‹ÍËҧ¡Ò µÑº áÅÐà¡Ô´¡ÒÃàʾµÔ´
 56

ã¹·Ò§ÍصÊÒË¡ÃÃÁàµÃÕÂÁàÍ·Ò¹ÍÅä´Œ¨Ò¡»¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§ÍÕ·Õ¹¡Ñº¹éíÒ ÀÒÂ㵌ÍسËÀÙÁÔáÅФÇÒÁ´Ñ¹ÊÙ§
â´ÂÁաôࢌÁ¢Œ¹à»š¹¤ÑÇà˧»¯Ô¡ÔÃÔÂÒ ´Ñ§ÊÁ¡ÒÃ

300 oC , 200 atm

CH2 = CH2 + H2O CH3CH2OH
H2SO4

»ÃÐ⪹¢Í§àÍ·Ò¹ÍÅ
1) 㪌໚¹µÑÇ·íÒÅÐÅÒÂ㹡ÒüÅÔµ¹éíÒËÍÁáÅÐÂÒ
2) 㪌໚¹ÊÒæ‹Òàª×éÍâä
3) àÍ·Ò¹ÍżÊÁ¡Ñº¹éíÒÁѹູ«Ô¹ÍÍ¡à·¹ 91 ã¹ÍѵÃÒʋǹàÍ·Ò¹ÍÅ 1 ʋǹ ¡Ñº¹éíÒÁѹູ«Ô¹ 9 ʋǹ
໚¹¹éíÒÁѹᡍÊâ«ÎÍŏ
4) ໚¹ÊÒõÑ駵Œ¹ã¹¡ÒüÅÔµÊÕÂŒÍÁ ÂÒ à¤Ã×èͧÊíÒÍÒ§ áÅÐ㪌¼ÅÔµÊÒûÃСͺÍÔ¹·ÃՏª¹Ô´Í×è¹ àª‹¹
¡Ã´áÍ«ÕµÔ¡ (CH3COOH)
ÊÁºÑµ¢Ô ͧ Ether
1. ໚¹âÁàÅ¡ØÅäÁ‹ÁÕ¢ÑéÇ äÁ‹ÅÐÅÒ¹éíÒ µÔ´ä¿ä´Œ§‹ÒÂ
2. ¨Ø´ËÅÍÁàËÅÇ ¨Ø´à´×Í´µèíÒ
3. ¤ÇÒÁ˹Òṋ¹¹ŒÍ¡NjҹéíÒ
»ÃÐ⪹¢Í§ÍÕà·ÍÏ
1. 㪌໚¹µÑÇ·íÒÅÐÅÒÂÊÒÃÍÔ¹·ÃՏ
2. ã¹Í´ÕµãªŒàÍ·Í¡«ÕÍÕà·¹ (CH3CH2OCH2CH3) ໚¹ÂÒÊź «Ö觹ÔÂÁàÃÕ¡ÊÒùÕéÇ‹ÒÍÕà·ÍÏ â´ÂÊÒùÕé¨Ð
ÍÍ¡Ä·¸Ô¡ì ´»ÃÐÊҷʋǹ¡ÅÒ§¨¹·íÒãËŒËÁ´ÊµÔ
3. 㪌àÍ·Í¡«ÕÍÕà·¹ (CH3CH2OCH2CH3) ໚¹µÑÇ·íÒÅÐÅÒÂÊÒÃã¹ËŒÍ§»¯ÔºÑµÔ¡ÒÃáÅÐã¹ÍصÊÒË¡ÃÃÁ
à¹×èͧ¨Ò¡ÍÕà·ÍÏÊÒÁÒöÅÐÅÒÂÊÒûÃСͺÍÔ¹·ÃՏ䴌ËÅÒª¹Ô´ à¡Ô´»¯Ô¡ÔÃÔÂҡѺÊÒÃÍ×è¹ä´ŒÂÒ¡ áÅÐá¡ÍÍ¡ä´Œ§‹ÒÂ
àÁ×èÍÊÔé¹ÊØ´»¯Ô¡ÔÃÔÂÒà¹×èͧ¨Ò¡ÍÕà·ÍÏÁըشà´×Í´µèíÒ
ÊÁºÑµ¢Ô ͧ Aldehyde
¨Ø´à´×Í´áÅÐÊÀÒ¾ÅÐÅÒÂä´Œ·Õè 20OC ¢Í§áÍÅ´ÕäδºÒ§ª¹Ô´
¨Ø´à´×Í´ ÊÀÒ¾ÅÐÅÒÂä´Œ·Õè 20OC
ª×èÍ ÊÙµÃâ¤Ã§ÊÌҧ
(OC) (g / ¹éíÒ 100 g)
àÁ·Ò¹ÒÅ HCHO – 19.1 ÅÐÅÒÂä´Œ´Õ
àÍ·Ò¹ÒÅ CH3CHO 20.1 ÅÐÅÒÂä´Œ´Õ
â¾Ã¾Ò¹ÒÅ CH3CH2CHO 48.0 16
ºÔÇ·Ò¹ÒÅ CH3CH2CH2CHO 74.8 7
ྐྵ·Ò¹ÒÅ CH3CH2CH2CH2CHO 103.0 ÅÐÅÒÂä´Œ¹ŒÍÂ
 57

1. - ໚¹âÁàÅ¡ØÅÁÕ¢ÑéÇ
- áÍÅ´Õä䏷ÕèÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹¹ŒÍÂæ ÅÐÅÒ¹éíÒä´Œ´Õ
- áçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØÅ໚¹áç´Ö§´Ù´ÃÐËÇ‹Ò§¢ÑéÇ áµ‹ÊÒÁÒöà¡Ô´¾Ñ¹¸ÐäÎâ´Ãਹ¡ÑºâÁàÅ¡ØÅ
¢Í§¹éíÒä´Œâ´Âà¡Ô´ÊÅѺ¡ÑºâÁàÅ¡ØŢͧ¹éíÒ (Associated hydrogen bond)
2. ¨Ø´à´×Í´¢Í§áÍÅ´ÕäδÁÕá¹Ç⹌Áà¾ÔÁè ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¤ÒϺ͹·Õèà¾ÔèÁ
»ÃÐ⪹¢Í§áÍÅ´Õäδ
1. áÍÅ´Õä䏷Õ辺㹸ÃÃÁªÒµÔʋǹãËދ໚¹¹éíÒÁѹËÍÁÃÐàËÂ
CH3 O O
O
H H

HO ÇйÔÅÔ¹ «Ô¹¹ÒÁÒÅ´Õäδ
2. áÍÅ´Õä䏷Õè㪌ã¹Ç§¡ÒÃÈÖ¡ÉÒ ä´Œá¡‹ àÁ·Ò¹ÒÅ (HCHO) ÁÕª×èÍÊÒÁÑÞÇ‹Ò ¿ÍÏÁÒÅ´Õäδ
(formaldehyde) ÁÕʶҹÐ໚¹á¡Ê·ÕèÍسËÀÙÁÔˌͧ ÁÕ¡ÅÔ蹩ع ÅÐÅÒ¹éíÒä´Œ´Õ ÊÒÃÅÐÅÒ¿ÍÏÁÒÅ´Õäδà¢ŒÁ¢Œ¹ 40%
àÃÕ¡NjÒÊÒÃÅÐÅÒ¿ÍÏÁÒÅÔ¹ (formalin) 㪌´Í§ÊѵǏà¾×èÍäÁ‹ãˌ๋Òໄ͛  㪌໚¹ÊÒõÑ駵Œ¹ã¹ÍصÊÒË¡ÃÃÁ¾ÍÅÔàÁÍÏ
ÊíÒËÃѺ¼ÅÔµÊÔè§·Í ©¹Ç¹ ¾ÃÁ ÇÑÊ´Ø·Õè㪌᷹äÁŒ áÅÐ㪌໚¹µÑÇ·íÒÅÐÅÒ¾ÅÒʵԡ ¿ÍÏÁÒÅÔ¹ÁÕ¾ÔÉ ·íÒãËŒÃФÒÂà¤×ͧ
µÒ ¨ÁÙ¡ ¼ÔÇ˹ѧ »Ç´ÈÕÃÉÐáÅÐÁÖ¹§§ä´Œ
3. ã¹ÍصÊÒË¡ÃÃÁàµÃÕÂÁ¿ÍÏÁÒÅ´Õäδä´Œ¨Ò¡»¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§àÁ·Ò¹ÍšѺÍÍ¡«ÔਹÀÒÂ㵌ͳ Ø ËÀÙÁÔÊÙ§
â´ÂÁÕâÅËÐà§Ô¹à»š¹µÑÇà˧»¯Ô¡ÔÃÔÂÒ ´Ñ§ÊÁ¡ÒÃ

600 oC
2 CH3OH(g) + O2(g) 2 HCHO + 2 H2O(g)
Ag

ÊÁºÑµ¢Ô ͧ Ketone
ÊÁºÑµ¢Ô ͧ¤Õâµ¹
1. âÁàÅ¡ØÅàÅç¡ æ ÅÐÅÒ¹éíÒä´Œ àÁ×èͨíҹǹÍеÍÁ¤ÒϺ͹à¾ÔèÁ¢Ö鹨ÐÅÐÅÒ¹éíÒä´Œ¹ŒÍÂŧ
¨Ø´à´×Í´áÅÐÊÀÒ¾ÅÐÅÒÂä´Œ·Õè 20OC ¢Í§¤Õâµ¹ºÒ§ª¹Ô´
O ÊÀÒ¾ÅÐÅÒÂä´Œ·Õè 20OC
ÊÙµÃâ¤Ã§ÊÌҧ ª×èÍ ¨Ø´à´×Í´ ( C)
(g / ¹éíÒ 100 g)
CH3COCH3 â¾Ã¾Òâ¹¹ 56.1 ÅÐÅÒÂ
CH3COCH2CH3 ºÔÇ·Òâ¹¹ 79.6 26.0
CH3COCH2CH2CH3 ྐྵ·Òâ¹¹ 102.3 6.3
CH3COCH2CH2CH2CH3 àΡ«Òâ¹¹ 127.2 2.0

2. ¨Ø´à´×Í´à¾ÔèÁ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¤ÒϺ͹à¹×Íè §¨Ò¡ÁÇÅâÁàÅ¡ØÅà¾ÔèÁ¢Öé¹ áçáǹà´ÍÏÇÒÅʏá¢ç§áç¢Öé¹

3. àÁ×èÍà»ÃÕºà·Õº¨Ø´à´×Í´¢Í§áÍÅह áÍÅ´Õäδ ¤Õâµ¹ áÅÐáÍÅ¡ÍÎÍŏ ·ÕèÁÕÁÇÅâÁàÅ¡ØÅã¡ÅŒà¤Õ§¡Ñ¹
¾ºÇ‹Ò¨Ø´à´×Í´¨ÐàÃÕ§ÅíҴѺ´Ñ§¹Õé áÍÅ¡ÍÎÍŏ > ¤Õâµ¹ > áÍÅ´Õäδ >ÍÕà·ÍÏ > áÍÅह
 58

»ÃÐ⪹¢Í§¤Õâµ¹
1. ¤Õâµ¹·Õè㪌ÁÒ¡ 䴌ᡋ â¾Ã¾Òâ¹¹ (propanone : CH3COCH3) ÁÕª×èÍÊÒÁÑÞ¤×ÍáÍ«Õâµ¹ (acetone) ໚¹
¤Õâµ¹·ÕèÁÕ¨íҹǹÍеÍÁ C ¹ŒÍ·ÕèÊØ´ ໚¹¢Í§àËÅÇãÊäÁ‹ÁÕÊÕ ÁÕ¡ÅÔè¹Í‹Í¹æ ÃÐà˧‹Ò ÅÐÅÒÂã¹¹éíÒä´Œ´Õ ¨Ö§ãªŒà»š¹
µÑÇ·íÒÅÐÅÒ¾ÅÒʵԡáÅÐáÅ¡à¡ÍÏ áÍ«Õâµ¹ÊÒÁÒöÅÐÅÒÂÊÒûÃСͺÍÔ¹·ÃՏÍ×è¹æ ä´Œ´Õ áÍ«Õ⵹໚¹ÊÒ÷ÕèäÇä¿
ÁÒ¡ ¨Ö§µŒÍ§ãªŒ´ŒÇ¤ÇÒÁÃÐÁÑ´ÃÐÇѧ ¶ŒÒÊÙ´´ÁࢌÒä»ÁÒ¡æ ¨Ð·íÒãËŒÁÖ¹§§ «ÖÁ áÅÐËÁ´ÊµÔ
2. ¡ÒúÙà ¼ÅԵ䴌¨Ò¡µŒ¹¡ÒúÙà 㪌໚¹ÊÒÃäÅ‹áÁŧ ໚¹Ê‹Ç¹¼ÊÁ¢Í§ÂÒ´Á ÂÒËÁ‹Í§ áÅÐà¤Ã×èͧÊíÒÍÒ§

¡ÒúÙÃ
O

ÊÒûÃСͺÍÔ¹·ÃՏᵋÅФٵ‹ Í‹ 仹Õé ª¹Ô´ã´ÁÕ¨´Ø à´×Í´ÊÙ§¡Ç‹Ò

¡. CH3COCH3 ¡Ñº C4H10

¢. CH3CH2CHO ¡Ñº CH3CH2CH2CH2CHO

¤. CH3CH2CH2CHO ¡Ñº CH3CH2CH2CH2OH

 59

ÊÁºÑµ¢Ô ͧ Carboxylic acid

ÊÁºÑµ¢Ô ͧ¡Ã´¤ÒϺ͡«ÔÅ¡Ô
1. ¡Ã´¤ÒϺ͡«ÔÅԡ໚¹¡Ã´Í‹Í¹ ᵡµÑÇä´ŒºÒ§Ê‹Ç¹ ãËŒäÎâ´Ãà¹ÕÂÁäÍÍ͹ (H3O+) ¹ŒÍ ËÃ×ÍᵡµÑÇäÁ‹
ÊÁºÙó
CH3COOH(aq) + H2O(l) H3O+(aq) + CH3COO–(g)
Ka = [H3 O + ] [CH3 COO− ]
[CH3 COOH]

= 1.8 x 10–5
¤‹Ò¤§·Õè¡ÒÃᵡµÑǢͧ¡Ã´ (Ka) ¹ÕéÁÕ¤‹Ò¹ŒÍ áÊ´§Ç‹Ò¡Ã´áͫյԡᵡµÑÇä´Œ¹ŒÍ ËÃ×Íà¡Ô´»¯Ô¡ÔÃÔÂÒä»
¢ŒÒ§Ë¹ŒÒä´Œ¹ŒÍ áÊ´§Ç‹Ò¡Ã´áͫԵԡ໚¹¡Ã´Í‹Í¹ ¡Ã´¤ÒϺ͡«ÔÅÔ¡Í×è¹ æ ¡çÁÕÊÁºÑµÔઋ¹à´ÕÂǡѹ¹Õé
CH3COOH(aq) + NaOH(l) →
¡Ã´ àºÊ
ª×èÍ ÊÙµÃâ¤Ã§ÊÌҧ ¨Ø´à´×Í´ ÊÀÒ¾ÅÐÅÒÂ䴌㹹éíÒ·Õè 20OC
(OC) (g / ¹éíÒ 100 g)
¡Ã´àÁ·Òâ¹ÍÔ¡ HCOOH 100.8 ÅÐÅÒÂä´Œ´Õ
¡Ã´àÍ·Òâ¹ÍÔ¡ CH3COOH 117.9 ÅÐÅÒÂä´Œ´Õ
¡Ã´â¾Ã¾Òâ¹ÍÔ¡ CH3CH2COOH 140.8 ÅÐÅÒÂä´Œ´Õ
¡Ã´ºÔÇ·Òâ¹ÍÔ¡ CH3(CH2)2COOH 163.3 ÅÐÅÒÂä´Œ
¡Ã´à¾¹·Òâ¹ÍÔ¡ CH3(CH2)3COOH 185.5 3.7
¡Ã´àΡ«Òâ¹ÍÔ¡ CH3(CH2)4COOH 205.7 1.0
2. ¡Ã´¤ÒϺ͡«ÔÅÔ¡ÅÐÅÒ¹éÒí ä´Œà¹×èͧ¨Ò¡
- âÁàÅ¡ØÅÁÕÊÀÒ¾¢ÑéÇâÁàÅ¡ØÅÊÙ§ â´ÂËÁÙ‹¿˜§¡ªÑ¹·ÕèÁÕ¢ÑéÇÁÕ¶Ö§ 2 ËÁÙ‹ ¤×ÍËÁÙ‹äδÃÍ¡«ÔÅáÅÐËÁÙ‹¤ÒϺ͹ÔÅ
- ᵋÊÀÒ¾ÅÐÅÒÂä´Œ¢Í§¡Ã´¤ÒϺ͡«ÔÅÔ¡¨ÐŴŧàÁ×èͨíҹǹÍеÍÁ¤ÒϺ͹à¾ÔèÁ¢Öé¹ à¹×èͧ¨Ò¡âÁàÅ¡ØÅÁÕ
ʋǹ·ÕèäÁ‹ÁÕ¢ÑéÇÁÒ¡¢Öé¹
1. ¡Ã´¤ÒϺ͡«ÔÅԡᵋÅФًµ‹Í仹Õé ª¹Ô´ã´ÅÐÅÒ¹éíÒä´Œ´Õ¡Ç‹Ò¡Ñ¹
¡. CH3COOH ¡Ñº CH3CH2CH2COOH ………………………………
¢. COOH ¡Ñº CH3CH2COOH ………………………………
2. ¨§à¢Õ¹ÊÁ¡ÒáÒÃÅÐÅÒ¹éíҢͧ¡Ã´¤ÒϺ͡«ÔÅÔ¡µ‹Í仹Õé
¡. HCOOH

¢. CH3CH2COOH
 60

3. àÁ×èÍà»ÃÕºà·Õº¨Ø´à´×Í´¢Í§¡Ã´¤ÒϺ͡«ÔÅÔ¡¡ÑºáÍÅ¡ÍÎÍŏ·ÕèÁÕÁÇÅâÁàÅ¡ØÅã¡ÅŒà¤Õ§¡Ñ¹ ઋ¹
¡Ã´àÍ·Òâ¹ÍÔ¡ (CH3COOH) ¡Ñºâ¾Ã¾Ò¹ÍÅ (CH3H2CH2OH) ¾ºÇ‹Ò¡Ã´àÍ·Òâ¹ÍÔ¡Áըشà´×Í´ 117.9OC
ÊÙ§¡Ç‹Ò â¾Ã¾Ò¹ÍÅ·ÕèÁըشà´×Í´à¾Õ§ 97.2OC
¨Ø´à´×Í´¢Í§ ¡Ã´¤ÒϺ͡«ÔÅ¡Ô > áÍÅ¡ÍÎÍŏ
à¹×èͧ¨Ò¡ËÁÙ‹ –COOH «Öè§à»š¹ËÁÙ‹¿˜§¡ªÑ¹ã¹âÁàÅ¡ØšôÁÕÍÍ¡«Ôਹ 2 ÍеÍÁ áÅÐäÎâ´Ãਹ 1 ÍеÍÁ·Õè
ÊÒÁÒöÊÌҧ¾Ñ¹¸ÐäÎâ´Ãਹ䴌 ã¹¢³Ð·ÕèËÁÙ‹ –OH «Öè§à»š¹ËÁÙ‹¿˜§¡ªÑ¹ã¹âÁàÅ¡ØŢͧáÍÅ¡ÍÎÍŏÁÕÍÍ¡«ÔਹáÅÐ
äÎâ´ÃਹÍ‹ҧÅÐ 1 ÍеÍÁ ¾Ñ¹¸ÐäÎâ´Ãਹ·Õèà¡Ô´¢Öé¹ÃÐËÇ‹Ò§âÁàÅ¡ØŢͧ¡Ã´¤ÒϺ͡«ÔÅÔ¡¨Ö§ÁÕ¤ÇÒÁá¢ç§áçÁÒ¡¡Ç‹Ò
¢Í§áÍÅ¡ÍÎÍŏ ¡Ã´¤ÒϺ͡«ÔÅÔ¡¨Ö§ÁÕáçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØÅÁÒ¡¡Ç‹ÒáÍÅ¡ÍÎÍŏ·ÕèÁÕÁÇÅâÁàÅ¡ØÅã¡ÅŒà¤Õ§¡Ñ¹
¾Ñนธะไฮโดรเจน
พ◌ั ¹¸ÐäÎâ´Ãਹ ¾Ñ¹¸ÐäÎâ´Ãਹ
พ◌ันธะไฮโดรเจน
H R R
R C O H R R R
O R
C C H O
O O H O
O O R O
H O O
H R H H H
H O
O O R O
O C H O H R
R C O H H
R O H R O
O O H R
O C O H
R C O H R
R
¾Ñ¹¸ÐäÎâ´Ãਹ¢Í§¡Ã´¤ÒϺ͡«ÔÅ¡Ô ¾Ñ¹¸ÐäÎâ´Ãਹ¢Í§áÍÅ¡ÍÎÍŏ
3. ÊÒûÃСͺÍÔ¹·ÃՏᵋÅФًµ‹Í仹Õé ª¹Ô´ã´Áըشà´×Í´ÊÙ§¡Ç‹Ò¡Ñ¹

¡. C4H10 , CH3CH2CH2OH , CH3COOH

¢. CH3COOH , CH3CH2COOH , CH3CH2CH2COOH

¤. CH3CH2COCH3 , CH3CH2CH2CH2OH , CH3CH2COOH

»ÃÐ⪹¢Í§¡Ã´¤ÒϺ͡«ÔÅ¡Ô
1. ¾ºã¹¼ÅäÁŒ·ÕèÁÕÃÊà»ÃÕéÂÇËÅÒª¹Ô´ ઋ¹ ÊŒÁ ÁТÒÁ ÁйÒÇ

2. ໚¹Í§¤»ÃСͺ¢Í§ä¢ÁѹËÃ×͹éíÒÁѹ ઋ¹ ¡Ã´ä¢Áѹ㹾תËÃ×ÍÊѵǏ

3. ¡Ã´àÍ·Òâ¹ÍÔ¡ ËÃ×͡ôáÍ«ÕµÔ¡ (CH3COOH) ໚¹¡Ã´·Õè¤ØŒ¹à¤Â㹪ÕÇÔµ»ÃШíÒÇѹ ¡Ã´áͫյԡࢌÁ¢Œ¹

㪌໚¹µÑÇ·íÒÅÐÅÒÂ㹡ÒüÅÔµ¾ÅÒʵԡáÅÐàÊŒ¹ãÂÊѧà¤ÃÒÐˏ ¹éíÒÊŒÁÊÒªÙÁաôáÍ«ÕµÔ¡ÃŒÍÂÅÐ 4-5
 61

4. ¡Ã´àÁ·Òâ¹ÍÔ¡ (HCOOH) ÁÕª×èÍÊÒÁÑÞNjҡô¿ÍÏÁÔ¡ ໚¹¡Ã´·ÕèÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹¹ŒÍ·ÕèÊØ´

¾ºã¹¼Öé§áÅÐÁ´ ᵋʋǹãËÞ‹ä´Œ¨Ò¡¡ÒÃÊѧà¤ÃÒÐˏ 㪌໚¹ÊÒ÷Õ誋ÇÂãËŒà¹×éÍÂÒ§ã¹ÂÒ§´ÔºÃÇÁµÑǡѹ໚¹¡ŒÍ¹
㪌ã¹ÍصÊÒË¡ÃÃÁ¿Í¡Ë¹Ñ§áÅÐÍصÊÒË¡ÃÃÁÂŒÍÁ¼ŒÒ
5. ¡Ã´áÍÅ¿ÒäδÃÍ¡«Õ ËÃ×ÍàÍàͪàÍ (Alpha hydroxyl acids : AHAs) ໚¹¡Ã´¤ÒϺ͡«ÔÅÔ¡·Õèà¡Ô´ã¹
¸ÃÃÁªÒµÔ ¾ºã¹¼ÅäÁŒ ¹Á µŒ¹ÍŒÍ ÁÕËÅÒª¹Ô´ ·Õ辺º‹ÍÂ æ ¤×Í ¡Ã´áÅ¡µÔ¡ «Öè§ä´Œ¨Ò¡¹Áà»ÃÕéÂÇ ¡Ã´ä¡Åâ¤ÅÔ¡«Öè§
ä´Œ¨Ò¡µŒ¹ÍŒÍ ¡Ã´·ÒÅÔ¡«Ö§è ä´Œ¨Ò¡¼ÅáͻແŠà¡Ã» »˜¨¨ØºÑ¹ÁÕ¡ÒùíÒÁÒ AHAs ¤ÇÒÁࢌÁ¢Œ¹¹ŒÍ æ ÁÒ㪌໚¹
ʋǹ¼ÊÁ¢Í§¼ÅÔµÀѳ±ºíÒÃا¼ÔÇà¾×èÍ·íÒãËŒ¼Ôǹ؋Á äÃŒÃÔéÇÃÍ áÅЪ‹Ç»ÃѺÊÀÒ¾¼ÔÇ
O OH O O OH O

HO CH2 C OH H3C CH C OH HO C CH2 CH C OH

¡Ã´ä¡Åâ¤ÅÔ¡ ¡Ã´áÅ¡µÔ¡ ¡Ã´ÁÒÅÔ¡
ÊÁºÑµ¢Ô ͧ Ester
1. àÍÊà·ÍϨÐÁըشà´×Í´µèíÒ¡Ç‹Ò ¡Ã´¤ÒϺ͡«ÔÅÔ¡ à¹×èͧ¨Ò¡àÍÊà·ÍÏäÁ‹Áվѹ¸ÐäÎâ´ÃਹÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§
âÁàÅ¡ØÅ áçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØŨ֧¹ŒÍ¡Njҡô¤ÒϺ͡«ÔÅÔ¡
àÍÊà·ÍÏ ¡Ã´¤ÒϺ͡«ÔÅÔ¡
ÊÙµÃ
¨Ø´à´×Í´ ¨Ø´à´×Í´
âÁàÅ¡ØÅ ÊÙµÃâ¤Ã§ÊÌҧ ÊÙ µ Ãâ¤Ã§ÊÃŒ Ò §
(OC) (OC)
C2H4O2 HCOOCH3 31.7 CH3COOH 117.9
C3H6O2 HCOOCH2CH3 54.4 CH3CH2COOH 141.1
CH3COOCH3 56.9
C4H8O2 HCOOCH2CH2CH3 80.9 CH3CH2CH2COOH 163.7
CH3COOCH2CH3 77.1
CH3CH2COOCH3 79.8

2. àÁ×èÍÁÕ¨íҹǹÍеÍÁ¤ÒϺ͹à¾ÔèÁ¢Ö¹é àÍÊà·ÍϨÐÁըشà´×Í´ÊÙ§¢Öé¹
3. àÍÊà·ÍÏ·ÕèÁÕâÁàÅ¡ØÅ¢¹Ò´àÅ硨ÐÅÐÅÒ¹éíÒä´Œ ᵋÊÀÒ¾ÅÐÅÒÂä´Œ¨ÐŴŧàÁ×èͨíҹǹÍеÍÁà¾ÔèÁ¢Öé¹
àÍÊà·ÍÏ ໚¹¼ÅÔµÀѳ±·Õèà¡Ô´¨Ò¡»¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§¡Ã´¤ÒϺ͡«ÔÅÔ¡¡ÑºáÍÅ¡ÍÎÍŏ àÃÕ¡»¯Ô¡ÔÃÔÂÒ¡ÒÃ
àµÃÕÂÁàÍÊà·ÍÃÇ‹Ò “àÍÊà·ÍÃÔ¿à ¤ªÑ¹” ËÃ×Í Esterification â´ÂÁաô«ÑÅ¿ÇÃÔ¡ (H2SO4) ໚¹µÑÇà˧ ´Ñ§ÊÁ¡ÒÃ
O O
H2SO4
CH3 C OH + HO CH2CH3 CH3 C O CH2CH3 + H2O

acetic acid ethanol ethyl acetate

 62

ÊÒÁÒöà¢Õ¹ÊÁ¡Ò÷ÑèÇä»áÊ´§¡ÒÃà¡Ô´»¯Ô¡ÔÃÔÂÒàÍÊà·ÍÃÔ¿à¤ªÑ¹ä´Œ´Ñ§¹Õé

1. HCOOH + CH3OH

2. HCOOH + CH3CH2OH

3. CH3COOH + CH3OH

4. HCOOH + CH3CH2CH2OH

5. CH3COOH + CH3CH2OH

6.
»¯Ô¡ÃÔ ÂÔ Òà¤ÁբͧàÍÊà·ÍÏ
àÍÊà·ÍÏÊÒÁÒöà¡Ô´»¯Ô¡ÃÔ ÂÔ ÒäÎâ´ÃÅÔ«ÔÊ (hydolysis) «Öè§à»š¹»¯Ô¡ÔÃÔÂÒ·ÕèàÍÊà·ÍÏÊÅÒµÑÇá¡Í͡໚¹
¡Ã´¤ÒϺ͡«ÔÅÔ¡áÅÐáÍÅ¡ÍÎÍŏ (໚¹»¯Ô¡ÔÃÔÂÒŒ͹¡ÅѺ¢Í§»¯Ô¡ÔÃÔÂÒàÍÊà·ÍÃÔ¿à¤ªÑ¹) â´ÂÁաô«ÑÅ¿ÇÃԡ໚¹
µÑÇà˧»¯Ô¡ÔÃÔÂÒ·ÕèÍسËÀÙÁÔÊÙ§

(ã¹ÊÀÒÇСô)
1. HCOOCH3 + H2O

2. CH3COOCH3 + H2O

3. HCOOCH2CH2CH3 + H2O
 63

4. CH3CH2COOCH3 + H2O

5. C3H7COOCH3 + H2O

6. CH3COOCH2(CH2)6CH3 + H2O
»¯Ô¡ÔÃÔÂÒäÎâ´ÃÅÔ«ÔʢͧàÍÊà·ÍÏÊÒÁÒö à¡Ô´»¯Ô¡ÔÃÔÂÒâ´Â㪌àºÊ໚¹µÑÇà˧»¯Ô¡ÔÃÔÂÒ䴌ઋ¹¡Ñ¹ «Öè§àÃÕ¡NjÒ
»¯Ô¡ÔÃÔÂÒÊл͹¹Ô¿à¤ªÑ¹(Saponification)

à¢Õ¹ÊÁ¡ÒÃà¤ÁÕáÊ´§»¯Ô¡ÔÃÔÂÒäÎâ´ÃÅÔ«ÔʢͧàÁ·ÔÅ«ÒÅÔ«Ôàŵ·Ñé§ã¹ÀÒÇСôáÅÐàºÊ
 64

»ÃÐ⪹¢Í§àÍÊà·ÍÏ
1. àÍÊà·ÍÏ໚¹ÊÒ÷ÕèÁÕ¡ÅÔè¹ËÍÁ «Ö觾ºã¹¼ÅäÁŒËÃ×Í´Í¡äÁŒµ‹Ò§ æ «Öè§ãËŒ¡ÅÔè¹µ‹Ò§ æ ઋ¹
¡Ã´ áÍÅ¡ÍÎÍŏ àÍÊà·ÍÏ ª×èÍ ¡ÅÔè¹
CH3COOH CH3CH2OH CH3COOCH2CH3 àÍ·ÔÅàÍ·Òâ¹à͵ ¹éíÒÂÒŌҧàÅçº
CH3COOH C4H9OH CH3COOC4H9 ºÔÇ·ÔÅàÍ·Òâ¹à͵ ¡ÅŒÇÂ
CH3COOH C5H11OH CH3COOC5H11 ྐྵ·ÔÅàÍ·Òâ¹à͵ ´Í¡¹ÁáÁÇ
C3H7COOH CH3OH C3H7COOCH3 àÁ·ÔźÔÇ·Òâ¹à͵ áͻແÅ
C3H7COOH CH3CH2OH C3H7COOCH2CH3 àÍ·ÔźÔÇ·Òâ¹à͵ ÊѺ»Ðô
CH3COOH CH3(CH2)6OH CH3COOCH2(CH2)6CH3 ÍÍ¡·ÔÅàÍ·Òâ¹à͵ ÊŒÁ
O O
OH
CH3OH O CH3
àÁ·ÔÅ«ÒÅÔ«Ôàŵ ¹éíÒÁѹÃСíÒ
OH OH
O
OH
CH3COOH O C CH3
ູ«ÔÅàÍ·Òâ¹à͵ ´Í¡ÁÐÅÔ

2. ä¢ÁѹËÃ×͹éíÒÁѹ ¨Ñ´à»š¹àÍÊà·ÍÏ«Öè§à¡Ô´¨Ò¡áÍÅ¡ÍÎÍŏª×èÍ¡ÅÕà«ÍÃÍÅáÅСô¤ÒϺ͡«ÔÅÔ¡ª×è͡ôä¢Áѹ
3. àÍ·ÔÅáÍ«Õ൵ 㪌໚¹Ê‹Ç¹¼ÊÁã¹¹éíÒÂÒŌҧàÅçº áÅÐ㪌໚¹µÑÇ·íÒÅÐÅÒÂ
4. àÁ·ÔÅ«ÒÅÔ«Ôàŵ ËÃ×͹éíÒÁѹÃСíÒ ãªŒà»š¹Ê‹Ç¹¼ÊÁã¹ÂÒºÃÃà·ÒÍÒ¡ÒûǴàÁ×èÍÂ
5. àÍÊà·ÍϺҧª¹Ô´ãªŒã¹ÍصÊÒË¡ÃÃÁ¼ÅÔµàÊŒ¹ãÂÊѧà¤ÃÒÐˏ

ÊÁºÑµ¢Ô ͧ Amine
1. ¨Ø´à´×Í´à¾ÔèÁ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¤ÒϺ͹·Õèà¾ÔèÁ¢Öé¹à¹×èͧ¨Ò¡ÁÇÅâÁàÅ¡ØÅà¾ÔèÁ¢Öé¹
ÊÒà ÊÙµÃâ¤Ã§ÊÌҧ ÁÇÅâÁàÅ¡ØÅ ¨Ø´à´×Í´ (OC)
â¾Ãྐྵ CH3CH2CH3 44 – 42.1
àÍ·Ò¹ÒÁÕ¹ CH3CH2NH2 45 16.5
àÍ·Ò¹ÍÅ CH3CH2OH 46 78.2
ª×èÍ ÊÙµÃâ¤Ã§ÊÌҧ ¨Ø´à´×Í´ (OC) ÊÀÒ¾ÅÐÅÒÂ䴌㹹éíÒ·Õè 20OC (g / ¹éíÒ 100 g)
àÁ·Ò¹ÒÁÕ¹ CH3NH2 –6.3 ÅÐÅÒÂ
àÍ·Ò¹ÒÁÕ¹ CH3CH2NH2 16.5 ÅÐÅÒÂ
â¾Ã¾Ò¹ÒÁÕ¹ CH3(CH2)2NH2 47.2 ÅÐÅÒÂ
ºÔÇ·Ò¹ÒÁÕ¹ CH3(CH2)3NH2 77.0 ÅÐÅÒÂ
ྐྵ·Ò¹ÒÁÕ¹ CH3(CH2)4NH2 104.3 äÁ‹ÅÐÅÒÂ
àΡ«Ò¹ÒÁÕ¹ CH3(CH2)5NH2 132.8 äÁ‹ÅÐÅÒÂ
 65

2. àÁ×èÍà»ÃÕºà·Õº¨Ø´à´×Í´¢Í§áÍÅह àÍÁÕ¹ áÅÐáÍÅ¡ÍÎÍŏ ·ÕèÁÕÁÇÅâÁàÅ¡ØÅã¡ÅŒà¤Õ§¡Ñ¹ ¾ºÇ‹ÒàÍÁÕ¹ÁÕ

¨Ø´à´×Í´ÊÙ§¡Ç‹ÒáÍÅह ᵋµèíÒ¡Ç‹ÒáÍÅ¡ÍÎÍŏ
Alcohol > Amine > Alkane
H

R N H N H

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3. àÍÁÕ¹ÅÐÅÒÂ䴌㹹éíÒáÅеÑÇ·íÒÅÐÅÒÂÁÕ¢ÑéÇ ÊÒÃÅÐÅÒ¢ͧàÍÁչ㹹éíÒÁÕÊÁºÑµàÔ »š¹àºÊ à¹×èͧ¨Ò¡
ä¹âµÃਹÁÕÍÔàÅ硵Ã͹¤Ù‹â´´à´ÕèÂÇ«Öè§ÃѺâ»ÃµÍ¹¨Ò¡¹éíÒä´Œà¡Ô´à»š¹áÍŤÔÅáÍÁâÁà¹ÕÂÁäÍÍ͹ (alkyl ammonium
ion) [RNH3]+ áÅÐäδÃÍ¡ä«´äÍÍ͹ (OH–) ´Ñ§ÊÁ¡ÒÃ
CH3– CH2 – CH2 – NH2 + H2O [CH3– CH2 – CH2 – NH3]+ + OH–
â¾Ã¾Ò¹ÒÁÕ¹ â¾Ã¾ÔÅáÍÁâÁà¹ÕÂÁäÍÍ͹ äδÃÍ¡ä«´äÍÍ͹
àÍÁÕ¹ÁÕÊÁºÑµÔ໚¹àºÊ à¡Ô´»¯Ô¡ÔÃÔÂҡѺ¡Ã´Í¹Ô¹·ÃՏ ä´Œ¼ÅÔµÀѳ±à»š¹à¡Å×Í àª‹¹
CH3– CH2 – CH2 – CH2 – NH2 + HCl [CH3– CH2 – CH2 – CH2 – NH3]+Cl–
ºÔÇ·Ò¹ÒÁÕ¹ ºÔÇ·ÔÅáÍÁâÁà¹ÕÂÁ¤ÅÍäô
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1. àÍÁÕ¹·ÕèÁÕâÁàÅ¡ØÅ¢¹Ò´àÅç¡ ÁÕʶҹÐ໚¹á¡Ê ÅÐÅÒ¹éíÒä´Œ´Õ
2. àÍÁÕ¹ËÅÒª¹Ô´à»š¹¾ÔÉ ÁÕ¡ÅÔè¹àËÁç¹ ¡ÒÃÊÙ´´ÁàÍÁÕ¹ËÃ×ÍÍÂÙã‹ ¹ºÃÔàdz·ÕèÁÕàÍÁչࢌÁ¢Œ¹ÁÒ¡ æ ¨Ð·íÒãËŒ
à¡Ô´¡ÒÃÃФÒÂà¤×ͧµ‹Íà¹×éÍàÂ×è͵‹Ò§ æ ઋ¹ ¼ÔÇ˹ѧ áÅеÒ
3. àÍÁÕ¹ËÅÒª¹Ô´ãªŒ¼ÅÔµÊÒáíҨѴáÁŧ ÊÒáíҨѴÇѪ¾×ª ÂÒ¦‹Òàª×éÍ ÂÒ ÊÕÂŒÍÁ ʺً à¤Ã×èͧÊíÒÍÒ§µ‹Ò§ æ
4. àÍÁÕ¹·Õè໚¹ÍÑŤÒÅÍ´ ¾ºã¹Ê‹Ç¹µ‹Ò§ æ ¢Í§¾×ªºÒ§ª¹Ô´ ઋ¹ àÁÅç´ à»Å×Í¡ 㺠ÃÒ¡ ઋ¹ ÁÍÏ¿¹‚ Ê¡Ñ´
ä´Œ¨Ò¡½›¹ 㪌໚¹ÂÒºÃÃà·Ò»Ç´ ⤴ÔÍ¹Õ à»š¹ÊÒÃÊ¡Ñ´ä´Œ¨Ò¡½›¹ 㪌໚¹Ê‹Ç¹»ÃСͺã¹ÂÒá¡ŒäÍ ÁÕÄ·¸Ôì¡´»ÃÐÊÒ·
ʋǹ¡ÅÒ§ ¹Ô⤵Թ໚¹ÊÒÃàʾµÔ´·Õ辺ã¹ãºÂÒÊÙº ·íÒãËŒ¤ÇÒÁ´Ñ¹âÅËÔµáÅÐÍѵÃÒ¡ÒÃൌ¹¢Í§ËÑÇã¨à¾ÔèÁ¢Öé¹
5. àÍÁÕ¹ºÒ§ª¹Ô´¾ºã¹Ã‹Ò§¡Ò ઋ¹ ÍдÃÕ¹ÒÅÔ¹ ໚¹ÎÍÏâÁ¹·Õèà¾ÔèÁÍѵÃÒ¡ÒÃൌ¹¢Í§ËÑÇ㨠·íÒãËŒ¹éíÒµÒÅã¹
àÅ×Í´à¾ÔèÁ¢Öé¹
6. áÍÁ࿵ÒÁÕ¹ ໚¹àÍÁÕ¹Êѧà¤ÃÒÐˏ ÁÕÄ·¸Ôì¡Ãе،¹Ãкº»ÃÐÊҷʋǹ¡ÅÒ§ 㪌໚¹Ê‹Ç¹»ÃСͺã¹
à¤Ã×èͧ´×èÁºíÒÃا¡íÒÅѧ áÅÐÊÒÃàʾµÔ´·Õèª×èÍÂÒºŒÒ ÂÒÍÕ ÂÒäÍ«
OH H
HO N
CH3
NH2

HO
ÍдÃÕ¹ÒÅÔ¹ áÍÁ࿵ÒÁÕ¹

N
N CH3

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 66

ÊÁºÑµ¢Ô ͧ Amide
1. ໚¹âÁàÅ¡ØÅÁÕ¢éÇÑ áÅÐà¡Ô´¾Ñ¹¸ÐäÎâ´Ãਹ䴌
2. ¨Ø´à´×Í´ÁÕá¹Ç⹌Áà¾ÔèÁ¢Öé¹µÒÁ¨íҹǹÍеÍÁ¢Í§¤ÒϺ͹·Õèà¾ÔèÁ¢Öé¹
3. ʋǹãËÞ‹ÁÕʶҹÐ໚¹¢Í§á¢ç§·ÕèÍسËÀÙÁÔˌͧ áÅШشà´×Í´ÊÙ§¡Ç‹ÒàÍÁÕ¹·ÕèÁÕÁÇÅâÁàÅ¡ØÅã¡ÅŒà¤Õ§¡Ñ¹
O H

à¾ÃÒÐáçÂÖ´à˹ÕèÂÇÃÐËÇ‹Ò§âÁàÅ¡ØŢͧàÍäÁ´ÊÙ§¡Ç‹ÒàÍÁÕ¹ ¾Ñ¹¸ÐäÎâ´Ãਹ·Õèà¡Ô´ÃÐËÇ‹Ò§ËÁÙ‹ C ¡Ñº N

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H

H N
O R
C
C O
R H
N H
H
O N H
H N
O C
H O C
C R O
R R
N H
C
R
H N H

H
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4. àÍäÁ´·ÕèÁÕâÁàÅ¡ØÅ¢¹Ò´àÅç¡ÅÐÅÒ¹éíÒä´Œ ᵋÊÀÒ¾ÅÐÅÒÂä´Œ¨ÐŴŧÁ×èͨíҹǹÍеÍÁ¤ÒϺ͹à¾ÔÁè ¢Öé¹
¨¹¶Ö§äÁ‹ÅÐÅÒ¹éíÒ ÊÒÃÅÐÅÒ¢ͧàÍäÁ´ÁÕÊÁºÑµÔ໚¹¡ÅÒ§ à¹×èͧ¨Ò¡ÍеÍÁ¢Í§ÍÍ¡«Ôਹã¹ËÁÙ‹¤ÒϺ͹ÔÅ´Ö§´Ù´
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5. ¡ÒÃÊѧà¤ÃÒÐˏàÍäÁ´

à¢Õ¹â¤Ã§ÊÌҧ¢Í§ÊÒüÅÔµÀѳ± 2 ª¹Ô´ ·Õàè µÃÕÂÁ¨Ò¡¡Ã´¤ÒϺ͡«ÔÅ¡Ô áÅÐàÍÁչᵋÅФًµ‹Í仹Õé

¡. CH3COOH áÅÐ C6H5NH2

¢. C6H5COOH áÅÐ CH3NH2

 67

7. àÍäÁ´ÊÒÁÒöà¡Ô´»¯Ô¡ÔÃÔÂÒäÎâ´ÃÅÔ«ÔÊ ã¹ÊÒÃÅÐÅÒ¡ô ËÃ×ÍÊÒÃÅÐÅÒÂàºÊ ä´Œ¼ÅÔµÀѳ±à»š¹

¡Ã´¤ÒϺ͡«ÔÅÔ¡ áÅÐàÍÁÕ¹ ´Ñ§ÊÁ¡ÒÃ

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àÍäÁ´·Õè㪌ÁÒ¡ 䴌ᡋ ÍÐ૵ÒÁÔâ¹à¿¹ ËÃ×ÍÍÕ¡ª×èÍ˹Ö觤×;ÒÃÒ૵ÒÁÍÅ ËÃ×Íä·ÅԹ͊㪌¼ÊÁã¹ÂÒºÃÃà·Ò
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ÂÙàÃÕ ໚¹àÍäÁ´·Õ辺㹻˜ÊÊÒÇТͧÊѵǏàÅÕé§ÅÙ¡´ŒÇ¹Á ໚¹¼ÅÔµÀѳ±·Õèä´Œ¨Ò¡¡ÒÃÊÅÒÂâ»ÃµÕ¹ «Ö觻¡µÔ
¤¹¨Ð¢Ñº¶‹Ò¹ÂÙàÃÕÂÇѹÅлÃÐÁÒ³ 20–30 ¡ÃÑÁµ‹ÍÇѹ ÂÙàÃÕÂ໚¹ÊÒûÃСͺÍÔ¹·ÃՏª¹Ô´áá·ÕÊè ѧà¤ÃÒÐˏ¢Ö鹨ҡ
áÍÁâÁà¹ÕÂÁä«ÂÒ๵ «Öè§à»š¹ÊÒÃ͹Թ·ÃՏ ÂÙàÃÕÂ㪌໚¹»Ø‰Â áÅÐÇѵ¶Ø´Ôºã¹¡ÒüÅÔµ¾ÅÒʵԡ»ÃÐàÀ·¾ÍÅÔÂÙàÃÕÂ
¿ÍÏÁÒÅ´Õäδ ã¹·Ò§ÍصÊÒË¡ÃÃÁàµÃÕÂÁÂÙàÃÕÂä´Œ¨Ò¡»¯Ô¡ÔÃÔÂÒÃÐËÇ‹Ò§ CO2 ¡Ñº NH3 ´Ñ§ÊÁ¡ÒÃ
CO2 + NH3 200oC H2NCONH2 + H2O
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1. ÊÒûÃСͺÍÔ¹·ÃՏᵋÅФًµ‹Í仹Õé ÊÒÃã´¤ÇèÐÁըشà´×Í´ÊÙ§¡Ç‹Ò¡Ñ¹
O CH3 CH3

¡. ¡Ñº OH

O O
¡Ñº
¢. CH3 C O CH3 CH3 CH2 C OH

¤. CH3CH2CH2CH3 ¡Ñº CH3CH2CH2CH2OH

 68

ÊÃØ» ¡Ò÷´Êͺ·Õ¾è ºº‹ÍÂ

ª¹Ô´ Na(s) NaOH(aq) NaHCO3(aq)

Alcohol (H2(g))  
Carbaxylic acid (H2(g))  (CO2(g))
Ester   
ÊÒ÷Õàè »š¹¡Ã´ Carboxylic acid ÊÒ÷Õàè »š¹àºÊ Amine
 69

1. àÃÕ§ÅíҴѺ¨Ø´à´×Í´¨Ò¡Áҡ仹ŒÍÂ

2. ¨§ÇÒ´ÃÙ»¡Ò÷´Åͧ ¶ŒÒàµÔÁ¼§ÅÙ¡àËÁç¹¼ÊÁŧã¹ÊÒüÊÁÃÐËÇ‹Ò§¹éíÒ¡ÅÑè¹áÅÐàΡૹ
(¡íÒ˹´¤ÇÒÁ˹Òṋ¹¢Í§àΡૹ = 0.66 ¡ÃÑÁµ‹ÍÁÔÅÅÔÅÔµÃ)

ṿ·ÒÅÕ¹ (ÅÙ¡àËÁç¹)

3. àÃÕ§ÅíҴѺ¨Ø´à´×Í´¨Ò¡Áҡ仹ŒÍÂ
 70

4. ¨§ºÍ¡áçÃÐËÇ‹Ò§âÁàÅ¡ØŢͧÊÒõ‹Í仹Õé

5. à»ÃÕºà·Õº¨Ø´à´×Í´¢Í§ÊÒõ‹Í仹Õé

5.1 butan-1-ol ¡Ñº pentan-1-ol

5.2 ethanoic acid ¡Ñº methyl methanoate

5.3 hexan-1-ol ¡Ñº hexan-1-amine

6. à¢Õ¹ÊÁ¡ÒÃáÊ´§»¯Ô¡ÔÃÔÂÒà¤ÁÕÃÐËÇ‹Ò§àÁ·ÔÅູ«Õ¹ (â·ÅÙÍÕ¹) áÅÐä«â¤ÅàΡ«Õ¹ ·íÒ»¯Ô¡ÃÔ ÔÂҡѺ

ÊÒÃÅÐÅÒÂâºÃÁչ㹷ÕèÊÇ‹Ò§

1. ª×èÍ»¯Ô¡ÔÃÔÂÒ

2. ª×èÍ»¯Ô¡ÔÃÔÂÒ
 71

7. ¨§µÍº¤íÒ¶ÒÁµ‹Í仹Õé

7.1 ÊÒÃã´ÁÕâÍ¡ÒÊ໚¹ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹
7.2 ÊÒÃã´ÁÕâÍ¡ÒÊ·Õè¨Ð·íÒ»¯Ô¡ÔÃÔÂҡѺÊÒÃÅÐÅÒÂâºÃÁչ㹷ÕèÁ×´ä´Œ
7.3 ÊÒÃã´ÁÕâÍ¡ÒÊ·Õè¨Ð·íÒ»¯Ô¡ÔÃÔÂҡѺÊÒÃÅÐÅÒÂâ¾á·Êà«ÕÂÁà»ÍÏáÁ§¡Ò๵䴌
8. à¢Õ¹ÊÁ¡ÒÃà¤ÁÕáÊ´§»¯Ô¡ÔÃÔÂÒ·Õèà¡Ô´¢Öé¹ä´Œ ¾ÃŒÍÁ´ØÅÊÁ¡ÒÃ

9. X Y áÅÐ Z ໚¹ÊÒûÃСͺäÎâ´Ã¤ÒϺ͹ «Öè§à¡Ô´»¯Ô¡ÔÃÔÂҴѧÊÁ¡ÒÃà¤ÁÕµ‹Í仹Õé

 72

10. ¹éíÒÁѹª¹Ô´ã´ÁÕÃŒÍÂÅТͧ¡Ã´ä¢ÁѹÍÔèÁµÑÇ໚¹Í§¤»ÃСͺÁÒ¡·ÕèÊØ´

11. àÃÕ§ÅíҴѺ¨Ø´à´×Í´ propanamide pent-2-ene áÅÐ methyl ethanoate

12.à¢Õ¹ÊÁ¡ÒÃà¤Áբͧ»¯Ô¡ÔÃÔÂÒ¡ÒÃàµÃÕÂÁáÍ૵ÒÁÔâ¹à¿¹(¾ÒÃÒ૵ÒÁÍÅ) ¨Ò¡»¯Ô¡ÔÃÔÂÒà¤ÁÕÃÐËÇ‹Ò§
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