GV: Nguyn Th Nguyt

B mn Ha hc - HYHN
1

1. Acid carboxylic
1.1. nh ngha Phn loi
nh ngha: R(COOH)n
Theo gc R

acid bo
acid thm

Phn loi:
Theo n

acid monocarboxylic
acid polycarboxylic
2

H-COOH

CH3-COOH

acid methanoic

acid ethanoic

acid formic

acid acetic

CH2=CH-COOH

HOOC-COOH

acid propenoic

acid ethandioic

acid acrylic
CH3
CH3-CH-CH2-COOH

acid oxalic
acid 3-methyl butanoic
3

CH3
CH2=C-CH2-COOH acid 3-methyl but-3-en-1-oic
HOOC-CH=CH-COOH
COOH

COOH

acid butendioic

acid cyclohexancarboxylic

acid benzencarboxylic
acid benzoic
4

Cng thc

Tn IUPAC

H-COOH a.methanoic

Tn th
ng

Ngun gc

a.formic

Formica: con kin

a.acetic

Acetum: dm

a.propyonic

Protospion: sa

CH3-(CH2)2- COOH a.butanoic

a.butyric

Butyrum: b

CH3-(CH2)3- COOH a.pentanoic

a.valeric

Valer: cy n lang

CH3-(CH2)4- COOH a.hexanoic

a.caproic

Caper: con d

CH3-(CH2)5- COOH a.heptanoic

a.enantic

Oenanthe: hoa nho

a.oxalic

H cy oxalic

CH3-COOH a.ethanoic
CH3-CH2-COOH a.propanoic

HOOC-COOH a.ethandioic

HOOC-CH2-COOH a.propandioic a.malonic

Malon: to

HOOC-(CH2)2-COOH a.butandioic

a.sucinic

Sucinium: h phch

HOOC-(CH2)3-COOH a.pentandioic

a.glutaric

Gluten:protein bt

HOOC-(CH2)4-COOH a.hexandioic

a.adipic

Adeps: cht bo

1.2. Danh php

Danh php IUPAC:
Acid bo
Acid + tn hydrocarbon + oic
Acid vng
Acid + tn hydrocarbon + carboxylic
Danh php thng thng: theo ngun
gc
6

1.3. Tnh cht ho hc

1.3.1. Tnh acid
RCOOH + H2O

RCOO + H3O+

Cl3C-COOH, CH3-COOH, (CH3)3C-COOH, H2CO3

pKa:
0,7
4,76
5,06
6,5

2R- COOH + Mg
2CH3COOH+Na2CO3
H2C2O4 + CaCl2

(R- COO)2Mg + H2
2CH3COONa + CO2+ H2O
CaC2O4 + 2HCl
7

1.3.2. Phn ng este ho

RCOOH + ROH

RCOOR + HOH

C th to ra este vng niCH

phn
t +
3
H
CH3-COOH + HO-CH2-CH2-CH-CH3
CH2 O
CH2 OH
CH3-COOCH2-CH2-CH-CH3 + H2O
C O
COOH
isoamyl acetat CH3
CH2 CH2
CH2 CH2
lacton
8

1.3.3. Phn ng to halogenid acid

RCOOH + SOCl2
RCOOH + PCl5

RCOCl + SO2 + HCl

RCOCl + POCl3 + HCl

Ch :
RCOCl + H2O

RCOOH + HCl

RCOCl + NH3

RCONH2 + HCl

RCOCl + ROH

RCOOR + HCl

RCOCl + C6H6

RCOC6H5 + HCl
9

1.3.4. Phn ng to anhydrid acid

R
C

O
2RCOOH

(RCO)2O + NH3

(RCO)2O + H2O

RCOCl + NaOOCR
(RCO)2 + H2O

R
C

ROCOCOR+ NaCl
2RCOOH
RCONH2 + RCOOH

(RCO)2O + ROH

RCOOR+ RCOOH

(RCO)2O + C6H6

RCOC6H5 + RCOOH
10

1.3.5. Acid dicarboxylic

HOOC-(CH2)n-COOH
0
1
t
,
C
n
0C
0
=2
0
=
8
n 0 -1
(CH
)
,
2
n
3
C
0
6
1

RCOOH + CO2
H

COOH
C
C

COOH
H
acid maleic

C
O

+ H 2O
O

COOH
O

OH

OH

COOH
acid meso tartric

11

HOOC

H
C

acid fumaric

COOH
O
COOH

COOH
H
HO

OH
H
COOH

acid L tartric

HO
H

H
OH
COOH

acid D tartric
12

COOH

O
C

t0

O + H 2O

COOH
acid phtalic
H

C
O anhydrid phtalic
H

COOH
C

C
H

COOH

acid maleic

C
O + H2O
C

O
anhydrid maleic

13

1.4. ng dng ca mt s acid

HCOOH dng trong cng nghip dt, thuc da.
CH3COOH (E260) lm dm n. Dng trong
cng nghip lm dung mi, tng hp cht thm,
phm nhum...
C6H5COOH (E210) dng chng khun trong
kem nh rng, nc sc ming, m phm, trong
cng nghip hp. C6H5COONa lm thuc ho.
14

 acid butyric c tc dng n nh glucose mu,

c ch tng hp cholesterol gan, gim pH i
trng, bo v v lm tng hp th cht khong
trong thc n, kch thch sinh sn t bo T h tr,
khng th, bch cu tng cng min dch,
tng vi khun c ch i trng,
acid oxalic, acid sucinic sinh ra trong qu trnh
chuyn ha cht trong c th.
15

 acid stearic (E570) dng trong dc phm.

acid trans butendioic (acid fumaric, E297)
l tc nhn acid ha, cht chng oxy ha, cht
to hng, lm thuc...
acid oleic l tc nhn nh ha trong thuc
dng ti ch v trong thc phm, cht dn
qua da. Acid oleic iod ha c dng trong
chn on hnh nh.
16

2. Este
2.1. nh ngha Phn loi
nh ngha: RCOOR
Phn loi:
Este
Acid
Alcol
Este
bo thp,
bo thp,
hoa qu
trung bnh
trung bnh
Glycerid bo cao, s C
glycerol
(lipid)
chn, thng
Serid (sp) bo cao, thng
bo cao
Sterid
bo cao
vng (cholesterol)
17

2.2.
phpho hc
2.3. Danh
Tnh cht

2.3.1. Phn ng x phng ho

R

HO

O
OR

OR C OR
OH

2.3.2. Phn ng to amid

R

NH3

O
OR

OR C OR
+
NH3

R C

+ ROOH

RCOO- + ROH
O
R C + + RONH3
RCONH2 + ROH
18

CH3COOCH3 + NH3

CH3CONH2 + CH3OH

2.3.3. Phn ng vi thuc th Grignard

R

O
OR

CH3 C

1.+ 2RMgX(ether)
2.+ H-OH

O 1.+ 2CH MgX(ether)

3
OCH3

2.+ H-OH

R
R C R
OH
CH3
CH3 C CH3
OH
19

2.3.4. Phn ng kh este

RCOOR

1.+ LiAlH4(ether)
2.+ H-OH

CH3COOCH3

RCH2OH + ROH

1.+LiAlH4(ether)
2.+ H-OH

CH3CH2OH + CH3OH

20

2.3.4. Phn ng ngng t Claisen

O

R
1.+ RO2.+ H-OH

2 CH2 C
R
OR

CH2 C
CH
R

O
C
OR

+ ROH
2CH3COOCH3

1.+CH3ONa
2.+ H-OH

CH3COCH2COOCH3+CH3OH

methyl acetoacetat
21

2.4.
Esteng
hoa dng
qu dng
trongsch
bin thc phm, gii
ca mt
este
kht,hng liu trong dc phm v m phm.
Cht bo cung cp nng lng chnh cho c th.
Dietylphtalat (DEP) cha bnh ngoi da, lm
dung mi, cht ha do,...
C6H5COOCH2C6H5 lm cht ha do, dung
mi, cht nh hng, lm thuc
Sp ong lm cng thm cc thuc kem thuc
m, nh bng vin bao ng, iu chnh
im chy ca vin t, n nh nh dch, t
dc ch phm gii phng c kim sot
22

3. Hydroxy acid
3.1. Alcol acid

HOOC-CH-CH
CH
3-CH-COOH
3.1.1.
nh ngha Phn
loi Danh2-COOH
php
OH

OH

acid lactic

acid malic

HOOC-CH-CHCOOH
OH OH

CH2COOH
HO-C-COOH
CH2-COOH

acid tartric

acid citric
23

3.1.2. Tnh cht ho hc

Tnh acid:
Acid

Ka

CH3-COOH 1,76.10-5

Alcol acid

Ka

HO-CH2-COOH 152.10-4

CH3-CH2-COOH 1,35.10-5 CH3-CHOH-COOH 1,4.10-4

Tnh cht ring:

- alcol acid
- Gy mch khi un nng vi H2SO4 long
R-CHOH-COOH

RCHO + HCOOH
24

0
t
CH3- CH - COOH
CH3- CHO + HCOOH
OH
aldehyd acetic acid formic
acid lactic

- Tch nc to este vng (lactid)

R
2 R-CH-COOH
OH

t
p

O
CH

C
O + 2H2O

O
C
O

HC

lactid

R
25

- To phc mu vng vi FeCl3

- alcol acid to acid cha no khi un nng
0
t
R-CH=CH-COOH + H2O
R-CH-CH2-COOH
OH
- alcol acid to lacton
R-CH-CH2-CH2-COOH
OH

R CH CH2
CH2 O + H2O
C
O
-

26

3.2. Phenol acid

COOH

Acid 2-hydroxy benzoic

OH

Acid salicylic

Tnh cht ho hc
Phn ng vi dung dch kim
COOH
+ 2NaOH
OH

COONa
+2 H2O
ONa
H
27

 Phn ng vi dung dch mui carbonat

COOH
+ Na2CO3
OH
COONa
+ Na2CO3
OH

COONa
+ CO2 + H2O
OH
COONa
+ NaHCO3
ONa

Phn ng este ha
COOH
H2SO4
+ CH3OH
OH

COOCH
3 O
+ H
2
OH
methyl salicylat

28

COOH
+ (CH3CO)2O
OH

COOH
+ CH3COOH
O-C-CH3
O

acid acetylsalicylic (aspirin)

Phn ng to phc
COOH
pH 4
+ FeCl3
OH

COO +
Fe + 2H+ + 3ClOH
29

2.4. ng dng ca mt s hp cht

Acid citric c trong chanh, cam, qut, bi, du,
mn...Cha ng c kim, sn xut nc gii kht.
Acid malic c trong to, nho, thanh tr cha
chn. Dng to v chua, che mi kh chu ca
thuc, dng trong bt si bt, nc sc ming,
vin lm sch rng. Lm cht chng oxy ha cho
du thc vt. Dng thay th acid citric, acid tartric
trong cng nghip nc gii kht, nc hoa qu...
HO-CH2-COOH (acid glycolic) c trong c ci
ng...Dng trong cng nghip nc gii kht.

30

Acid L (+) lactic c trong c, mu, nc tiu.

Acid lactic dng trong thc phm, ung, dc
phm v m phm, lm tc nhn acid ha v to v
chua. Bo qun thuc tim v thc phm. iu tr
chuyn ha acidtng cng kh nng tiu ho
ca protein sa, kch thch s tit dch d dy.
Hai ng phn c hp th qua ng rut,
L- hp th hon ton v nhanh chng chuyn ho
trong tng hp glycogen, D- chuyn ho tc
thp hn v sn phm c bi tit qua nc tiu.
31

 Acid salicylic st khun dng cha bnh ngoi da

Methyl salicylat dng trong thuc xoa bp, cha
thp khp.
Acid acetyl salicylic (aspirin) lm thuc h nhit,
gim au, c tc dng gim dnh ca cc tiu
cu gim nguy c hnh thnh cc cc mu ng.
Dn xut ca acid
p-amino salicylic (P.A.S)
l thuc khng lao.

COONa
OH
NH2

P.A.S sodic
32