6 heterofunctional comp укороченный

2. HYDROXY (OXY) ACIDS
ISOMERISM, NOMENCLATURA
1. Chain СН3
СН3 СН2 СН СООН СН3 С СООН
ОН ОН
2-hydroxybutanoic acid 2-hydroxy- 2-methylpropanoic
acid
ОН-group position
СН3 СН СН2 СООН СН2 СН2 СН2 СООН
ОН ОН
3-hydroxybutanoic acid 4-hydroxybutanoic acid

3. Hydroxy acids.
СOOH СOOH СOOH
CHOH CH2 CHOH CH2
CH3 CHOH CHOH C OH
Lactic acid COOH COOH COOH
Malic acid Tartaric acid CH2
COOH
Citric acid
Salicylic acid
CОOH
COOH
OH

4. [α]D =
L*100
c*l

5. Optical Isomerism
1.Enantiomerism (Mirror Isomerism)
2.Diastereomerism
R
R''' C* R' Assymetrical Carbon (C* -SP
3
- hybrid)
R''
Lactic acid:
Enantiomers
COOH HOOC Glyceric aldehyde
H C* OH HO C* H C O C O
CH3 CH3 H H
D(-) – Lactic acid (+)L – Lactic acid H C* OH НО C* H
CH2OH CH2OH

6. Chiral objects

7. Chiral moleculars

8. X=2
n
, n-number of assymetrical carbons (chiral)
X- number of stereoisomers
COOH COOH COOH COOH
H C* OH НО C* H H C* OH HO C H
HO C* H H C* OH H C* OH HO C H
COOH COOH COOH COOH
Clockwise Counter clockwise
D(+) – Tartaric L(-) –Tartaric Mesotartaric
acid acid acid
Enantiomers Diastereomers
(Grape acid - Racemic mixer)
Tartaric Acid

9. 1. R CH COOH H+
+ R CH COO-
OH OH
2. R CH COOH + NaOH R CH COONa
OH OH
3. R CH COOH + R'OH R CH COOR' + H2O
OH OH Ether
4. Haloanhydrates, amides.
R CH C R CH C
OH OH
-Н2О
O
Cl
O
NH2
Chemical Properties

10. 5. R СН С
ОН
6. R CH C
OH
О
ОН
+ 2Na R CH C
ONa
O
ONa
+ H2
O
OH
+ [O] R C C
O
O
OH
Oxoacid

11. t
0
, Н
+
-H2O
1. Decomposition of α-hydroxy acids
R' O
R CH COOH R C + H COOH
OH H Formic acid
(R')
2.
R CH OH HO C O
+ CH R R HC C O
C HO O C CH R
α-hydroxy acid ОН O Lactid
t
0
α
О
Speсial Properties.
О

12. b)
R CH CH2 COOH R CH CH COOH
ОН unsaturated acid
β-hydroxy acid
c) CH2 CH2 H2C CH2
R CH C O R CH C O
OH HO O
γ-lactone
Oxidation O
HO - CH2 - (CH2)n - COOH → C - (CH2)n COOH
H ↓ [O]
HOOC - (CH2)n - COOH
[O]
CH3 -CH- COOH → CH3 – C- COOH → CH3 - C O
OH O -CO2 H
t
0
-H2O
β
γ
-H2O

13. COOH
COOH
CH-O
CH-OH
COOH
COOH
HO-CH
O-CH
Cu
HO
OH
H
H
COOH
COOH
CH-O
CH-O
H
COOH
COOH
O-CH
O-CH
H
Cu
:
:
+
+
Test on Tartaric Acid
-2Н2О

14. Phenoloacids.
COOH COOH COOH
OH
OH
OH
+ FeCl3
Violet colour
о-Oxybensoic acid м- Oxybensoic acid p-Oxybensoic acid
(Salicilic)
O Na
+ CO2
125
0
, 5 атм.
OH
C
O Na
+HCl
-NaCl
OH
COOH
pKa=2,98O
H
O
C
OH
О

15. O C
O
CH3
C
O
OH
CH3C
O
OH
OH
COOH
Acetylsalicilic acid
(aspirin)
+Na2CO3
-CO2, -H2O
OH
OH
OH
C
C
C
O
O
O
O Na
O CH3
O C6H5
Methylsalicilate
Phenylsalicilate
(salol)
+СH3OH (H
+
)
-H2O
-H2O
C6H5OH

16. СООН
ОН
ОН
НО
tº
ОН
ОННО
Gallic acid Pyrogallol

17. COOH COOH
OH
OH
HO
OHNH2
P-Aminosalicilic acid
Gallic acid
С6H5 CH COOH
OH
Mindalic acid

18. Oxoacids (Ketoacids).
Trivial name IUPAC name Structure
Glioxalic Oxoethanoic
Н С СOOH
O
Pruvic 2-Oxopropanoic
H3C C COOH
O
Acetoacetic 3-Oxobutanoic
H3C C CH2 COOH
O
Oxaloacetic 2-Oxobutanedioic HOOC C CH2 COOH
O
α-Ketoglutaric 2-Oxopentanedioic HOOC- C CH2 - CH2
COOH
o

19. Oxoacids (Ketoacids) Kеtо-Enol
Tautomerism
СH3
C O
H C H
C O
O C2H5
δ+
δ+
δ-
δ-
CH3
C OH
CH
C O
O C2H5
Acetoacetic ether
Кеtо-form
93%
Еnol-form
7%