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Carboxylic Acid Reactions Formic Acid, Acetic Acid, Oxalic Acid, Citric Acid, Tartaric Acid.

Carboxylic acids can be prepared through various reactions. Formic acid can be prepared by distilling oxalic acid or from carbon monoxide and a base. Acetic acid can be prepared from acetylene, ethylene, methanol, or through fermentation of molasses. Unsaturated fatty acids like oleic acid contain double bonds in their carbon chains. Dicarboxylic acids include oxalic acid, malonic acid, and succinic acid. Tartaric acid is found in grapes and used in baking powder production. Citric acid is found in fruits and is an intermediate in metabolism.

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158 views4 pages

Carboxylic Acid Reactions Formic Acid, Acetic Acid, Oxalic Acid, Citric Acid, Tartaric Acid.

Carboxylic acids can be prepared through various reactions. Formic acid can be prepared by distilling oxalic acid or from carbon monoxide and a base. Acetic acid can be prepared from acetylene, ethylene, methanol, or through fermentation of molasses. Unsaturated fatty acids like oleic acid contain double bonds in their carbon chains. Dicarboxylic acids include oxalic acid, malonic acid, and succinic acid. Tartaric acid is found in grapes and used in baking powder production. Citric acid is found in fruits and is an intermediate in metabolism.

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CARBOXYLIC ACID

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Formic Acid or download this file free, to view the file
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- HCOOH

PREPARATION

1. Distillation of oxalic acid

°C(COOH)2 120°C HCOOH + CO2

2. From CO and a base


150-200 °C
CO + NaOH HCOONa
100-150 psi

2HCOONa + H2SO4 2HCOOH + Na2SO4

REACTION

1. Oxidation – formic acid and its salts are reducing agents

(HCOO)2Hg 2Hg + CO2


AgNO3
HCOOH + TOLLENS Ag° (Silver Mirror) + CO2
NH4OH
2. Decomposition

HCOOH + H2SO4 CO + H2O

HCOOH CO2 + H2O


165°C
3. Esterification
HCOOH + CH3OH ⇌ HCOOCH3 + H2O

Acetic Acid

- CH3COOH

PREPARATION

1. From Acetylene
HgSO4 K2Cr2O7
H-C ≡ C-H + HOH CH3CHO CH3COOH
H2SO4, 70-100°C H2SO4
2. From Ethylene

H2-C=C-H2 + H2SO4 C2H5HSO4

2H2-C=C-H2 + H2SO4 (C2H5)2SO4

C2H5SO4 + (C2H5)2SO4 3 C2H5OH + H2SO4

C2H5OH CH3COOH

3. Synthesis from methanol


350°C
CH3OH + CO + H2 CH3COOH + CH3COOCH3 + H20 + CH3OH *** excess CH3OHis recycled in the process
700atm, Activated
Charcoal

4. From Pyroligneous acid

- Derived from destructive distillation of wood. Wood is heated in the absence of air, gives off gaseous mixture which contains H 2, CO, CO2, CH4 and N2 gases. The

vapor that condenses forms and acidic liquor called pyroligneous acid which contains 80% H2O 2% CH3COOH acetic acid, and 4% crude CH3OH and 9% coal tar

and oils. The mixture is purified by fractional distillation.


5. Fermentation
fermented Bacterium
a. Molasses C2H5OH CH3COOH
Acetobacter

ACETIC ANHYDRIDE
CH3 - C = O

CH3COOH + HOOC-CH3 O
CH3 - C = O

UNSATURATED FATTY ACIDS

a. Oleic Acid C17H33COOH (double bond at C9)

b. Linoleic Acid C17H31COOH (2 double bonds at C9 and C12)

c. Linolenic Acid C17H29COOH (3 double bonds at C9, C12, C15)

d. Arachidonic Acid C19H31COOH (4 double bonds at C5, C8, C11, C14)

*LINOLEIC, LINOLENIC, ARACHIDONIC acid are essential fatty acids

DICARBOXYLIC ACID

COMMON NAME IUPAC NAME FORMULA


Oxalic Acid Ethanedioic acid (COOH)2
Malonic Acid Propanedioic acid CH2-(COOH)2
Succinic Acid butanedioic acid (CH2)2-(COOH)2
Glutaric Acid pentanedioic acid (CH2)3-(COOH)2
Adipic Acid hexanedioic acid (CH2)4-(COOH)2
Tartaric Acid 2,3 dihydroxybutanedioic acid C4H6O6
Oxalic Acid
- Acid found in rhubbards, spinach and alugbati
PREPARATION
V2O5
a. Corn cobs, sawdust oxalic acid
HNO3
375°C
b. v2HCOONa (COONa)2 + H2
(COONa)2 + H2SO4 (COOH)2 + Na2SO4
Tartaric Acid
- Acid found in grapes, used in the production of yeast.
REACTIONS
1. Formation of salt
CHOHCOOH CHOHCOOK
+ limited KOH
CHOHCOOH CHOHCOOH
*K acid tartrate or cream of tartar, an acid used as laxative and in the preparation of baking powder.
CH CH
2. Tartar emetic formation
CHOHCOOK CHOHCOOK
+ Sb2O3
CHOHCOOH CHOH(COOSbO)2⋅H2O
*K-antimonyl tartrate used as emetic and mordant in dyeing
CH CH
Citric Acid
- Acid found in sugar beets, calamansi, oranges’ an intermediate product in metabolism
2hydroxy-1,2,3-propanetricarboxylic acid
CH2 - COOH
HO-C-COOH
CH2 - COOH
PREPARATION
- Calamansi juice + CaCO3 Ca Citrate Citric acid + CaSO4
Conc. H2SO4

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