CARBOXYLIC ACIDS

Lab exp 3

Mahmoud Mohamed Abdel Moniem

ID: 128697
Abstract

The aim of the experiment is the identification of carboxylic acids, their function group and
to learn the chemistry of carboxylic acid. The experimental procedures are as follows: Testing
the function group by checking their acidity the result is all are soluble in sodium carbonate (all
have acidty), checking its solubility in water, esterification process with alcohol and conc H2SO4
then checking odors and checking if it forms esters, reaction with FeCl3 , oxidation with KMnO4
is to differentiate between ammonium formate (color discharge) and sodium ethanoate (no
change), reaction with CaCl2 is to differentiate between sodium oxalate and sodium tartrate.

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Table of Contents
Abstract ......................................................................................................................................................... 1
Introduction .................................................................................................................................................. 3
Experimental Results .................................................................................................................................... 5
References .................................................................................................................................................. 14

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Introduction

Acidity of carboxylic acids, carboxylic acid are acidic due to the hydrogen in the –COOH group,
Are determined by sodium bicarbonate or sodium carbonate. When adding sodium bicarbonate
To carboxylic acid it forms an effervescence which is a positive result of acidity.

Compassion of acidity for carboxylic acids and alcohols

Carboxylic pKa Alcohols pKa
acid
Formic acid 3.75 Methanol 15.5
HCOOH CH3
Acetic acid 4.76 Ethanol 15.9
CH3OOH CH3CH2

Propionic 4.87 Phenol 9.95

acid C6H5
C3H6O2
(Clark, 2012)

Difference between carboxylic acid & alcohols

Carboxylic acid are polar molecules. They form strong hydrogen bonds, so they have high
Boiling points. Carboxylic acid are regarded as weak acids but is considered much stronger
Acid than alcohols.
Alcohols have higher boiling point due to the intermolecular interaction between molecules of
Alcohol on hydrogen bonding. Alcohols are polar and also alchols are considered weak acids.
(Dunee, 2012)

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 Carboxylic Boiling Solubilty Alcohols Boiling Solubilty
acid points C֯ g/100g of points C֯ g/100g of
water water
Formic acid 100 Soluble Methanol 65 soluble
HCOOH CH3
Acetic acid 118 Soluble Ethanol 78 soluble
CH3OOH CH3CH2

Propionic 141 Soluble Propanol 97 soluble

acid C3H8O
C3H6O2

(Smitchz, 2012)

In carboxylic acid the more hydrogen bonding between molecules the higher boiling points.
Boiling points increase with molar mass. Carboxylic acids which has one to four carbon atoms
Are soluble in water and solubility decreases when carbon chain length increases, so therefore
Dipole forces have less importance and dispersion forces becomes stronger.

In alcohols, alcohols are soluble in water due to the hydroxyl group, which is able to form
Hydrogen bond together with water molecules. The smaller hydrocarbon chain the more soluble
And vice versa. The factor in which the solubility decreases is due to the requirement of more
Energy to overcome hydrogen bonds between alcohol molecules.

(Soderberg, 2012)

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Experimental Results

Carboxylic acids
Unknown 1
Physical Characteristics:

Color: white

Appearance: White monoclinic crystals

Solubility in water: soluble

Chemical reactions:

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 Red color Indicates it could

either Ammonium
formate or sodium
ethanoate

Oxidation using KMnO4 Colorless Color discharge

Gives us CO2 + H2O

Mn+2 MnO2
Ammonium formate

CaCl2 Not applicable Not applicable

Unknown is Ammonium formate write the structure

Comment using Chemical equations

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a

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positive result for acidity. Esterification acids forms esters when reacting it with alcohol and
conc H2SO4. and Reacting it with FeCl3 gives a red color which indicates that the
sample could be either Ammonium formate or sodium ethanoate then reacting it with KMnO4
“Oxidation” gives a color discharge Mn+2 “MnO2” which indicates that the sample is
ammonium formate.
Reaction with FeCl3
HCOONH4 + FeCl3  (HCOO)3 Fe+3 + 3NH4 Cl
Red color
Reaction with KMnO4
HCOONH4 [O]  CO2 + H2O + MnO2

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 Carboxylic acids
Unknown 2
Physical Characteristics:

Color: White

Appearance: Powder

Solubility in water: Soluble

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 Red color Indicates it could

either Ammonium
formate or sodium
ethanoate

Oxidation using KMnO4 No change in color CO2+H2O + heat

Indicates the sample is

Sodium Ethanoate

CaCl2 Not applicable Not applicable

Unknown is Sodium ethanoate write the structure

Comment using Chemical equations.

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a
positive result for acidity and Effervescence is observed Reacting it with FeCl3 gives a red color
which indicates that the sample could be either Ammonium formate or sodium ethanoate then
reacting it with KMnO4“Oxidation” no change in color is observed which indicates that

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the sample is ammonium formate.
Reaction with FeCl3
3CH3COONa + FeCl3  3NaCl + (CH3COO)3Fe Red color
Reaction with KMnO4
CH3COONH4 [O] ∆ CO2 + H2O + Heat

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 Carboxylic acids
Unknown 3
Physical Characteristics:

Color:

Appearance

Solubility in water:

Chemical reactions:

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 No change in color Indicates that sample

Could be sodium

Oxalate or sodium
tartrate.

Oxidation using KMnO4 Not applicable Not applicable

CaCl2 White ppt Ca C2O4+Nacl

Calcium oxalate

Indicates sample is
sodium oxalate

Unknown is Sodium oxalate write the structure

Comment using chemical equations

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a
positive result for acidity and Effervescence is observed Reacting it with FeCl3 gives no change in

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color which indicates that the sample could be either sodium oxalate or sodium tartrate
then reacting it with CaCl2 white ppt is observed which indicates that the sample is sodium
oxalate.
Reaction with CaCl2
C2O4Na2 + CaCl2  Ca C2O4 + NaCl
White ppt. calcium oxalate

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 Carboxylic acids
Unknown 4
Physical Characteristics:

Color: white

Appearance: Crystals

Solubility in water: soluble

Chemical reactions

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 No change in color Indicates that sample

Could be sodium

Oxalate or sodium
tartrate.

Oxidation using KMnO4 Not applicable Not applicable

CaCl2 White ppt sample is sodium

tartrate

Unknown is sodium tartrate write the structure

Comment using chemical equations

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a
positive result for acidity and Effervescence is observed Reacting it with FeCl3 gives no change in
color which indicates that the sample could be either sodium oxalate or sodium tartrate

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then reacting it with CaCl2 white ppt after scratching is observed which indicates that the sample
is sodium tartrate.

Carboxylic acids
Unknown 5
Physical Characteristics:

Color: white

Appearance: crystalline powder

Solubility in water: soluble

Chemical reactions

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 Buff ppt C7O2NaH5 +FeCl3

C2O2H5Fe + NaCl

Indicates it is sodium
benzoate

Oxidation using KMnO4 Not applicable Not applicable

CaCl2 Not applicable Not applicable

Unknown is sodium benzoate write the structure

Comment using chemical equations

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a
positive result for acidity and Effervescence is observed Reacting it with FeCl3 a buff ppt which

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indicates that the sample is sodium benzoate.
Reaction with FeCl3
C7O2NaH5 +FeCl3  C2O2H5Fe + NaCl buff ppt.

Carboxylic acids
Unknown 6
Physical Characteristics:

Color: White

Appearance: Crystals

Solubility in water: soluble

Chemical reactions

Test Observation Result

Reaction with Sod.Carbonate Effervescence occurs Positive result for

acidity

FeCl3 Violet color Indicates it is sodium

salicylate

Oxidation using KMnO4 Not applicable Not applicable

CaCl2 Not applicable Not applicable

Unknown is sodium salicylate write the structure

Comment using chemical equations

The first test is detecting the acidity by reaction with sodium carbonate of the sample, it shows a
positive result for acidity and Effervescence is observed Reacting it with FeCl3 a violet color
appears which indicates that the sample is sodium salicylate.

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References
Clark, J. (2012). chemwiki. Retrieved from chemwiki:
http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Alcohols/Properties_of_Alcohols/Backgr
ound

Dunee. (2012, 3 4). differencebetween. Retrieved from differencebetween:

http://www.differencebetween.com/difference-between-carboxylic-acid-and-vs-alcohol/

Smitchz, A. (2012). 2012books.lardbucket. Retrieved from http://2012books.lardbucket.org/

Soderberg, t. (2012). Chemwiki. Retrieved from

http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Organic_Chemistry_With_a_Biological_E
mphasis/Chapter_12%3A_Acyl_substitution_reactions/Section_12.1%3A_Introduction_to_carb
oxylic_acid_derivatives_and_the_nucleophilic_acyl_substitution_reaction

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