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Carboxylic Acids and Their
Derivatives
Lab Performed by 1Nur9-Grp 5
Elias, Jose Emmanuel D.
Esperanza, John Ruben A.
Flores, Norman Karl
Genilla, Jonathan L.
Manalo, Michelle C.
Carboxylic Acids
• INTRODUCTION
• Carboxylic acids are weak acids. They have sour or tart taste,
produce hydronium ions in water, and neutralizes base. Carboxylic
acid reacts with an alcohol to form an ester. In an ester, the –H of
the carboxylic acid is replaced by an alkyl group. Aspirin is an ester
as well as carboxylic acid. Amines and amides are organic
compounds that contain nitrogen. Many nitrogen containing
compounds are important to life as components of amino acids,
proteins and nucleic acid: DNA and RNA. Many amines that exhibit
strong physiological activity are used in medicine as decongestants,
anesthetics, and sedatives. Amides are derived from carboxylic
acids and amines. In biochemistry, the amide bond is called the
peptide bond, which links amino acids in proteins.
CARBOXYLIC ACIDS
• CARBOXYLIC ACID
• In carboxylic acids, the functional group is the carboxyl group,
which is combination of the carbonyl group and hydroxyl group.
• The carboxyl functional group maybe attached to an alkyl group or
an aromatic group.
•
O
•
‖
•  —OH –COOH CO2H
C
•
• You encounter carboxylic acids when you use a vinegar salad
dressing, which is a solution of acetic acid and water, or experience
the sour taste of citric acid in grapefruit or lemon.
Solubility, Effervescence, and
Precipitate Formation of Carboxylic
Acids and Amines
Contents
• Results
• Explanations
– Intermolecular bonding
– Chemical equations
Results
Sample

Solubility in H2O

+ Na2CO3 →
Effervescence

+ HCl →
Formation of
precipitate

Acetic acid

Soluble

2 – 3 drops

No precipitate in
yellow solution

Triethylamine

Soluble

5 drops

Bubbly brown top
layer (precipitate)
with liquid bottom
layer

Benzoic acid

Insoluble

5 drops, still no
effervescence

White precipitate
on top of colorless
liquid
Explanations
Intermolecular bonding
Acetic acid

..
O
II . .
CH3 – C – . . +
OH

.. ..
O
H

H

Acetic acid is soluble in water due to its one – carbon
length and three hydrogen bonding possibilities.
•Carbonyl oxygen with hydrogen of water
•Hydroxyl oxygen with hydrogen of water
•Hydroxyl hydrogen with oxygen of water
Triethylamine

..
CH3 – N – CH3
I
CH3

.. ..
O
H

H

Triethylamine is slightly soluble in water due to the nitrogen
in the amine forming an H – bond with a hydrogen of water.
Primary and secondary amines have nitrogen (amine) to
hydrogen (water) bonding and hydrogen (amine) to oxygen
(water) bonding. But in triethylamine, a tertiary amine, only
the nitrogen (amine) to hydrogen (water) bonding is possible.
Benzoic acid
..
O
II ..
C – OH +
..

.. ..
O
H

H

Benzoic acid is insoluble in water for two reasons.
•The carboxyl group is bonded to the benzene
ring. Benzene is insoluble in water.
•There are seven carbons in the benzoic acid
molecule. Carboxylic acids with five or more
carbons are insoluble in water.
Chemical equations
Acetic acid
CH3COOH + H2O + Na2CO3 → CH3COONa + H2O + CO2↑

Bubbles of carbon dioxide were formed when sodium
bicarbonate was added to the acetic acid solution. And, a
carboxylic acid salt (sodium acetate) was formed (and
dissolved in water).
CH3COONa + H2O + HCl → CH3COOH + NaCl + H2O
No precipitate was formed after the addition of
hydrochloric acid to the sodium acetate solution. Since
the products (acetic acid and sodium chloride) were both
dissolved in water, no precipitate was formed.
Triethylamine
1. (CH3CH2)3N + H2O + Na2CO3 →
(CH3CH2)3N + Na2CO3 + H2O + CO2↑

2. (CH3CH2)3N + Na2CO3 + H2O + HCl →
(CH3CH2)3N + H2O + NaCl + CO2↑
The triethylamine remained untouched after the addition of sodium
bicarbonate. Instead, the sodium bicarbonate decomposed into
sodium carbonate, water, and carbon dioxide (effervescence) (eq. 1).
Then, the hydrochloric acid was added, yielding sodium chloride and
carbonic acid. Carbonic acid eventually broke down into water and
carbon dioxide, thus producing a second batch of effervescence.
Once again, the triethylamine was untouched after the addition of
hydrochloric acid (eq. 2).
1. C6H5COOH + H20 + NaHCO3 → no reaction
2. C6H5COOH + H20 + NaHCO3 + HCL →
C6H5COOH + NaCl + H2O

• No bubbles were formed in the benzoic acid
solution after the addition of sodium
bicarbonate. In fact, benzoic acid is insoluble in
water at room temperature, but soluble in water
at boiling point (eq. 1). The benzoic acid crystals
were seen floating on water surface, even after
the addition of hydrochloric acid. Instead, the
sodium bicarbonate reacted with hydrochloric
acid, producing sodium chloride and carbonic
acid, which later broke down into carbon dioxide
and more water (eq. 2).
Benzoic acid
C6H5COOH + H2O + Na2CO3 → no reaction
There was no bubble formation after adding sodium
bicarbonate since benzoic acid is insoluble in water at
room temperature (but soluble at water’s boiling point).
C6H5COOH + H2O + Na2CO3 + HCl → C6H5COOH + H2O + NaCl +
CO2↑
The white “precipitate” in this chemical reaction (after the
addition of sodium bicarbonate and hydrochloric acid)
was the insoluble benzoic acid. The only reaction that
occurred here was between the added compounds
(sodium bicarbonate and hydrochloric acid), which
formed sodium chloride, more water, and carbon dioxide
effervescence.
Study Question 1 for Solubility
• Account for the difference in solubility: the
carboxylic acids and amines in 1) water and 2)
sodium bicarbonate and 3) hydrochloric acid.
• Intermolecular bonding and solubility in
water
• Acetic acid is soluble in water because of the
following reasons, besides from its polarity
(the carboxyl group provides the acid’s
polarity).
Study Question 1 for Solubility
• It has only two carbons. Aldehydes and ketones
with at most four carbons are infinitely soluble in
water.
• There are three hydrogen bonding possibilities in
acetic acid.
– Carbonyl oxygen H – bonds with hydrogen of water.
– Hydroxyl oxygen H – bonds with hydrogen of water.
– Hydroxyl hydrogen H – bonds with oxygen of water.
Study Question 1 for Solubility
• Trimethylamine is partly soluble in water due to
the nitrogen in the amine molecule forms an H –
bond with hydrogen of a water molecule. Primary
and secondary amines have nitrogen (amine) to
hydrogen (water) bonding, as well as hydrogen
directly bonded to nitrogen (amine) to oxygen
(water) bonding. But in triethylamine, a tertiary
amine, only the nitrogen (amine) to hydrogen
(water) bonding is possible, because no hydrogen
is directly bonded to the nitrogen.
Study Question 1 for Solubility
• Benzoic acid is insoluble in water at room
temperature (but soluble in hot water) for two
reasons.
• The carboxyl group is bonded to a benzene
ring. Benzene is nonpolar and insoluble in
water.
• There are seven carbons in the benzoic acid,
six in the benzene ring plus one carboxyl
carbon.
Study Question 1 for Solubility
•
•
•
•

Chemical reactions and equations
CH3COOH + H2O + Na2CO3 → CH3COONa + H2O + CO2↑
CH3COONa + H2O + HCl → CH3COOH + NaCl + H2O
Addition of sodium bicarbonate (Na2CO3) to the acetic
acid solution produced effervescence, carbon dioxide
bubbles. Also, a carboxylic acid salt was produced,
sodium acetate (eq. 1). Later, hydrochloric acid was
added to the sodium acetate solution. This reaction
yielded acetic acid and sodium chloride; both products
are soluble in water. Thus, no precipitate was formed
after adding hydrochloric acid (eq. 2).
Study Question 1 for Solubility
• (CH3CH2)3N + H2O + NaHCO3 → (CH3CH2)3N + Na2CO3 + H2O + CO2↑
• (CH3CH2)3N + Na2CO3 + H2O + HCl → (CH3CH2)3N + H2O + NaCl +
CO2↑
• The triethylamine remained untouched after the addition of sodium
bicarbonate. Instead, the sodium bicarbonate decomposed into
sodium carbonate, water, and carbon dioxide (effervescence) (eq.
1). Then, the hydrochloric acid was added, yielding sodium chloride
and carbonic acid. Carbonic acid eventually broke down into water
and carbon dioxide, thus producing a second batch of
effervescence. Once again, the triethylamine was untouched after
the addition of hydrochloric acid (eq. 2).
Study Question 1 for Solubility
• C6H5COOH + H2O + NaHCO3 → no reaction
• C6H5COOH + H2O + NaHCO3 + HCl → C6H5COOH + NaCl +
H2O
• No bubbles were formed in the benzoic acid solution after
the addition of sodium bicarbonate. In fact, benzoic acid is
insoluble in water at room temperature, but soluble in
water in hot water (eq. 1). The benzoic acid crystals were
seen floating on water surface, even after the addition of
hydrochloric acid. Instead, the sodium bicarbonate reacted
with hydrochloric acid, producing sodium chloride and
carbonic acid, which later broke down into carbon dioxide
and more water (eq. 2).
AMINES, AMIDES AND
SAPONIFICATION
AMINES
• Amines are considered as derivatives of
ammonia (NH3) in which one or more
hydrogen atoms is replaced with alkyl or
aromatic groups. For example, in
methylamine, a methyl group replaces one
hydrogen atoms in ammonia. The bonding of
two methyl groups gives dimethylamine, and
the three methyl groups in trimethylamine
replace all the hydrogen atoms in ammonia.
CLASSIFICATION OF AMINES
• Amines are classified the same way as
alcohols by counting the number of carbon
atoms directly bonded to a nitrogen atom. In a
primary amine, one carbon is bonded to a
nitrogen atom. In a secondary amine, two
carbons are bonded to the nitrogen atom, and
a tertiary amine has three carbon atoms
bonded to the nitrogen.
AMINES
Name
Primary Amine

Ethylamine

Secondary Amine Dietheylamine

Tertiary Amine

Triethylamine

Quaternary

Tetraethylammonium

Ammonium salt

bromide

Structure
PROPERTIES OF AMINES
• Amines have higher boiling points than alkanes of
similar mass, but lower than the alcohols.
• Because amines contain a polar N—H bond, they form
hydrogen bonds. However, nitrogen is not as
electronegative as oxygen, which makes the hydrogen
bonds in amines weaker. The —NH2 in primary amines
can form more hydrogen bonds, which gives them
higher boiling points than the secondary amines of the
same mass. It is not possible for tertiary amines to
hydrogen bond with each other(no N—H bonds), which
makes their boiling points much lower and similar to
those of alkanes.
PROPERTIES OF AMINES
• Amines are stonger proton acceptors than oxygencontaining organic compounds such as alcohols and
ethers; that is, they are stronger bases than these
compounds. A 0.1 M aqueous solution of
methylamine has a pH of 11.8 and a 0.1 M of
aqueous solution of aniline has a pH of 8.6. these
solutions are sufficiently basic to turn red litmus
paper blue. Carboxylic acid salts are the only other
type of organic compound sufficiently basic to turn
red litmus paper red.
AMIDES
• Amides are derivatives of carboxylic acid in
which an amino group replaces the hydroxyl
group
AMIDATION
• An amide is produced in a reaction called
amidation, in which a carboxylic acid reacts
with ammonia or a primary or secondary
amine. A molecule of water is eliminated, and
the fragments of the carboxylic acid and
amine molecules join to form the amide,
much like the formation of ester. Because a
hydrogen atom must be lost from the amines,
only primary and secondary amines undergo
amidation.
ACETAMIDE

• -unlike other water-insoluble organic substances, saponification of
an amide releases ammonia which is very distinct for its pungent
and urine like smell.
• *red litmus paper turned blue on ACETAMIDE due to the presence
of ammonia(weak base)
• -nitrogen atom in the molecule has a lone pair making it a proton
acceptor
BASICITY OF AMINES
• Because amines acts as weak bases by
accepting protons from water and producing
hydroxide ions, their aqueous solutions are
basic.
PROPERTIES OF AMINES
• Most of the K value for amines are less than
10^-3, which means that the equilibrium
favored the undissociated amine molecules.
Aqueous solutions of amines have basic pH
values and turn litmus paper blue.
HYDROLYSIS OF AMIDES
• The most important reaction of amides is
hydrolysis. In amide hydrolysis, the bond
between the carbonyl carbon atom and the
nitrogen is broken, and free acid and free
amine are produced. Amide hydrolysis is
catalyzed by acids, bases, or certain enzymes;
sustained heating is also often required.
HYDROLYSIS OF AMIDES
• Acidic or basic hydrolysis conditions have an
effect on the products. Acidic conditions
convert the product amine to amine salt. Basic
conditions convert the product carboxylic acid
to a carbxylic acid salt.
• (PICTURE COURTESY OF BOOK page 715)
HYDROLYSIS OF AMIDES
• Amide hydrolisis under basic conditions is also
called amide saponification, just as ester
hydrolysis under basic conditions is called
ester saponification.
• (PICTURE COURTESY OF BOOK PAGGE 715)
HYDROLYSIS OF AMIDES
• Amide bonds are formed by the elimination of
water. The reverse reaction called hydrolysis
occurs when water is added back to the amide
bond to split the molecule. When an acid is
used, the hydrolysis products of an amide are
the carboxylic acid and the ammonium salt. In
base hydrolysis, the amide produces the salt
of carboxylic acid and ammonia or amine.
HYDROLYSIS OF AMIDES
• Of the various acid derivatives, amides are the least
reactive toward nucleophilic attack, because the unshared
electron pair on the nitrogen is delocalized to the carbonyl
carbon through resonance.
• Thus, unlike most acyl halides or anhydrides, amides must
be heated to boiling with aqueous acid or base in order to
hydrolyze them. For a primary amide, the product will be
ammonium ion and the acid (for acidic hydrolysis) or
ammonia and carboxylate ion (for alkaline hydrolysis). The
reaction mechanisms are similar to those for the hydrolysis
of other acid derivatives.
SAPONIFICATION
• Procedure:
• 1. Prepare 2 clean and dry text tubes. Place
1.0 triethylamine in tube 1, and pinch-amount
of acetamide in tube 2. add 1.0 of dilute 6N
NaOH solution to each tube and mix
thoroughly.
• 2. Heat all 2 tubes in a boiling water bath for
two minutes.
LAB EXPERIMENT: RESULTS
SAMPLE

REACTION WITH
LITMUS PAPER

TRIETHYLAMINE

THE RED LITMUS PAPER
TURNED BLUE

ACETAMIDE

THE RED LITMUS PAPER
TURNED BLUE
ESTERS
ESTERS
• An ester is similar to a carboxylic acid, except
that the oxygen of the carboxyl group is
attached to a carbon and not to hydrogen. In
ester, the –H of the carboxylic acid is replaced
by an O-akyl (alkoxy) group. Fats known as
Triglycerides are esters of glycerol and fatty
acids, which are long-chain carboxylic acids.
Esters produce the pleasant aromas and
flavors of many fruits such as bananas,
strawberries, and oranges.
Introduction
• An ester is a carboxylic acid derivative in
which the –OH portion of the carbonyl group
has been replaced with an –OR group.

• The ester functional group is
O
C

O

R
Study Question 2: Saponification
• The principle used in the saponification is
hydrolysis. In amide hydrolysis, the bond
between the carbonyl atom and the nitrogen
is broken, and free acid and free amide are
produced. Amide hydrolysis is catalyzed by
acids, bases, or certain enzymes; also
sustained heating is often required.
Study Question 2: Saponification
• Amide hydrolysis:
• Hydrolysis under Acidic Conditions
• Hydrolysis under Alkaline Conditions
• Acidic or basic hydrolysis conditions have an
effect on the products. Acidic conditions convert
the product amine to amine salt. Basic conditions
convert the product carboxylic acid to carboxylic
acid salt.
Study Question 2: Saponification
• Acidic or basic hydrolysis conditions have an effect on the
products. Acidic conditions convert the product amine to
amine salt. Basic conditions convert the product carboxylic
acid to carboxylic acid salt.
•
Saponification helps differentiate the amides from the
rest of other water-insoluble compounds because the test
reacts on carbonyl atom and nitrogen when carbon is
present in amides.
•
Amides are capable of participating to H-bonding with
water and other priotic solvents; the atom can accept
hydrogen bonds from water and the N-H hydrogen atoms
can donate H-bonds. As a result of interactions such as
these, the water solubility of amides is greater than that of
other hydrocarbons.
ESTERS
• General formula:
PROPERTIES OF ESTERS
– Boiling point: lower than alcohols and carboxylic
acid.
– Cannot form hydrogen bonds because they do not
have a hydrogen atom bonded to an oxygen atom.
– Solubility: rapidly decrease with increasing carbon
chain length
– Most have pleasant odors such as raspberry,
banana, pear, apple and pineapple.
Preparation of Esters
• General formula:

Esters can be prepared through a process called
“Esterification”.
ESTERIFICATION
ESTERIFICATION
• In a reaction called esterification, a
carboxylic acid reacts with an
alcohol when heated in the
presence of an acid catalyst. In the
reaction, water is produced from
the –OH removed from the
carboxylic acid and an –H lost by
the alcohol.
Lab Experiment-Esterification
• Procedure:
• 1. Prepare two clean and dry test tubes. To tube
1, place pinch-amount of salicylic acid and 2.0
ml of methanol. To tube 2, place 2.0 ml of
95% ethanol and 1.0 ml of glacial acetic acid.
Add slowly to both tubes five drops of conc.
Sulfuric acid. (CAUTION: concentrated
sulfuric acid is very corrosive. See first aid
measures in case of accident.) Mix the
contents of both tubes thoroughly.
Lab Experiment- Esterification
• 2. Heat both tubes in a boiling water bath
until the either the odor of the alcohol or
the acid used is no longer obvious. Prepare
two evaporating dishes. In each dish, place
5.0 ml hot water. Pour the contents of test
tubes 1 and 2 separately in the
evaporating dish. Immediately note the
odor of each sample and record your
observations.
RESULTS
SAMPLES

ODORS

1-methanol and salicylic acid smell similar to efficascent oil
2-ethanol and acetic acid

smell similar to a plastic
balloon
Ethanol and Acetic Acid

Methanol and Salicylic Acid (Benzoic
Acid)
• Both samples yield esters into which the –H of
the carboxylic acids (Acetic Acid and Salicylic
Acid) was replaced by an alkyl group.
• In the experiment the –OH group is lost from
the carboxylic acid, a –H atom is lost from the
alcohol and water is formed as a by-product.
The results of this reaction was the
substitution of an –OR group of the alcohol
and for the –OH group of the acid.
Study Question 3
• Aside from amides and carboxylate esters,
what are the other kinds of esters? Give their
equations.
• Methyl Ethanoate

• Ethyl Ethanoate

• Methyl Methanoate
• Ethyl Ethanoate

Study Question 3
• Methyl Methanoate

• Ethyl Methanoate

These are four of the most common kinds of esters.
Study Question 4
• In the formation of esters, why is there a need to
add a small amount of concentrated sulfuric acid?
•
Formation of esters may be achieved through
“esterification”. It is a reaction of a carboxylic acid
and with an alcohol (or phenol) to produce an
ester. In order for esterification to be achieved a
strong catalyst is needed. The Sulfuric Acid
(H2SO4) serves as a catalyst in the process of
esterification which helps increase the chemical
reaction.
Hydrolysis of
Esters
Group 5
Structure of ASA

Figure1: Structure of Acetylsalicylic Acid
Uses
Aspirin is one of the most widely
used drugs in modern society. It is
most frequently used to treat mild to
moderate pain or to reduce fever.
Because of its anti-inflammatory
action, aspirin is prescribed to
individuals who suffer from joint
inflammation conditions such as
rheumatoid
arthritis
and
osteoarthritis.
Hydrolysis of ASA

Figure2: Hydrolysis of Acetylsalicylic Acid
Introduction
Acetylsalicylic Acid
(C6H4OCOCH3COOH) is the ubiquitous

pain reliever known as aspirin.
Chemically, aspirin is both an
aromatic acid and an ester;
analgesic properties not with
standing, the compound is an
excellent showcase for at least two
or three principles of organic
chemistry.
Salicylic Acid
(C6H4OHCOOH; aspirin's parent
compound) and sodium salicylate
(C6H4OHCOONa) are useful for detecting
iron compounds; they form colored
complexes with the Fe3+ ion. They can also
be used in several organic chemistry
experiments which illustrate important
principles.
Ester
Saponification
Acid Hydrolysis
Acid Hydrolysis
“Acid Hydrolysis is the breaking of
the carbon-oxygen single bond
between the “alcohol” part and the
“acid” part. It is also the most
important reaction of esters.”
Acid Hydrolysis
“A carboxylic acid and alcohol are formed
when an ester reacts with water.”
Hydrolysis
“The alkaline hydrolysis of ester
involves reaction with hydroxide
ions. The reaction can either use
water or acid to hydrolyze ester.
Hydrolysis of Ester-General Reaction

O
O
+
ll
ll
H
R-C-O-R’ + H-OH ------> R-C-OH + R’-O-H
Acid Hydrolysis of Methyl Acetate
O
O
+
ll
ll
H
CH3-C-O-CH3 + H-OH -------> CH3-C-OH + CH3-OH
Ester
Saponification
Base Hydrolysis
Base Hydrolysis
“Saponification reaction under basic
conditions, hydrolysis of an organic
compound in which the product is a
carboxylic acid salt. All of the
following go through saponification:
esters, amides, fats and oils.”
Ester Saponification
“A reaction between the ester and a base to
produce a carboxylic acid salt and alcohol. In
this reaction, all carboxylic acid products are
converted to its salt form due to the
conditions of the basic reaction.”
Lab Report-Hydrolysis of Esters
• Acetate Ion (CH3COO-)
• Basic Ferric Acetate Test: Dissolve a small
quantity of CH3COONa in 3 drops of distilled
water. Add 3 drops of 0.5 M FeCl3 solution. If
no color change is observed, add one drop of 6
M nitric acid. Record all observations on the
data sheet.
Lab Report-Hydrolysis of Esters
• Figure 1. Structure of acetylsalicylic acid.
• Aspirin is one of the most widely used drugs in modern society. It is most
frequently used to treat mild to moderate pain or to reduce fever. Because
of its anti-inflammatory action, aspirin is prescribed to individuals who
suffer from joint inflammation conditions such as rheumatoid arthritis and
osteoarthritis.

• Figure 2. Hydrolysis of acetylsalicylic acid to acetic acid and salicylic acid.
Lab Report-Hydrolysis of Esters
PROCEDURE:
D. Hydrolysis of an Ester
Dilute 5.0 ml of 6N sodium hydroxide with an equal volume of water in a
hard glass test tube. Add 5.0 g of acetylsalicylic acid and heat in a boiling
water bath for five minutes. Cool to room temperature and then acidify
the mixture with 6N hydrochloric acid until a precipitate is formed. Filter.
1. Basic Ferric Acetate Test
To 1.0 ml of the filtrate obtained from hydrolysis, add 6N sodium
hydroxide until the solution is slightly alkaline to litmus paper. Add
ferric chloride dropwise to the solution until a change is noted.
Record your observations.
2. Ferric Chloride Test
Mix a pinch of the residue obtained from hydrolysis with 2.0 ml water. Add
three drops of ferric chloride and note what happens. Record your
observation.
Summary of the Hydrolysis of Ester
"The hydrolysis of Ester (ASA/Aspirin) will yield acetic
acid and salicylic acid. Acetic acid, together with the
filtrate, will react to the ferric ion. Acetic acid will be
neutralized and will become Acetate so that Sodium
Hydroxide will be the one reduced and not Acetic
Acid. Acetate will then react with Ferric Chloride,
producing Ferric Acetate which has the visible result
present in the experiment.(reddish brown color)."
Basic Ferric
Acetate Test
Basic Ferric Acetate Test versus Ferric
Chloride Test
• OBJECTIVE
• "The primary objective of Basic Ferric Acetate
Test is to test for any presence of ferric ions
with the use of Ferrous Acetate and the
filtrate. On the other hand, Ferric Chloride
Test is used to test for phenols as residue is
added."
RESULT OF BASIC FERRIC ACETATE TEST
• VISIBLE RESULT
• "An aqueous solution of Basic Ferric Acetate
will yield a reddish brown liquid. The Acetate
from the neutralized Acetic Acid will react
with the Ferric Chloride, producing Ferric
Acetate which is the one responsible for the
visible result in the solution."
Ferric acetate is the coordination
compound more commonly known
as "basic iron acetate". With the
formula [Fe3O(OAc)6(H2O)3]OAc
(OAc is CH3CO2-), it is a salt,
composed of the cation [Fe3(μ3O)(OAc)6(H2O)3]+ and an acetate
anion. The formation of the redbrown complex has long been
used as a test for ferric ions.
Ferric Chloride
Test
The ferric chloride test is used to determine the
presence or absence of phenols in a given
sample. Enols give positive results as well. The
bromine test is useful to confirm the result.
Phenols form a complex with Fe(III), which is
intensely colored. This is the basis for the
test.The sample is dissolved in water, or a
mixture of water and ethanol, and a few drops
of dilute ferric chloride solution is added. The
formation of a red, blue, green, or purple
coloration indicates the presence of phenols.
Where the sample is insoluble in water, it may
be dissolved in dichloromethane with a small
amount of pyridine.
Lab Report-Introduction to the
Ferric Acetate Test
• Acetylsalicylic acid (C6H4OCOCH3COOH) is the ubiquitous pain reliever
known as aspirin. Chemically, aspirin is both an aromatic acid and an
ester; analgesic properties notwithstanding, the compound is an excellent
showcase for at least two or three principles of organic chemistry.
• Salicylic acid (C6H4OHCOOH; aspirin's parent compound) and sodium
salicylate (C6H4OHCOONa) are useful for detecting iron compounds; they
form colored complexes with the Fe3+ ion. They can also be used in several
organic chemistry experiments which illustrate important principles.
• For convenience we may abbreviate acetic acid as HOAc or AcOH. This
refers to an acetate group ("OAc"; Figure 1) with a hydrogen ("H"). Acetic
acid loses an H+ when it ionizes to acetate, which is then abbreviated as
OAc-.
Lab Report-Introduction to the
Ferric Acetate Test
• Because the shorthand system becomes
ambiguous with more complex molecules,
we'll refer to salicylic acid as "SA" and
acetylsalicylic acid as "ASA". (Consider that
HOSal could be salicylic acid, if we assume the
dissociable H+ comes from the carboxylic acid
group.)
Basic Ferric Acetate Test
• Ferric acetate is the coordination compound more commonly known as
"basic iron acetate". With the formula [Fe3O(OAc)6(H2O)3]OAc (OAc is
CH3CO2-), it is a salt, composed of the cation [Fe3(μ3-O)(OAc)6(H2O)3]+
and an acetate anion. The formation of the red-brown complex has long
been used as a test for ferric ions.
•

• Figure 3. Reddish Brown Solution of Basic Ferric Acetate Test
• Laboratory Observation: The solution turned reddish brown in color.
Basic Ferric Acetate Test
• Q: In the basic ferric acetate test, why is it important
that the solution be kept neutral? What would
happen if there is an excess of acid or alkali?
• A: Acetate would either be oxidized or reduced.
Ferric Chloride Test
• The ferric chloride test is used to determine the presence or
absence of phenols in a given sample. Enols give positive
results as well. The bromine test is useful to confirm the result.
Phenols form a complex with Fe(III), which is intensely colored.
This is the basis for the test.The sample is dissolved in water,
or a mixture of water and ethanol, and a few drops of dilute
ferric chloride solution is added. The formation of a red, blue,
green, or purple coloration indicates the presence of phenols.
Where the sample is insoluble in water, it may be dissolved in
dichloromethane with a small amount of pyridine.
Ferric Chloride Test

Figure 4. Purple Solution of Ferric Chloride Test
-----------------------------------------------------------------------------------------------Laboratory Observation: The solution turns purple in color.
Study Question 5
Q: After alkaline hydrolysis of acetylsalicyclic acid and
acidification, what products (filtrate and residue)
are formed? Write the equations involved and
name the corresponding products.
A: The hydrolysis of acetylsalicyclic acid aspirin will
yield acetic acid (residue) and salicylic acid (filtrate).
Study Question 6
Q: What tests proved the identity of the products (filtrate and
residue). Give all equations involved and the formulas
responsible for the visible results.
A: The Ferric Chloride Test proved the identity of the products,
acetic acid and salicylic acid. The Ferric Chloride test showed
the presence of the phenol group –OH both the residue and
the filtrate which proved that the presence that both are
carboxylic acids.
O
Cl
||
|
CH3-C-OH + H2O+ FeCl3 -> FeO(OH) + CH3-C-Cl
|
Cl

Salicylic Acid + FeCl3 -> Iron (III) Salicylate and hydrochloric acid

+ FeCl3 -> Fe(C7H5O3)3 (aq) + 3HCl (aq)
3 C7H6O3 (aq)
Test for Benzoic Acid
Benzoic Acid
Introduction:
• Benzoic acid is the simplest aromatic
carboxylic acid. Its chemical formula is
C7H6O2 (or C6H5COOH).
• Its structure is of a benzene ring (6-sided ring)
and has the following attachment to a carbon
on its ring: a carbonyl group and a hydroxyl
group.
Physical and Chemical Properties of
Benzoic Acid
It’s a colorless, crystalline solid. Its melting point is at
122°C and its boiling point is 249°C.
• Solubility:
• Benzoic acid is soluble in hot water but in room
temperature water (25°C), its solubility is 0.34 g/100
ml, which means it is insoluble.
• It is soluble in ethanol (2.58M), methanol (2.91M).
•
• Chemical Properties
• Benzoic acid: pka = 4.21
Preparation of Benzoic Acid

Uses of Benzoic Acid
Benzoic Acid and its salts are used as
food preservatives. One of the salt
derivatives is the carboxylic acid salt,
benzoate.
Two possible reactions
• From the lab experiment performed, either
one of two reactions can occur:
• The production of a benzamide (if water used
was hot enough) or
• The production of a carboxylic acid salt, a
benzoate
• To coincide with my lab result, I will discuss
the production of a benzoate and thus will
proceed to discuss Carboxylic Acid Salts,
specifically enzoic Acid.
BENZOIC ACID
Introduction
• Benzoic acid is a weak acid, the simplest
aromatic carboxylic acid. Its chemical formula
is C7H6O2 (or C6H5COOH). Its structure is of a
benzene ring and has the following
attachment to a carbon on its ring: a carbonyl
group and a hydroxyl group.
BENZOIC ACID-PHYSICAL AND
CHEMICAL PROPERTIES

Physical Properties of Benzoic Acid
It’s a colorless, crystalline solid. Its melting point is at 122ºC and its boiling point
is 249ºC.

Solubility:
Benzoic acid is soluble in hot water but in room temperature water (25ºC), its
solubility is 0.34 g/100 ml, which means it is basically insoluble or only slightly
soluble in room temperature water. It is soluble in THF (3.37M), ethanol (2.58M),
methanol (2.91M).
Chemical Properties
Benzoic acid: pka = 4.21
BENZOIC ACID
• Preparation of Benzoic Acid
• Commercially, Benzoic acid is produced by the
partial oxidation of toluene with oxygen with
one the following catalysts: manganese
naphthenate or cobalt.
LAB EXPERIMENT- BACKGROUND
• From the lab experiment performed, either
one of two reactions could have occurred if
the right conditions were maintained:
• The production of a benzamide (100°C water
used) and a dehydrating agent was used.
• The production of a carboxylic acid salt, a
benzoate (if the water did not maintain
100°C).
LAB EXPERIMENT-BACKGROUND
As the water was not kept hot enough to
produce an amide, the resulting reaction
produced a benzoate and therefore, I will
proceed only in the discussion of carboxylic
acid salts and the “Test for Benzoic Acid” lab
experiment.
CARBOXYLIC ACID SALTS
• Carboxylic Acid Salt
• A carboxylic acid salt is an ionic compound in
which the negative ion is a carboxylate ion.
- Exploring Organic and Biological
Chemistry
• Carboxylic acid salts are produced from the
neutralization reaction between a carboxylic
acid and a strong base.
LAB REPORT-TEST FOR BENZOIC ACID
•

Lab Report: Test for Benzoic Acid

Objective:
To test for an aromatic acid, in this lab, it is a test for the presence of a benzoic acid
Reagents used:
Benzoic acid
Ammonium Hydroxide (6N NaOH)
Ferric Chloride [Iron (III) Chloride]
•

Materials/Equipment used:
Water bath (hot water)
One test tube
Graduated cylinder
Litmus paper
Reagents used in Lab experiment
Benzoic Acid
O
|| ..
C – OH

Ammonium Hydroxide

Iron (III) Chloride
Ferric (III) Chloride

|

NH4 OH - a Bronsted-Lowry Base
NH3
+ H20 => NH4+ + OHAmmonia Water Ammonium Hydroxide ion
(Base H+ (Acid H+ ion
(basic solution)
Acceptor) Donor)
LAB REPORT-TEST FOR BENZOIC ACID
Procedure:
1) Take 1 test tube and add water (6-7 ml)
2) Heat in a hot water bath and after heating, make
sure there is 5ml of water left for the procedure
3) Dissolve a “mongo-grain” amount of Benzoic Acid
in the 5ml of hot H20
4) Add 6N NH4OH until the solution is neutral or
slightly alkaline (test with litmus paper).
5) If it is alkaline, warm until solution is neutral.
6) Add 6 gtts of FeCl3 and note what is formed.
LAB REPORT-TEST FOR BENZOIC ACID
• Reaction: A benzoate is formed from a
reaction between the weak acid, Benzoic
Acid, and the weak base, Ammonium
Hydroxide (Brönsted-Lowry Base) and the
FeCl3 is used to detect if there is an aromatic
acid. The positive test for benzoic acid using
FeCl3 will be a precipitate of an orange or tan
color.
LAB REPORT-TEST FOR BENZOIC ACID
• Benzoic Acid + Ammonium hydroxide →
Ammonium benzoate + Iron (III) Chloride

+

→3

Cl

→

→ + H2O + FeCl3

+ Fe(OH)3 ↓ + H2O

FERRIC (III) HYDROXIDE IS THE COMPOUND RESPONSIBLE
FOR THE ORANGE PRECIPITATE
LAB REPORT-TEST FOR BENZOIC ACID
• Benzoic acid is not soluble in water as it has a benzene ring and therefore
does not have free protons (hydrogens) to donate as part of a hydrogen
bond. In order to neutralize benzoic acid, ammonium hydroxide is used.
The carboxylic acid salts are solids at room temperature and have high
melting points. Because they are ionic compounds, carboxylic acid salts of
the alkali metals (Li+, Na+, and K+) and NH4+ are usually soluble in water.
•
• The Neutralization reaction between the carboxylic acid, Benzoic acid and
the base, Ammonium hydroxide produces a Carboxylic Acid salt,
Ammonium benzoate. The Iron (III) Chloride was used to produce a
reaction showing the presence of an aromatic acid.
•
• RESULT: My lab experiment yielded a rusty orange or tan precipitate in
turbid solution which proves a positive test for benzoic acid.
•
•
Carboxylic acids grp 5
Carboxylic acids grp 5
Amides
• Amides are derivatives of carboxylic acid in which the
carboxyl –OH group is replaced with an amino group or
a substituted amino group ( NH2, NH, N).
Primary Amide

Secondary Amide

Tertiary Amide

Unsubstituted

Monosubstituted

Disubstituted amides

O
||
R-C-NH2

Two hydrogen atoms bond to
the amide nitrogen atom

O
O
||
R-C-NH-R’

An alkyl (or aryl) group and a
hydrogen atom are bonded to
the amide nitrogen atom

O
O
||
R-C-N-R’
|
R

Two alkyl (or aryl) groups and
no hydrogen atoms are bonded
to the amide nitrogen atoms.
Physical Properties of Amides
• Amides have a lone pair (nonbonding pair) of
electrons which is not vailable for bonding
with H+ ions, as Amines do, thus amides do
not exhibit the same basic properties of
amines.
Benzamide
• A benzamide is a secondary (2°)
amide produced from the
Amidification Reaction (a
Condensation reaction) of a benzoic
acid and a primary amine, or in the
case of the lab, an ammonia.
Carboxylic Acid Salt
• A carboxylic acid salt is an ionic compound in
which the negative ion is a carboxylate ion.
- Exploring Organic and Biological
Chemistry
• Carboxylic acid salts are produced from the
neutralization synthesis reaction between a
carboxylic acid and a strong base.
Lab Report-Test for Benzoic Acid-Part E
Objective:
To test for an aromatic acid, in this lab, it is a test for the presence of a
benzoic acid
Reagents used:
• Benzoic acid
• Ammonium Hydroxide (6N NaOH)
• Iron (III) Chloride
Materials/Equipment used:
• Water bath (hot water)
• One test tube
• Graduated cylinder
• Litmus paper
Lab Experiment-Test for Benzoic Acid
Procedure:
1. Take 1 test tube and add water (6-7 ml)
2. Heat in a hot water bath making sure there is 5ml of water left for
the procedure
3. Dissolve a “mongo-grain” amount of Benzoic Acid in the 5ml of
hot H20
4. Add 6N NH4OH until the solution is neutral or slightly alkaline (test
with litmus paper).
5. If it is alkaline, warm until solution is neutral.
6. Add 6 gtts of FeCl3 and note what is formed.
In the laboratory iron(III) chloride is commonly employed as a
Lewis acid for catalysing reactions such as chlorination of
aromatic compounds and Friedel-Crafts reaction of aromatics.
Two different products can be derived from this lab
experiment depending on the temperature of the
water used. For the purpose of this report, I will
discuss both results.
If hot water (100 °C) water was used during the reaction between the
carboxylic acid and an amine, then an amide will be the product.
Product: Ammonium Benzamide (hot water-100°C)
If room temperature water (25°C) water was used during the reaction,
then this will be an acid-base reaction producing a carboxylic acid
salt.
• Two different products can be produced depending on if the water
used was hot or not:
• Product: Ammonium Benzoate (warm water)
Reactions
• Reaction 1: A benzamide is formed from the
reaction between the Benzoic acid and the
Ammonium Hydroxide and the Iron (III)
Chloride [FeCl3) is used as a catalyzing agent.
catalyzing agent.

Hot H2O (100ºC) and FeCl3
-C-OH

+

NH4OH →

-NH2
O
||
C- NH2

+

+ FeCl3 →

+ FeO(OH) ↓ + H2O
Reactions
• Reaction 2: A benzoate is formed from a reaction
between Benzoic Acid and Ammonium Hydroxide
(Bronsted-Lowry Base) and the FeCl3 is used to
detect if there is an aromatic acid.
• Ferric Chloride Test: For presence of aromatic acid.
warm H2O
-C-OH

NH4OH →

+

C7H9NO2

Benzoic Acid + Ammonium hydroxide → Ammonium benzoate

+

→

+ H2O
Result of Lab Experiment
Yield: A rusty orange precipitate in turbid
solution.
Carboxylic acids grp 5

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Carboxylic acids grp 5

  • 1. Carboxylic Acids and Their Derivatives Lab Performed by 1Nur9-Grp 5 Elias, Jose Emmanuel D. Esperanza, John Ruben A. Flores, Norman Karl Genilla, Jonathan L. Manalo, Michelle C.
  • 2. Carboxylic Acids • INTRODUCTION • Carboxylic acids are weak acids. They have sour or tart taste, produce hydronium ions in water, and neutralizes base. Carboxylic acid reacts with an alcohol to form an ester. In an ester, the –H of the carboxylic acid is replaced by an alkyl group. Aspirin is an ester as well as carboxylic acid. Amines and amides are organic compounds that contain nitrogen. Many nitrogen containing compounds are important to life as components of amino acids, proteins and nucleic acid: DNA and RNA. Many amines that exhibit strong physiological activity are used in medicine as decongestants, anesthetics, and sedatives. Amides are derived from carboxylic acids and amines. In biochemistry, the amide bond is called the peptide bond, which links amino acids in proteins.
  • 3. CARBOXYLIC ACIDS • CARBOXYLIC ACID • In carboxylic acids, the functional group is the carboxyl group, which is combination of the carbonyl group and hydroxyl group. • The carboxyl functional group maybe attached to an alkyl group or an aromatic group. • O • ‖ •  —OH –COOH CO2H C • • You encounter carboxylic acids when you use a vinegar salad dressing, which is a solution of acetic acid and water, or experience the sour taste of citric acid in grapefruit or lemon.
  • 4. Solubility, Effervescence, and Precipitate Formation of Carboxylic Acids and Amines
  • 5. Contents • Results • Explanations – Intermolecular bonding – Chemical equations
  • 6. Results Sample Solubility in H2O + Na2CO3 → Effervescence + HCl → Formation of precipitate Acetic acid Soluble 2 – 3 drops No precipitate in yellow solution Triethylamine Soluble 5 drops Bubbly brown top layer (precipitate) with liquid bottom layer Benzoic acid Insoluble 5 drops, still no effervescence White precipitate on top of colorless liquid
  • 7. Explanations Intermolecular bonding Acetic acid .. O II . . CH3 – C – . . + OH .. .. O H H Acetic acid is soluble in water due to its one – carbon length and three hydrogen bonding possibilities. •Carbonyl oxygen with hydrogen of water •Hydroxyl oxygen with hydrogen of water •Hydroxyl hydrogen with oxygen of water
  • 8. Triethylamine .. CH3 – N – CH3 I CH3 .. .. O H H Triethylamine is slightly soluble in water due to the nitrogen in the amine forming an H – bond with a hydrogen of water. Primary and secondary amines have nitrogen (amine) to hydrogen (water) bonding and hydrogen (amine) to oxygen (water) bonding. But in triethylamine, a tertiary amine, only the nitrogen (amine) to hydrogen (water) bonding is possible.
  • 9. Benzoic acid .. O II .. C – OH + .. .. .. O H H Benzoic acid is insoluble in water for two reasons. •The carboxyl group is bonded to the benzene ring. Benzene is insoluble in water. •There are seven carbons in the benzoic acid molecule. Carboxylic acids with five or more carbons are insoluble in water.
  • 10. Chemical equations Acetic acid CH3COOH + H2O + Na2CO3 → CH3COONa + H2O + CO2↑ Bubbles of carbon dioxide were formed when sodium bicarbonate was added to the acetic acid solution. And, a carboxylic acid salt (sodium acetate) was formed (and dissolved in water). CH3COONa + H2O + HCl → CH3COOH + NaCl + H2O No precipitate was formed after the addition of hydrochloric acid to the sodium acetate solution. Since the products (acetic acid and sodium chloride) were both dissolved in water, no precipitate was formed.
  • 11. Triethylamine 1. (CH3CH2)3N + H2O + Na2CO3 → (CH3CH2)3N + Na2CO3 + H2O + CO2↑ 2. (CH3CH2)3N + Na2CO3 + H2O + HCl → (CH3CH2)3N + H2O + NaCl + CO2↑ The triethylamine remained untouched after the addition of sodium bicarbonate. Instead, the sodium bicarbonate decomposed into sodium carbonate, water, and carbon dioxide (effervescence) (eq. 1). Then, the hydrochloric acid was added, yielding sodium chloride and carbonic acid. Carbonic acid eventually broke down into water and carbon dioxide, thus producing a second batch of effervescence. Once again, the triethylamine was untouched after the addition of hydrochloric acid (eq. 2).
  • 12. 1. C6H5COOH + H20 + NaHCO3 → no reaction 2. C6H5COOH + H20 + NaHCO3 + HCL → C6H5COOH + NaCl + H2O • No bubbles were formed in the benzoic acid solution after the addition of sodium bicarbonate. In fact, benzoic acid is insoluble in water at room temperature, but soluble in water at boiling point (eq. 1). The benzoic acid crystals were seen floating on water surface, even after the addition of hydrochloric acid. Instead, the sodium bicarbonate reacted with hydrochloric acid, producing sodium chloride and carbonic acid, which later broke down into carbon dioxide and more water (eq. 2).
  • 13. Benzoic acid C6H5COOH + H2O + Na2CO3 → no reaction There was no bubble formation after adding sodium bicarbonate since benzoic acid is insoluble in water at room temperature (but soluble at water’s boiling point). C6H5COOH + H2O + Na2CO3 + HCl → C6H5COOH + H2O + NaCl + CO2↑ The white “precipitate” in this chemical reaction (after the addition of sodium bicarbonate and hydrochloric acid) was the insoluble benzoic acid. The only reaction that occurred here was between the added compounds (sodium bicarbonate and hydrochloric acid), which formed sodium chloride, more water, and carbon dioxide effervescence.
  • 14. Study Question 1 for Solubility • Account for the difference in solubility: the carboxylic acids and amines in 1) water and 2) sodium bicarbonate and 3) hydrochloric acid. • Intermolecular bonding and solubility in water • Acetic acid is soluble in water because of the following reasons, besides from its polarity (the carboxyl group provides the acid’s polarity).
  • 15. Study Question 1 for Solubility • It has only two carbons. Aldehydes and ketones with at most four carbons are infinitely soluble in water. • There are three hydrogen bonding possibilities in acetic acid. – Carbonyl oxygen H – bonds with hydrogen of water. – Hydroxyl oxygen H – bonds with hydrogen of water. – Hydroxyl hydrogen H – bonds with oxygen of water.
  • 16. Study Question 1 for Solubility • Trimethylamine is partly soluble in water due to the nitrogen in the amine molecule forms an H – bond with hydrogen of a water molecule. Primary and secondary amines have nitrogen (amine) to hydrogen (water) bonding, as well as hydrogen directly bonded to nitrogen (amine) to oxygen (water) bonding. But in triethylamine, a tertiary amine, only the nitrogen (amine) to hydrogen (water) bonding is possible, because no hydrogen is directly bonded to the nitrogen.
  • 17. Study Question 1 for Solubility • Benzoic acid is insoluble in water at room temperature (but soluble in hot water) for two reasons. • The carboxyl group is bonded to a benzene ring. Benzene is nonpolar and insoluble in water. • There are seven carbons in the benzoic acid, six in the benzene ring plus one carboxyl carbon.
  • 18. Study Question 1 for Solubility • • • • Chemical reactions and equations CH3COOH + H2O + Na2CO3 → CH3COONa + H2O + CO2↑ CH3COONa + H2O + HCl → CH3COOH + NaCl + H2O Addition of sodium bicarbonate (Na2CO3) to the acetic acid solution produced effervescence, carbon dioxide bubbles. Also, a carboxylic acid salt was produced, sodium acetate (eq. 1). Later, hydrochloric acid was added to the sodium acetate solution. This reaction yielded acetic acid and sodium chloride; both products are soluble in water. Thus, no precipitate was formed after adding hydrochloric acid (eq. 2).
  • 19. Study Question 1 for Solubility • (CH3CH2)3N + H2O + NaHCO3 → (CH3CH2)3N + Na2CO3 + H2O + CO2↑ • (CH3CH2)3N + Na2CO3 + H2O + HCl → (CH3CH2)3N + H2O + NaCl + CO2↑ • The triethylamine remained untouched after the addition of sodium bicarbonate. Instead, the sodium bicarbonate decomposed into sodium carbonate, water, and carbon dioxide (effervescence) (eq. 1). Then, the hydrochloric acid was added, yielding sodium chloride and carbonic acid. Carbonic acid eventually broke down into water and carbon dioxide, thus producing a second batch of effervescence. Once again, the triethylamine was untouched after the addition of hydrochloric acid (eq. 2).
  • 20. Study Question 1 for Solubility • C6H5COOH + H2O + NaHCO3 → no reaction • C6H5COOH + H2O + NaHCO3 + HCl → C6H5COOH + NaCl + H2O • No bubbles were formed in the benzoic acid solution after the addition of sodium bicarbonate. In fact, benzoic acid is insoluble in water at room temperature, but soluble in water in hot water (eq. 1). The benzoic acid crystals were seen floating on water surface, even after the addition of hydrochloric acid. Instead, the sodium bicarbonate reacted with hydrochloric acid, producing sodium chloride and carbonic acid, which later broke down into carbon dioxide and more water (eq. 2).
  • 22. AMINES • Amines are considered as derivatives of ammonia (NH3) in which one or more hydrogen atoms is replaced with alkyl or aromatic groups. For example, in methylamine, a methyl group replaces one hydrogen atoms in ammonia. The bonding of two methyl groups gives dimethylamine, and the three methyl groups in trimethylamine replace all the hydrogen atoms in ammonia.
  • 23. CLASSIFICATION OF AMINES • Amines are classified the same way as alcohols by counting the number of carbon atoms directly bonded to a nitrogen atom. In a primary amine, one carbon is bonded to a nitrogen atom. In a secondary amine, two carbons are bonded to the nitrogen atom, and a tertiary amine has three carbon atoms bonded to the nitrogen.
  • 24. AMINES Name Primary Amine Ethylamine Secondary Amine Dietheylamine Tertiary Amine Triethylamine Quaternary Tetraethylammonium Ammonium salt bromide Structure
  • 25. PROPERTIES OF AMINES • Amines have higher boiling points than alkanes of similar mass, but lower than the alcohols. • Because amines contain a polar N—H bond, they form hydrogen bonds. However, nitrogen is not as electronegative as oxygen, which makes the hydrogen bonds in amines weaker. The —NH2 in primary amines can form more hydrogen bonds, which gives them higher boiling points than the secondary amines of the same mass. It is not possible for tertiary amines to hydrogen bond with each other(no N—H bonds), which makes their boiling points much lower and similar to those of alkanes.
  • 26. PROPERTIES OF AMINES • Amines are stonger proton acceptors than oxygencontaining organic compounds such as alcohols and ethers; that is, they are stronger bases than these compounds. A 0.1 M aqueous solution of methylamine has a pH of 11.8 and a 0.1 M of aqueous solution of aniline has a pH of 8.6. these solutions are sufficiently basic to turn red litmus paper blue. Carboxylic acid salts are the only other type of organic compound sufficiently basic to turn red litmus paper red.
  • 27. AMIDES • Amides are derivatives of carboxylic acid in which an amino group replaces the hydroxyl group
  • 28. AMIDATION • An amide is produced in a reaction called amidation, in which a carboxylic acid reacts with ammonia or a primary or secondary amine. A molecule of water is eliminated, and the fragments of the carboxylic acid and amine molecules join to form the amide, much like the formation of ester. Because a hydrogen atom must be lost from the amines, only primary and secondary amines undergo amidation.
  • 29. ACETAMIDE • -unlike other water-insoluble organic substances, saponification of an amide releases ammonia which is very distinct for its pungent and urine like smell. • *red litmus paper turned blue on ACETAMIDE due to the presence of ammonia(weak base) • -nitrogen atom in the molecule has a lone pair making it a proton acceptor
  • 30. BASICITY OF AMINES • Because amines acts as weak bases by accepting protons from water and producing hydroxide ions, their aqueous solutions are basic.
  • 31. PROPERTIES OF AMINES • Most of the K value for amines are less than 10^-3, which means that the equilibrium favored the undissociated amine molecules. Aqueous solutions of amines have basic pH values and turn litmus paper blue.
  • 32. HYDROLYSIS OF AMIDES • The most important reaction of amides is hydrolysis. In amide hydrolysis, the bond between the carbonyl carbon atom and the nitrogen is broken, and free acid and free amine are produced. Amide hydrolysis is catalyzed by acids, bases, or certain enzymes; sustained heating is also often required.
  • 33. HYDROLYSIS OF AMIDES • Acidic or basic hydrolysis conditions have an effect on the products. Acidic conditions convert the product amine to amine salt. Basic conditions convert the product carboxylic acid to a carbxylic acid salt. • (PICTURE COURTESY OF BOOK page 715)
  • 34. HYDROLYSIS OF AMIDES • Amide hydrolisis under basic conditions is also called amide saponification, just as ester hydrolysis under basic conditions is called ester saponification. • (PICTURE COURTESY OF BOOK PAGGE 715)
  • 35. HYDROLYSIS OF AMIDES • Amide bonds are formed by the elimination of water. The reverse reaction called hydrolysis occurs when water is added back to the amide bond to split the molecule. When an acid is used, the hydrolysis products of an amide are the carboxylic acid and the ammonium salt. In base hydrolysis, the amide produces the salt of carboxylic acid and ammonia or amine.
  • 36. HYDROLYSIS OF AMIDES • Of the various acid derivatives, amides are the least reactive toward nucleophilic attack, because the unshared electron pair on the nitrogen is delocalized to the carbonyl carbon through resonance. • Thus, unlike most acyl halides or anhydrides, amides must be heated to boiling with aqueous acid or base in order to hydrolyze them. For a primary amide, the product will be ammonium ion and the acid (for acidic hydrolysis) or ammonia and carboxylate ion (for alkaline hydrolysis). The reaction mechanisms are similar to those for the hydrolysis of other acid derivatives.
  • 37. SAPONIFICATION • Procedure: • 1. Prepare 2 clean and dry text tubes. Place 1.0 triethylamine in tube 1, and pinch-amount of acetamide in tube 2. add 1.0 of dilute 6N NaOH solution to each tube and mix thoroughly. • 2. Heat all 2 tubes in a boiling water bath for two minutes.
  • 38. LAB EXPERIMENT: RESULTS SAMPLE REACTION WITH LITMUS PAPER TRIETHYLAMINE THE RED LITMUS PAPER TURNED BLUE ACETAMIDE THE RED LITMUS PAPER TURNED BLUE
  • 40. ESTERS • An ester is similar to a carboxylic acid, except that the oxygen of the carboxyl group is attached to a carbon and not to hydrogen. In ester, the –H of the carboxylic acid is replaced by an O-akyl (alkoxy) group. Fats known as Triglycerides are esters of glycerol and fatty acids, which are long-chain carboxylic acids. Esters produce the pleasant aromas and flavors of many fruits such as bananas, strawberries, and oranges.
  • 41. Introduction • An ester is a carboxylic acid derivative in which the –OH portion of the carbonyl group has been replaced with an –OR group. • The ester functional group is O C O R
  • 42. Study Question 2: Saponification • The principle used in the saponification is hydrolysis. In amide hydrolysis, the bond between the carbonyl atom and the nitrogen is broken, and free acid and free amide are produced. Amide hydrolysis is catalyzed by acids, bases, or certain enzymes; also sustained heating is often required.
  • 43. Study Question 2: Saponification • Amide hydrolysis: • Hydrolysis under Acidic Conditions • Hydrolysis under Alkaline Conditions • Acidic or basic hydrolysis conditions have an effect on the products. Acidic conditions convert the product amine to amine salt. Basic conditions convert the product carboxylic acid to carboxylic acid salt.
  • 44. Study Question 2: Saponification • Acidic or basic hydrolysis conditions have an effect on the products. Acidic conditions convert the product amine to amine salt. Basic conditions convert the product carboxylic acid to carboxylic acid salt. • Saponification helps differentiate the amides from the rest of other water-insoluble compounds because the test reacts on carbonyl atom and nitrogen when carbon is present in amides. • Amides are capable of participating to H-bonding with water and other priotic solvents; the atom can accept hydrogen bonds from water and the N-H hydrogen atoms can donate H-bonds. As a result of interactions such as these, the water solubility of amides is greater than that of other hydrocarbons.
  • 46. PROPERTIES OF ESTERS – Boiling point: lower than alcohols and carboxylic acid. – Cannot form hydrogen bonds because they do not have a hydrogen atom bonded to an oxygen atom. – Solubility: rapidly decrease with increasing carbon chain length – Most have pleasant odors such as raspberry, banana, pear, apple and pineapple.
  • 47. Preparation of Esters • General formula: Esters can be prepared through a process called “Esterification”.
  • 49. ESTERIFICATION • In a reaction called esterification, a carboxylic acid reacts with an alcohol when heated in the presence of an acid catalyst. In the reaction, water is produced from the –OH removed from the carboxylic acid and an –H lost by the alcohol.
  • 50. Lab Experiment-Esterification • Procedure: • 1. Prepare two clean and dry test tubes. To tube 1, place pinch-amount of salicylic acid and 2.0 ml of methanol. To tube 2, place 2.0 ml of 95% ethanol and 1.0 ml of glacial acetic acid. Add slowly to both tubes five drops of conc. Sulfuric acid. (CAUTION: concentrated sulfuric acid is very corrosive. See first aid measures in case of accident.) Mix the contents of both tubes thoroughly.
  • 51. Lab Experiment- Esterification • 2. Heat both tubes in a boiling water bath until the either the odor of the alcohol or the acid used is no longer obvious. Prepare two evaporating dishes. In each dish, place 5.0 ml hot water. Pour the contents of test tubes 1 and 2 separately in the evaporating dish. Immediately note the odor of each sample and record your observations.
  • 52. RESULTS SAMPLES ODORS 1-methanol and salicylic acid smell similar to efficascent oil 2-ethanol and acetic acid smell similar to a plastic balloon
  • 53. Ethanol and Acetic Acid Methanol and Salicylic Acid (Benzoic Acid)
  • 54. • Both samples yield esters into which the –H of the carboxylic acids (Acetic Acid and Salicylic Acid) was replaced by an alkyl group. • In the experiment the –OH group is lost from the carboxylic acid, a –H atom is lost from the alcohol and water is formed as a by-product. The results of this reaction was the substitution of an –OR group of the alcohol and for the –OH group of the acid.
  • 55. Study Question 3 • Aside from amides and carboxylate esters, what are the other kinds of esters? Give their equations. • Methyl Ethanoate • Ethyl Ethanoate • Methyl Methanoate
  • 56. • Ethyl Ethanoate Study Question 3 • Methyl Methanoate • Ethyl Methanoate These are four of the most common kinds of esters.
  • 57. Study Question 4 • In the formation of esters, why is there a need to add a small amount of concentrated sulfuric acid? • Formation of esters may be achieved through “esterification”. It is a reaction of a carboxylic acid and with an alcohol (or phenol) to produce an ester. In order for esterification to be achieved a strong catalyst is needed. The Sulfuric Acid (H2SO4) serves as a catalyst in the process of esterification which helps increase the chemical reaction.
  • 59. Structure of ASA Figure1: Structure of Acetylsalicylic Acid
  • 60. Uses Aspirin is one of the most widely used drugs in modern society. It is most frequently used to treat mild to moderate pain or to reduce fever. Because of its anti-inflammatory action, aspirin is prescribed to individuals who suffer from joint inflammation conditions such as rheumatoid arthritis and osteoarthritis.
  • 61. Hydrolysis of ASA Figure2: Hydrolysis of Acetylsalicylic Acid
  • 63. Acetylsalicylic Acid (C6H4OCOCH3COOH) is the ubiquitous pain reliever known as aspirin. Chemically, aspirin is both an aromatic acid and an ester; analgesic properties not with standing, the compound is an excellent showcase for at least two or three principles of organic chemistry.
  • 64. Salicylic Acid (C6H4OHCOOH; aspirin's parent compound) and sodium salicylate (C6H4OHCOONa) are useful for detecting iron compounds; they form colored complexes with the Fe3+ ion. They can also be used in several organic chemistry experiments which illustrate important principles.
  • 66. Acid Hydrolysis “Acid Hydrolysis is the breaking of the carbon-oxygen single bond between the “alcohol” part and the “acid” part. It is also the most important reaction of esters.”
  • 67. Acid Hydrolysis “A carboxylic acid and alcohol are formed when an ester reacts with water.”
  • 68. Hydrolysis “The alkaline hydrolysis of ester involves reaction with hydroxide ions. The reaction can either use water or acid to hydrolyze ester.
  • 69. Hydrolysis of Ester-General Reaction O O + ll ll H R-C-O-R’ + H-OH ------> R-C-OH + R’-O-H
  • 70. Acid Hydrolysis of Methyl Acetate O O + ll ll H CH3-C-O-CH3 + H-OH -------> CH3-C-OH + CH3-OH
  • 72. Base Hydrolysis “Saponification reaction under basic conditions, hydrolysis of an organic compound in which the product is a carboxylic acid salt. All of the following go through saponification: esters, amides, fats and oils.”
  • 73. Ester Saponification “A reaction between the ester and a base to produce a carboxylic acid salt and alcohol. In this reaction, all carboxylic acid products are converted to its salt form due to the conditions of the basic reaction.”
  • 74. Lab Report-Hydrolysis of Esters • Acetate Ion (CH3COO-) • Basic Ferric Acetate Test: Dissolve a small quantity of CH3COONa in 3 drops of distilled water. Add 3 drops of 0.5 M FeCl3 solution. If no color change is observed, add one drop of 6 M nitric acid. Record all observations on the data sheet.
  • 75. Lab Report-Hydrolysis of Esters • Figure 1. Structure of acetylsalicylic acid. • Aspirin is one of the most widely used drugs in modern society. It is most frequently used to treat mild to moderate pain or to reduce fever. Because of its anti-inflammatory action, aspirin is prescribed to individuals who suffer from joint inflammation conditions such as rheumatoid arthritis and osteoarthritis. • Figure 2. Hydrolysis of acetylsalicylic acid to acetic acid and salicylic acid.
  • 76. Lab Report-Hydrolysis of Esters PROCEDURE: D. Hydrolysis of an Ester Dilute 5.0 ml of 6N sodium hydroxide with an equal volume of water in a hard glass test tube. Add 5.0 g of acetylsalicylic acid and heat in a boiling water bath for five minutes. Cool to room temperature and then acidify the mixture with 6N hydrochloric acid until a precipitate is formed. Filter. 1. Basic Ferric Acetate Test To 1.0 ml of the filtrate obtained from hydrolysis, add 6N sodium hydroxide until the solution is slightly alkaline to litmus paper. Add ferric chloride dropwise to the solution until a change is noted. Record your observations. 2. Ferric Chloride Test Mix a pinch of the residue obtained from hydrolysis with 2.0 ml water. Add three drops of ferric chloride and note what happens. Record your observation.
  • 77. Summary of the Hydrolysis of Ester "The hydrolysis of Ester (ASA/Aspirin) will yield acetic acid and salicylic acid. Acetic acid, together with the filtrate, will react to the ferric ion. Acetic acid will be neutralized and will become Acetate so that Sodium Hydroxide will be the one reduced and not Acetic Acid. Acetate will then react with Ferric Chloride, producing Ferric Acetate which has the visible result present in the experiment.(reddish brown color)."
  • 79. Basic Ferric Acetate Test versus Ferric Chloride Test • OBJECTIVE • "The primary objective of Basic Ferric Acetate Test is to test for any presence of ferric ions with the use of Ferrous Acetate and the filtrate. On the other hand, Ferric Chloride Test is used to test for phenols as residue is added."
  • 80. RESULT OF BASIC FERRIC ACETATE TEST • VISIBLE RESULT • "An aqueous solution of Basic Ferric Acetate will yield a reddish brown liquid. The Acetate from the neutralized Acetic Acid will react with the Ferric Chloride, producing Ferric Acetate which is the one responsible for the visible result in the solution."
  • 81. Ferric acetate is the coordination compound more commonly known as "basic iron acetate". With the formula [Fe3O(OAc)6(H2O)3]OAc (OAc is CH3CO2-), it is a salt, composed of the cation [Fe3(μ3O)(OAc)6(H2O)3]+ and an acetate anion. The formation of the redbrown complex has long been used as a test for ferric ions.
  • 83. The ferric chloride test is used to determine the presence or absence of phenols in a given sample. Enols give positive results as well. The bromine test is useful to confirm the result. Phenols form a complex with Fe(III), which is intensely colored. This is the basis for the test.The sample is dissolved in water, or a mixture of water and ethanol, and a few drops of dilute ferric chloride solution is added. The formation of a red, blue, green, or purple coloration indicates the presence of phenols. Where the sample is insoluble in water, it may be dissolved in dichloromethane with a small amount of pyridine.
  • 84. Lab Report-Introduction to the Ferric Acetate Test • Acetylsalicylic acid (C6H4OCOCH3COOH) is the ubiquitous pain reliever known as aspirin. Chemically, aspirin is both an aromatic acid and an ester; analgesic properties notwithstanding, the compound is an excellent showcase for at least two or three principles of organic chemistry. • Salicylic acid (C6H4OHCOOH; aspirin's parent compound) and sodium salicylate (C6H4OHCOONa) are useful for detecting iron compounds; they form colored complexes with the Fe3+ ion. They can also be used in several organic chemistry experiments which illustrate important principles. • For convenience we may abbreviate acetic acid as HOAc or AcOH. This refers to an acetate group ("OAc"; Figure 1) with a hydrogen ("H"). Acetic acid loses an H+ when it ionizes to acetate, which is then abbreviated as OAc-.
  • 85. Lab Report-Introduction to the Ferric Acetate Test • Because the shorthand system becomes ambiguous with more complex molecules, we'll refer to salicylic acid as "SA" and acetylsalicylic acid as "ASA". (Consider that HOSal could be salicylic acid, if we assume the dissociable H+ comes from the carboxylic acid group.)
  • 86. Basic Ferric Acetate Test • Ferric acetate is the coordination compound more commonly known as "basic iron acetate". With the formula [Fe3O(OAc)6(H2O)3]OAc (OAc is CH3CO2-), it is a salt, composed of the cation [Fe3(μ3-O)(OAc)6(H2O)3]+ and an acetate anion. The formation of the red-brown complex has long been used as a test for ferric ions. • • Figure 3. Reddish Brown Solution of Basic Ferric Acetate Test • Laboratory Observation: The solution turned reddish brown in color.
  • 87. Basic Ferric Acetate Test • Q: In the basic ferric acetate test, why is it important that the solution be kept neutral? What would happen if there is an excess of acid or alkali? • A: Acetate would either be oxidized or reduced.
  • 88. Ferric Chloride Test • The ferric chloride test is used to determine the presence or absence of phenols in a given sample. Enols give positive results as well. The bromine test is useful to confirm the result. Phenols form a complex with Fe(III), which is intensely colored. This is the basis for the test.The sample is dissolved in water, or a mixture of water and ethanol, and a few drops of dilute ferric chloride solution is added. The formation of a red, blue, green, or purple coloration indicates the presence of phenols. Where the sample is insoluble in water, it may be dissolved in dichloromethane with a small amount of pyridine.
  • 89. Ferric Chloride Test Figure 4. Purple Solution of Ferric Chloride Test -----------------------------------------------------------------------------------------------Laboratory Observation: The solution turns purple in color.
  • 90. Study Question 5 Q: After alkaline hydrolysis of acetylsalicyclic acid and acidification, what products (filtrate and residue) are formed? Write the equations involved and name the corresponding products. A: The hydrolysis of acetylsalicyclic acid aspirin will yield acetic acid (residue) and salicylic acid (filtrate).
  • 91. Study Question 6 Q: What tests proved the identity of the products (filtrate and residue). Give all equations involved and the formulas responsible for the visible results. A: The Ferric Chloride Test proved the identity of the products, acetic acid and salicylic acid. The Ferric Chloride test showed the presence of the phenol group –OH both the residue and the filtrate which proved that the presence that both are carboxylic acids. O Cl || | CH3-C-OH + H2O+ FeCl3 -> FeO(OH) + CH3-C-Cl | Cl Salicylic Acid + FeCl3 -> Iron (III) Salicylate and hydrochloric acid + FeCl3 -> Fe(C7H5O3)3 (aq) + 3HCl (aq) 3 C7H6O3 (aq)
  • 93. Benzoic Acid Introduction: • Benzoic acid is the simplest aromatic carboxylic acid. Its chemical formula is C7H6O2 (or C6H5COOH). • Its structure is of a benzene ring (6-sided ring) and has the following attachment to a carbon on its ring: a carbonyl group and a hydroxyl group.
  • 94. Physical and Chemical Properties of Benzoic Acid It’s a colorless, crystalline solid. Its melting point is at 122°C and its boiling point is 249°C. • Solubility: • Benzoic acid is soluble in hot water but in room temperature water (25°C), its solubility is 0.34 g/100 ml, which means it is insoluble. • It is soluble in ethanol (2.58M), methanol (2.91M). • • Chemical Properties • Benzoic acid: pka = 4.21
  • 95. Preparation of Benzoic Acid Uses of Benzoic Acid Benzoic Acid and its salts are used as food preservatives. One of the salt derivatives is the carboxylic acid salt, benzoate.
  • 96. Two possible reactions • From the lab experiment performed, either one of two reactions can occur: • The production of a benzamide (if water used was hot enough) or • The production of a carboxylic acid salt, a benzoate • To coincide with my lab result, I will discuss the production of a benzoate and thus will proceed to discuss Carboxylic Acid Salts, specifically enzoic Acid.
  • 97. BENZOIC ACID Introduction • Benzoic acid is a weak acid, the simplest aromatic carboxylic acid. Its chemical formula is C7H6O2 (or C6H5COOH). Its structure is of a benzene ring and has the following attachment to a carbon on its ring: a carbonyl group and a hydroxyl group.
  • 98. BENZOIC ACID-PHYSICAL AND CHEMICAL PROPERTIES Physical Properties of Benzoic Acid It’s a colorless, crystalline solid. Its melting point is at 122ºC and its boiling point is 249ºC. Solubility: Benzoic acid is soluble in hot water but in room temperature water (25ºC), its solubility is 0.34 g/100 ml, which means it is basically insoluble or only slightly soluble in room temperature water. It is soluble in THF (3.37M), ethanol (2.58M), methanol (2.91M). Chemical Properties Benzoic acid: pka = 4.21
  • 99. BENZOIC ACID • Preparation of Benzoic Acid • Commercially, Benzoic acid is produced by the partial oxidation of toluene with oxygen with one the following catalysts: manganese naphthenate or cobalt.
  • 100. LAB EXPERIMENT- BACKGROUND • From the lab experiment performed, either one of two reactions could have occurred if the right conditions were maintained: • The production of a benzamide (100°C water used) and a dehydrating agent was used. • The production of a carboxylic acid salt, a benzoate (if the water did not maintain 100°C).
  • 101. LAB EXPERIMENT-BACKGROUND As the water was not kept hot enough to produce an amide, the resulting reaction produced a benzoate and therefore, I will proceed only in the discussion of carboxylic acid salts and the “Test for Benzoic Acid” lab experiment.
  • 102. CARBOXYLIC ACID SALTS • Carboxylic Acid Salt • A carboxylic acid salt is an ionic compound in which the negative ion is a carboxylate ion. - Exploring Organic and Biological Chemistry • Carboxylic acid salts are produced from the neutralization reaction between a carboxylic acid and a strong base.
  • 103. LAB REPORT-TEST FOR BENZOIC ACID • Lab Report: Test for Benzoic Acid Objective: To test for an aromatic acid, in this lab, it is a test for the presence of a benzoic acid Reagents used: Benzoic acid Ammonium Hydroxide (6N NaOH) Ferric Chloride [Iron (III) Chloride] • Materials/Equipment used: Water bath (hot water) One test tube Graduated cylinder Litmus paper
  • 104. Reagents used in Lab experiment Benzoic Acid O || .. C – OH Ammonium Hydroxide Iron (III) Chloride Ferric (III) Chloride | NH4 OH - a Bronsted-Lowry Base NH3 + H20 => NH4+ + OHAmmonia Water Ammonium Hydroxide ion (Base H+ (Acid H+ ion (basic solution) Acceptor) Donor)
  • 105. LAB REPORT-TEST FOR BENZOIC ACID Procedure: 1) Take 1 test tube and add water (6-7 ml) 2) Heat in a hot water bath and after heating, make sure there is 5ml of water left for the procedure 3) Dissolve a “mongo-grain” amount of Benzoic Acid in the 5ml of hot H20 4) Add 6N NH4OH until the solution is neutral or slightly alkaline (test with litmus paper). 5) If it is alkaline, warm until solution is neutral. 6) Add 6 gtts of FeCl3 and note what is formed.
  • 106. LAB REPORT-TEST FOR BENZOIC ACID • Reaction: A benzoate is formed from a reaction between the weak acid, Benzoic Acid, and the weak base, Ammonium Hydroxide (Brönsted-Lowry Base) and the FeCl3 is used to detect if there is an aromatic acid. The positive test for benzoic acid using FeCl3 will be a precipitate of an orange or tan color.
  • 107. LAB REPORT-TEST FOR BENZOIC ACID • Benzoic Acid + Ammonium hydroxide → Ammonium benzoate + Iron (III) Chloride + →3 Cl → → + H2O + FeCl3 + Fe(OH)3 ↓ + H2O FERRIC (III) HYDROXIDE IS THE COMPOUND RESPONSIBLE FOR THE ORANGE PRECIPITATE
  • 108. LAB REPORT-TEST FOR BENZOIC ACID • Benzoic acid is not soluble in water as it has a benzene ring and therefore does not have free protons (hydrogens) to donate as part of a hydrogen bond. In order to neutralize benzoic acid, ammonium hydroxide is used. The carboxylic acid salts are solids at room temperature and have high melting points. Because they are ionic compounds, carboxylic acid salts of the alkali metals (Li+, Na+, and K+) and NH4+ are usually soluble in water. • • The Neutralization reaction between the carboxylic acid, Benzoic acid and the base, Ammonium hydroxide produces a Carboxylic Acid salt, Ammonium benzoate. The Iron (III) Chloride was used to produce a reaction showing the presence of an aromatic acid. • • RESULT: My lab experiment yielded a rusty orange or tan precipitate in turbid solution which proves a positive test for benzoic acid. • •
  • 111. Amides • Amides are derivatives of carboxylic acid in which the carboxyl –OH group is replaced with an amino group or a substituted amino group ( NH2, NH, N). Primary Amide Secondary Amide Tertiary Amide Unsubstituted Monosubstituted Disubstituted amides O || R-C-NH2 Two hydrogen atoms bond to the amide nitrogen atom O O || R-C-NH-R’ An alkyl (or aryl) group and a hydrogen atom are bonded to the amide nitrogen atom O O || R-C-N-R’ | R Two alkyl (or aryl) groups and no hydrogen atoms are bonded to the amide nitrogen atoms.
  • 112. Physical Properties of Amides • Amides have a lone pair (nonbonding pair) of electrons which is not vailable for bonding with H+ ions, as Amines do, thus amides do not exhibit the same basic properties of amines.
  • 113. Benzamide • A benzamide is a secondary (2°) amide produced from the Amidification Reaction (a Condensation reaction) of a benzoic acid and a primary amine, or in the case of the lab, an ammonia.
  • 114. Carboxylic Acid Salt • A carboxylic acid salt is an ionic compound in which the negative ion is a carboxylate ion. - Exploring Organic and Biological Chemistry • Carboxylic acid salts are produced from the neutralization synthesis reaction between a carboxylic acid and a strong base.
  • 115. Lab Report-Test for Benzoic Acid-Part E Objective: To test for an aromatic acid, in this lab, it is a test for the presence of a benzoic acid Reagents used: • Benzoic acid • Ammonium Hydroxide (6N NaOH) • Iron (III) Chloride Materials/Equipment used: • Water bath (hot water) • One test tube • Graduated cylinder • Litmus paper
  • 116. Lab Experiment-Test for Benzoic Acid Procedure: 1. Take 1 test tube and add water (6-7 ml) 2. Heat in a hot water bath making sure there is 5ml of water left for the procedure 3. Dissolve a “mongo-grain” amount of Benzoic Acid in the 5ml of hot H20 4. Add 6N NH4OH until the solution is neutral or slightly alkaline (test with litmus paper). 5. If it is alkaline, warm until solution is neutral. 6. Add 6 gtts of FeCl3 and note what is formed. In the laboratory iron(III) chloride is commonly employed as a Lewis acid for catalysing reactions such as chlorination of aromatic compounds and Friedel-Crafts reaction of aromatics.
  • 117. Two different products can be derived from this lab experiment depending on the temperature of the water used. For the purpose of this report, I will discuss both results. If hot water (100 °C) water was used during the reaction between the carboxylic acid and an amine, then an amide will be the product. Product: Ammonium Benzamide (hot water-100°C) If room temperature water (25°C) water was used during the reaction, then this will be an acid-base reaction producing a carboxylic acid salt. • Two different products can be produced depending on if the water used was hot or not: • Product: Ammonium Benzoate (warm water)
  • 118. Reactions • Reaction 1: A benzamide is formed from the reaction between the Benzoic acid and the Ammonium Hydroxide and the Iron (III) Chloride [FeCl3) is used as a catalyzing agent. catalyzing agent. Hot H2O (100ºC) and FeCl3 -C-OH + NH4OH → -NH2 O || C- NH2 + + FeCl3 → + FeO(OH) ↓ + H2O
  • 119. Reactions • Reaction 2: A benzoate is formed from a reaction between Benzoic Acid and Ammonium Hydroxide (Bronsted-Lowry Base) and the FeCl3 is used to detect if there is an aromatic acid. • Ferric Chloride Test: For presence of aromatic acid. warm H2O -C-OH NH4OH → + C7H9NO2 Benzoic Acid + Ammonium hydroxide → Ammonium benzoate + → + H2O
  • 120. Result of Lab Experiment Yield: A rusty orange precipitate in turbid solution.