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REPUBLIC OF THE PHILIPPINES

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NORTHERN NEGROS STATE COLLEGE OF SCIENCE AND TECHNOLOGY
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OLD SAGAY, SAGAY CITY, NEGROS OCCIDENTAL
(034)722-4169/www.nonescost.edu.com

COLLEGE OF EDUCATION
COURSE MODULE IN

ORGANIC
CHEMISTRY
2nd Semester A.Y.2021–2022
COURSE FACILITATORS: MA. JOSEFA L. FACULTAD, LPT, MAEd
JENEZA M. BANASING, LPT, MEd.
FB/MESSENGER : Marijo Facultad
Jenz Manguilimutan Banasing
Email/Cp No. : facultadmarijo@gmail.com/ O9295225330
jeneza.banasing70@gmail.com/09394417423

2
MODULE
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MODULE
2

LESSON

1 ALDEHYDES AND KETONES

9
HOURS

Aldehydes and ketones are organic compounds which incorporate a carbonyl

functional group, C=O. The carbon atom of this group has two remaining bonds that
may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these
substituents is hydrogen, the compound is an aldehyde. This lesson will give an
overview about the nomenclature, physical and chemical properties, and uses or
applications of aldehydes and ketones.

At the end of the lesson, you are expected to:

1. identify carbonyl groups in aldehydes and ketones
2. distinguish aldehyde or a ketone from other compounds
3. assign IUPAC names to aldehydes and ketones
4. identify hemiacetals and acetals, hemiketals and ketals
5. write reactions of aldehydes and ketones
6. observe the positive and negative impact on the use of these compounds
industry and household

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When human body dies, formalin is used as a preservative. Formalin belongs to the
family of aldehydes having a great importance in industry.

Girls become attractive when their nails are applied with nail polish. But when
nail polish is changed, a liquid called acetone is used. Acetones belong to the ketone
family.

You will remember that the difference between an aldehyde and a ketone is
the presence of a hydrogen atom attached to the carbon-oxygen double bond in the
aldehyde. Ketones don't have that hydrogen. The presence of that hydrogen atom
makes aldehydes very easy to oxidize (i.e., they are strong reducing agents). How
about ketones? Are ketones a reducing agents or oxidizing agents?

If alcohols have -OH functional group, how about aldehydes? Ketones?

Aldehydes and ketones are closely related classes of compounds. Their structure
contains the carbonyl group C=O, a carbon-oxygen double bond.
Aldehydes have at least one hydrogen atom bonded to the carbonyl group,
whereas ketones have only alkyl or aryl (aromatic, denoted Ar) groups bonded to the
carbonyl group.
R-CHO Ar-CHO R-CO-R R-CO-Ar Ar-CO-Ar
Aldehydes Ketones
The general formula for the saturated homologous series of aldehydes and
ketones is C2H2nO

Members of Aldehyde Family

HCHO ---- Formaldehyde --- Methanal

CH3CHO---Acetaldehyde ---- Ethanal
CH3CH2CHO—Propionaldehyde--- Propanal
CH3CH2CH2CHO—Butyraldehyde ---Butanal
CH3CH2CH2CH2CHO Valeraldehyde—Pentanal

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CH3(CH2)3CH2CHO --- Caproaldehyde--- Hexanal

Naming Aldehydes

IUPAC Rules in Naming Aldehydes

1. To establish the parent’s name, select the longest continues chain of carbon atoms
that contains the aldehyde group.

2. The carbons of the parent chain are numbered starting with the aldehyde group.
Since the aldehyde group is at the beginning (or end) of the chain, it is understood to be
number 1.

3. Form the parent aldehyde name by dropping the –e from the corresponding alkane
name and adding the suffix –al.

4. Other groups attached to the parent chain are named and numbered as we have
done before.
Examples:
H-CHO CH3-CHO CH3CH2CHCH2CH2CHO 4-methylhexanal
Methanal Ethanal /
CH3
Common names of some aldehydes are widely used. Common names for the
aliphatic aldehydes are derived from the common names of carboxylic acids. The –ic
acid or the –oic acid ending of the acid name is dropped and is replaced with the suffix
–aldehyde.
Examples:
H-CHO CH3CHO CH3CH2CHO
Formaldehyde acetaldehyde propionaldehyde

Branched chain aldehydes are named as derivatives of straight chain aldehydes.

To indicate the point of attachment, Greek letters such as ά, β, γ, δ etc are used. The ά
Carbon is the carbon that is next to the -CHO group.

For ex.
CH3CH2CHCHO CH3CHCHCHO
/ / /
CH3 CH3 CH3
ά - Methylbutyraldehyde ά, β- dimethylbutyraldehyde

Aromatic aldehydes contain the aldehyde group bonded to an aromatic ring.

These aldehydes are named after the corresponding carboxylic acids.
For example;

CHO CH3 CHO

Benzaldehyde p-tolualdehyde

In dialdehydes, the suffix –dial is added to the corresponding hydrocarbon name.

For example:

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 H-COCH2CH2CHO
1,4- Butanedial

IUPAC RULES for Naming Ketones

1. To establish the parent’s name, select the longest continues chain of carbon atoms
that contains the ketone group.

2. Form the parent’s name by dropping the –e from the corresponding alkane name and
adding the suffix –one.

3. If the chain is longer than four carbon atoms, it is numbered so that the carbonyl
group has the smallest possible number; this number is prefixed to the parent’s name of
the ketone.

4. Other groups attached to the parent chain are named and numbered as we have
done before.

For examples:
CH3-CO-CH3 CH3CH2CH2-CO-CH3 CH3CH2-CO-CHCH2CH3
Propanone 2-pentanone /
Dimethyl ketone methyl propyl ketone CH3
4-methyl-3-hexanone
Ethyl sec- butyl ketone
An alternative non-IUPAC method that is often used to name simple ketones list
the name of the alkyl or aromatic groups attached to the carbonyl carbon together with
the word –ketone:

CH3-CO-CH2CH3 CO-CH3 CO-CH2CH3

ethyl methyl ketone methyl phenyl ketone ethyl phenyl ketone

2-butanone 1-phenylethanone 1-phenyl-1-propanone
Acetophenone

CH3CHCOCH3 C6H5COC6H5
/ Benzophenone
CH3 Diphenyl ketone
Isopropyl methyl ketone
3- methyl-2-butanone

Physical Properties of Aldehydes and Ketones

Unlike alcohols, aldehydes and ketones cannot hydrogen-bond to themselves,

because no hydrogen is attached to the oxygen atom of the carbonyl group.

Aldehydes and ketones have lower boiling points than alcohols of comparable
molar mass.

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 Low-molar mass aldehydes and ketones are soluble in water, but for five or more
carbons, the solubility decreases markedly. Ketones are highly efficient organic
solvents.

Boiling Points of Selected Aldehydes and Ketones

and Corresponding Alcohols
Name Molar mass Boiling point(°C)
1-propanol 60 97
propanal 58 49
propanone 58 56

1-butanol 74 118
butanal 72 76
butanone 72 80

1-pentanol 88 138
pentanal 86 103
2-pentanone 86 102

The lower-molar mass aldehydes have a penetrating, disagreeable odor and are
partially responsible for the taste of some rancid and stale foods. As the molar mass
increases, the odor of both aldehydes and ketones- especially the aromatic ones-
becomes more fragrant. Some are even used in flavorings and perfumes.
Ex are
Benzaldehyde (oil of bitter almonds)
Cinnamaldehyde (chief constituent of oil of cinnamon)
Camphor (from camphor tree); fragrant penetrating odor; has some medicinal
uses: as analgesic, found in some liniments
Citral (oil of lemon grass); major component about 70%
Vanillin (constituent of vanilla bean)
Butyraldehyde – unpleasant odor in rancid butter

Chemical Properties of Aldehydes and Ketones

The characteristic reactions are:

A. Oxidation and reduction reactions

Aldehydes undergo both oxidation and reduction reactions
Ketones undergo reduction reaction only

B. Addition reactions: both aldehydes and ketones undergo addition reactions

Oxidation Reactions

Aldehydes are easily oxidized to carboxylic acids by a variety of oxidizing agents

including (under some conditions) oxygen of the air.

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 A reaction which differs aldehydes from ketones.

- Aldehydes are easily oxidized to carboxylic acids by K2Cr2O7 + H2SO4 and by

mild oxidizing agents such as Ag+ and Cu+2 ions.

Ketones are unaffected by such agents

Ketones can be oxidized under drastic conditions – for ex. By treatment of hot
KMnO4 solution. However, under these conditions C-C bonds are broken and a variety
of products are produced

The following are the reactions for the oxidation of aldehydes

a) by dichromate
3RCHO + Cr2O7-2 + 8H+ → 3RCOOH + 2Cr+3 + 4H2O
Carboxylic acid

3CH3CHO + Cr2O7-2 + 8H+ → 3CH3COOH + 2Cr+3 + 4H2O

Acetaldehyde Acetic acid
Ethanal Ethanoic acid
b) Tollen’s test (silver mirror test) for aldehydes
A test which is based on the ability of the silver ions to oxidized aldehydes
Ag + ions are reduced to metallic Ag

To do it, a little of the suspected aldehyde is added to a solution of silver

nitrate and ammonia in a clean test tube
The appearance of a silver mirror on the inner wall of the tube is a positive test
for the aldehyde group
The general reaction is:
RCHO + 2Ag+ NH3,H2O RCOO-NH4+ + 2Ag(s)
Ammonium salt
Of carboxylic acid
CH3CHO + 2Ag+ NH3,H2O CH3COO-NH4+ + 2Ag(s)
Acetaldehyde Ammonium acetate
Ethanal Ammonium ethanoate

c) Fehling and Benedict tests (the solution contains Cu+2 ions in alkaline
medium)
The aldehyde group is oxidized to an acid by Cu+2 ions
The blue Cu+2 ions are reduced and form brick-red Copper(I)oxide (Cu2O)
which precipitates during reaction
This test is used for detecting carbohydrates that have an available
aldehyde group
The equation is
RCHO + 2Cu+2 NaOH, H2O RCOO-Na+ + Cu2O(solid)
Blue Sodium salt brick-red
Of carboxylic acid
Ketones do not give positive test with Tollens, Fehling or Benedict solutions and
these tests are used to distinguish between ketones and aldehydes
RCOR + Ag+ NH3,H2O no reaction

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 RCOR + Cu+2 NaOH, H2O no reaction

Practice only:
Write structure and names of the organic product (or indicate “no reaction”) for the
following:
a. Pentanal in the Tollen’s test
CH3CH2CH2CH2CHO + 2Ag+ NH3, H2O CH3CH2CH2CH2COONH4 + 2Ag(s)
Pentanal Ammonium Pentanoate
Ammonium Valerate
b. 4- Methyl-2-hexanone in the Tollen’s test
CH3CHCH2CH2COCH3 + 2Ag+ NH3, H2O no reaction
/
CH3
c. 3- Pentanone in the Fehling’s test
CH3CH2COCH2CH3 + Cu+2 NaOH, H2O no reaction

d. 4-Methylhexanal in the Fehling’s test

CH3CH2CHCH2CH2CHO + Cu+2 NaOH, H2O CH3CHCH2CH2CH2COONa
/ /
CH3 CH3
Sodium-4-methylhexanoate
Sodium δ- methylcaproate
Reduction

Aldehydes and ketones are easily reduced to alcohols either elemental hydrogen
in the presence of a catalyst or by chemical reducing agents such as lithium aluminum
hydride (LiAlH4) or sodium borohydride (NaBH4)

Aldehydes yield primary alcohols while ketones yield secondary alcohols

RCHO H2/Ni RCH2OH (1° alcohol)
RCOR H2/Ni RCH(OH)R (°2 alcohol)
Examples
CH3CHO H2/Ni CH3CH2OH
Ethanal Ethanol
CH3COCH3 H2/Ni CH3CH(OH)CH3
Propanone 2-Propanol

Addition Reactions

1. addition of alcohols

Aldehydes and ketones with alcohols form a hemiacetal and hemiketal

Aldehydes react with alcohols in the presence of a trace of acid to form
hemiacetals
Ketones react with alcohols to form hemiketals

Hemiacetals and hemiketals are compounds derived from aldehydes and ketones that
contain an alkoxy and a hydroxyl group on the same carbon atom

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Acetals and ketals are compounds that have 2 alkoxy groups on the same carbon
atom

A hemiacetal has both an alcohol and an ether group attached to the aldehyde carbon
An acetal has two ether groups attached to the aldehyde carbon

A hemiketal is formed if the alcohol and carbonyl groups are within the same carbon
R OH R OH R OR’ R OR
C C C C
H OR’ R OR’ H OR’ R OR’
Hemiacetal Hemiketal Acetal ketal

OH
CH3CH2CHO + CH3OH CH3CH2CH
OCH3
1- Methoxy -1- propanol
(Propionaldehyde methyl hemiacetal)
a hemiacetal
In the presence of excess alcohol and a strong acid such as dry HCl, aldehydes
or hemiacetals react with a second molecule of the alcohol to give acetal

OH OCH3
CH3CH2CH + CH3OH dry HCl CH3CH2CH + H2O
OCH3 OCH3
1- Methoxy-1-propanol
(Propionaldehyde dimethyl acetal)
an acetal
- In a ketone, it gives a hemiketal and a ketal
CH3 OH
CH3COCH3 + CH3OH H+ C + H2O
CH3 OCH3
2- methoxy- 2-propanol
Propanone methyl hemiketal
(a hemiketal)

CH3 OH CH3 OCH3

C + CH3OH dry HCl C + H2O
CH3 OCH3 CH3 OCH3
2-methoxy-2-propanol 2,2- dimethoxy propane
Propanone dimethyl ketal
A ketal

2. addition of hydrogen cyanide

Addition of hydrogen cyanide, HCN to aldehydes and ketones forms
cyanohydrins catalyzed by a small amount of base

Cyanohydrins – have cyano group(-CN) and a hydroxyl group on the same carbon
atom

RCHO or ArCHO + HCN → C-N

/

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 OH
Cyanohydrin

Ex.
CH3CHO + HCN OH- CH3-CH-CN (Acetaldehyde cyanohydrin)
/
OH

CHO + NaCN NaHSO3 -C-CN ( Mandelonitrile)

OH

CH3
/
CH3COCH3 + HCN OH- CH3-C-CN (Acetone cyanohydrin)
/
OH
3. self-addition (aldol condensation)

An aldol condensation refers to an aldehyde or ketone that contains α

hydrogen containing aldehyde or ketone. The product of this reaction contains both a
C=O group and an alcohol group within the same molecule. The reaction is catalyzed by
dilute base.
Ex.
CH3CHO + CH3CHO dilute NaOH CH3-CH-CH2CHO
/
OH
( 3-hydroxybutanal)
An aldol
CH3
/
CH3COCH3 + CH3COCH3 dilute NaOH CH3CCH2COCH3
/
OH
Diacetone alcohol
4-hydroxy-4-methyl-2-pentanone

CH3CH2CHO + CH3CH2CHO dilute NaOH CH3CH2CH-CH-CHO

/ /
OH CH3
3- hydroxyl- 2-methylpentanal
Preparation of Aldehydes and Ketones
A. Preparation of Aldehydes

1. oxidation of primary alcohols

RCH2OH pyridinium RCHO

chlorochromate
Ex.
CH3CH2CH2CH2OH pyridinium CH3CH2CH2CHO
n-Butyl alc. Butanal

2. oxidation of methylbenzenes

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 ArCH3 Cl2, heat ArCHCl2 H2O ArCHO
Ex.

Br CH3 Cl2, heat Br CHCl2 CaCO3,H2O Br r CHO

p-Bromotoulene p- Bromobenzaldehyde

3. reduction of acid chloride

RCOCl or ArCOCl LiAlH RCHO or ArCHO

Ex.

NO2 COCl LiAlH NO2 CHO

p-nitrobenzoyl chloride p-nitrobenzaldehyde

B. Preparation of Ketones
1. oxidation of secondary alcohols
RRCHOH CrO3, K2Cr2O7 RCOR

Ex. CH3 CH3

OH CrO3, K2Cr2O7 O
(CH3)2CH (CH3)2CH
Menthol Menthanone

2. Friedel-Crafts Acylation
RCOCl + ArH AlCl3 RCOAr + HCl
Ex.
nC5H11COCl + AlCl3 nC5H11CO- + HCl

Caproyl chloride n- Pentyl phenyl ketone

Examples of aldehydes and ketones of plant origin:

1. Benzaldehyde (oil of bitter almonds)
2. Cinnamaldehyde (chief constituent of oil of cinnamon)
3. Camphor (from camphor tree); fragrant penetrating odor;has some medicinal
uses: as analgesic, found in
some liniments
4. Citral (oil of lemon grass); major component about 70%
5. Vanillin (constituent of vanilla bean)
6. Butyraldehyde – unpleasant odor in rancid butter

Properties of Some common Aldehydes and keton

1. Formaldehyde (Methanal)
a. Made from methanol by reaction with oxygen(air) in the presence of a Ag or
Cu catalyst
2CH3OH + O2 Ag or Cu 2HCHO + 2H2O
400°C
b. A poisonous irritating gas that is highly soluble in water
c. Marketed as a 37% aqueous solution called formalin which also contains 10-
15% CH3OH to keep formaldehyde from polymerizing

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 d. About 1.33x 109 kg of formaldehyde is produced in the US per year
e. The largest use is in the manufacture of polymers
f. Vapors are intensely irritating to the mucous membranes. Ingestion may cause
severe abdominal pains leading to coma and death
g. In aqueous solution, it has been used to preserve biological specimens, in
fumigation,
H. use to embalm and useful as disinfectant

2. Acetaldehyde (Ethanal)
a. A volatile liquid (boiling point, 21°C) with a pungent, irritating odor
b. Has a general narcotic action and in large doses, may cause respiratory
paralysis
c. Its principal use, is as n intermediate in the manufacture of other chemicals
such as acetic acid and 1-butanol

Acetic acid is made by oxidation of acetaldehyde.

2CH3CHO + O2 Mn+2 CH3COOH
∆
d. It is colorless, water soluble and smells like freshly cut green apples
e. It is use in the manufacture of aniline dyes, synthetic rubber

3. Acetone (Propanone)
a. It is made commercially by fermenting corn or molasses or by
dehydrogenation of 2-propanol
b. A product of destructive distillation of wood
c. A colorless liquid which boils at 56.7°C and possessing a characteristic
pungent odor and a sweet taste
d. A co product in phenol production
e. Produced in the US annually to about 1.26 x 108 kg
f. As a solvent for paint, varnish, fingernail polish remover, cellulose acetate,
acetylene plastics, drugs, chemicals, and smokeless powder
g. formed in the human body as a byproduct of lipid metabolism.
The normal concentration in the body is less than 1mg/100 ml blood
In patients with diabetes milletus, the concentration may rise, and it is then
excreted in the urine were
it can easily be detected. Sometimes the odor can be detected.

Learning Activities 1
Instruction: Give the correct answer as indicated. Each item has corresponding
scores
1. Draw out the structures and give the IUPAC Name for these aldehydes:2 pts
each
A. (CH3)2CH2CHO
B. CHOCH2CH2CHO

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 C. C6H5CH=CHCHO
D. CH3CH(OH)CH2CHO
E. (CH3)3CCH2CH(CH3)CHO
2. Draw out the structures and give IUPAC names of these ketones: 2 pts each
A. (CH3)2C(OH)CH2COCH3
B. CH3COC(CH3)3
C. CH3COCH2CH2COCH3
D. C6H5CH2COCH(CH3)2
E. CH3CH2CH2COC(CH3)3
3. Write equations to show how the following compounds are oxidized by K2Cr2O7
+ H2SO4
A. 3-pentanol
B. 3-ethyl-1-hexanol
C. 2,3-dimethyl-2-butanol

Assessment 1. All answers should be handwritten and must be placed in a bond

paper.

Instruction: In a piece of paper, answer the following questions. Each has

corresponding scores.

1. Give the structural formulas for (2 pts each)

A. 1,3-dichloropropanone
B. 3-butenal
C. 4-phenyl-3-heaxanone
D. 3-ethyl-2-pentanone
E. 3-hydroxypropanal
2. Which compound in each of the following pairs has the higher boiling point? (5
pts)
A. 2-hexanone or 2,5-hexadione
B. Hexane or hexanal
C. 2-pentanone or 2-pentanol
D. Propanone or butanone
E. 1-butanol or butanal
3. Give the structural formula for the organic product from each of the following
reactions? (6 pts)
A. CH3CH2CHO + K2Cr2O7 + H2SO4 →
B. CH3CHCHO + 2Cu+2 OH-
/ H2O
CH3
C. CH3CHCHO + 2Ag+ NH3
/ H2O
CH3
4. Give the products for the reaction of the following compounds with Tollen’s
reagent: (4pts)

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 A. Butanal
B. Methyl ethyl ketone
5. Give the products for the reaction of the following compounds with Benedict’s
reagent (4 pts)
A. Propanal
B. Acetone

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LESSON

2 CARBOXYLIC ACIDS
6
HOURS

A carboxylic acid is an organic compound that contains a carboxyl group

(COOH) attached to an R-group. The general formula of a carboxylic acid is R–COOH,
with R referring to the alkyl group. Carboxylic acids occur widely. Important examples
include the amino acids and fatty acids. This lesson will give information about how
carboxylic acids are named, what properties they possess physically and chemically
and how are they used by the industry and at home.

At the end of the module, you are expected to:

1. Identify the functional group and general structure of a carboxylic acid

2. Identify and name different types of carboxylic acids using classic and IUPAC
nomenclature
3. Describe and explain the general properties of carboxylic acids, including
drawing a comparison with the equivalent alcohol,
4. Describe the preparation of carboxylic acids,
5. Identify and describe the uses of some carboxylic acids found in our daily lives

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 Try to look for a red ant and place it in your skin. Do you know that when you are
bitten by an ant produces carboxylic acids? Goats, palm trees, coconut trees, lauryl
plant and many more are great sources of carboxylic acids.

Carboxylic acids are abundant in plants and animals, but first we should start first
knowing its characteristics.

Carboxylic acids are organic compounds that shows appreciable acidity and
contains the carboxyl group (COOH) attached to either an alky group or an aryl group.

` The taste of vinegar, the sting of an ant, the rancid smell of butter, and the relief
derived from aspirin or ibuprofen- all of these are due to carboxylic acids.

The general formula maybe RCOOH or ArCOOH

Nomenclature of Carboxylic acids

A. Common Names

Because of the abundance in nature, they were among the earliest classes of
compounds studied by organic chemists

It is not surprising that many of these have common names. These names
usually come from some Latin or Greek word that indicates the original source of an
acid

Aliphatic Carboxylic Acids

Carbon Formula Source Common IUPAC Name

atoms Name
1 HCOOH Ants(Latin, formica) Formic acid Methanoic acid
2 CH3COOH Vinegar(Latin,acetum) Acetic acid Ethanoic acid

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 3 CH3CH2COOH Milk(protos pion,first Propionic Propanoic acid
fat) acid
4 CH3(CH2)2COOH Butter(Latin,butyrum) Butyric acid Butanoic acid
5 CH3(CH2)3COOH Valerian Valeric acid Pentanoic acid
root(Latin,valere, to be
strong)
6 CH3(CH2)4COOH Goats(Latin, caper) Caproic Hexanoic acid
acid
7 CH3(CH2)5COOH Vine Enanthic Heptanoic acid
blossom(Greek,oenant acid
he)
8 CH3(CH2)6COOH Goats(Latin, caper) Caprylic Octanoic acid
acid
9 CH3(CH2)7COOH Pelargonium(an herb Pelargonic Nonanoic acid
with stork-shape seed acid
capsules; Greek
pelargos,stork
10 CH3(CH2)8COOH Goats(Latin, caper) Capric acid Decanoic acid
11 CH3(CH2)9COOH Undecanoic acid
12 CH3(CH2)10COOH Lauric acid Dodecanoic acid
13 CH3(CH2)11COOH Tridecanoic acid
14 CH3(CH2)12COOH Myristic Tetradecanoic
acid acid
15 CH3(CH2)13COOH Pentadecanoic
acid
16 CH3(CH2)14COOH Palmitic Hexadecanoic
acid acid
17 CH3(CH2)15COOH Heptadecanoic
acid
18 CH3(CH2)16COOH Stearic Octadecanoic
acid acid
19 CH3(CH2)17COOH Nonadecanoic
acid
20 CH3(CH2)18COOH Arachido Iecosanoic acid
Nic acid

Branched-chain acids and substituted acids are named as derivatives of straight-

chain acids. To indicate the position of attachment, the Greek letters α ,β, ɣ,ɚ are used.
The α carbon is the one bearing the –COOH group.
Ex. CH3-CH2-CH-COOH CH3-CH2-CH-CH-COOH
/ / /
CH3 CH3 CH3
α- Methylbutyric acid α,β-Dimethylvaleric acid

CH2CH2CH2COOH CH2-CH2-CH-COOH CH3-CH-COOH

/ / /
ɣ-Phenylbutyric acid Cl CH3 OH

ɣ-Chloro-α-methylbutyric acid Lactic acid or α-Hydroxypropionic acid

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 Aromatic acids are usually named as derivatives of the parent acid, the Benzoic
acid, the methylbenzoic acids are given the special name of Toluic acids. Ex.
Br COCOOH NO2 COOH
2 CH3 COOH
NO2
p-Bromobenzoic acid 2,4 Dinitrobenzoic acid p-Toluic acid

B. IUPAC NAMES

The IUPAC names follow the usual pattern.

The longest chain carrying the –COOH group is considered the parent structure
and is named by replacing the –e- of the corresponding alkane name by – oic acid.
The position of the substituent is indicated as usual by a number

Ex. CH3CH2CH2CH2COOH CH3CH2CHCOOH CH2CH2COOH

Pentanoic acid / 3- Phenylpropanoic acid
CH3
2-Methylbutanoic acid
CH3CH=CHCOOH
2-Butenoic acid

The name of the salt of a carboxylic acid consists of the name of the cation (Na,
K, NH4, etc.) followed by the name of the acid with the ending –ic acid change to –ate-
Ex.
COONa (CH3COO)2Ca HCOONH4
Sodium benzoate Calcium acetate Ammonium formate
Calcium ethanoate Ammonium methanoate

CH2-CH-COOK
/ /
Br Br
Potassium- α,β-dibromopropionate
Potassium-2,3-dibromopropanoate

In a carboxylic containing alcohol, aldehyde or ketone, the carboxyl group has

priority over alcohol, aldehyde or ketone functionality in naming. The prefix –oxo- is
used to locate the carbonyl group of the aldehyde or ketone;
Ex. HCO-CH2COOH CH3COCH2CHCOOH
3- Oxopropanoic acid /
Br
2-Bromo-4-oxopentanoic acid

Classification of Carboxylic acids

1. Unsaturated carboxylic acids

Contains one or more C=C double bonds
Acrylic acid or Propenoic acid, CH2=CHCOOH,is the first member of the family of
unsaturated carboxylic acids that contains one C=C.
Acrylates, is one of the derivatives of acrylic acid used to manufacture textiles,
paints and lacquers
Oleic acid, CH3(CH2)7CH=CH(CH2)7COOH is another member, a fat constituent

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2. Aromatic Carboxylic acids
A carboxylic acid in which the carbon of the carbonyl group is attached directly to
a carbon in the aromatic ring
Benzoic acid is the parent compound of this series. It is a colorless crystalline
solid occurs in cranberries and coal tar
Sodium benzoate, use to preserve foods such as tomato ketchup and fruit juices
Another examples are the three isomeric Toluic acids

3. Dicarboxylic acids
Carboxylic acids containing two –COOH groups
Oxalic is the simplest member of the aliphatic series;

Members of the Series

Common Name IUPAC Name Formula Source

Oxalic acid Ethanedioic acid HOOC-COOH plants of the oxalic family(ex.
Sorrel)
Malonic acid Propanedioic acid HOOC-CH2-COOH apple(Greek, malon)
Succinic acid Butanedioic acid HOOC-(CH2)2-COOH
amber(Greek,succinum)
Glutaric acid Pentanedioic acid HOOC-(CH2)3-COOH gluten
Adipic acid Hexanedioic acid HOOC-(CH2)4-COOH fat(adeps)
Pimelec acid Heptanedioic acid HOOC-(CH2)5-COOH fat(Greek, pimele)

Oxalic acid
present n spinach in addition to very important vitamins
colorless crystalline solid
concentrated form is poisonous
Malonic acid
biological precursor for the synthesis of fatty acids
Succinic acid
distillation product of amber

Citric acid
a tricarboxylic acid, widely distributed in plants and animal tissue especially in
citrus fruits
(Lemon juice contains 5-8%)
Adipic acid
most important commercial dicarboxylic acid
made from benzene by converting it first to cyclohexene and then by oxidation to
adipic acid
about 8.2 x 108 kg is produced in the US annually
used mostly to produce nylon, also in polyurethane foams, Plasticizers and
lubricating oil additives

Aromatic dicarboxylic acids

contains 2 –COOH groups attached directly to an aromatic ring. Examples are
the 3 isomeric phthalic acids

4. Hydroxy acids

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 Has both the functional groups of a carboxylic acid and an alcohol. Ex. Lactic
acid – found in sour milk, yogurt pickle
Product when our muscles use glucose for energy in the absence of oxygen, a
process called glycolysis Also called α-hydroxypropionic acid
Salicylic acid
has both a carboxylic acid and a phenol
also called o-Hydroxybenzoic acid
use to prepare aspirin
Salicylates
a derivative which is a useful drug which include aspirin, function as analgesic
(pain reliever) antipyretic(fever reducer)
COOH COOCH3
OH + CH3-CO-O-CO-CH3 → COOH + CH3COOH
Acetic
Salicylic acid anhydride Aspirin

Aspirin
good pain reliever
reduces fever and swelling caused by injuries and rheumatism
most impt drug in the treatment of arthritis
Side effects: prevent synthesis of stomach mucus leading to ulceration by
stomach acid of the unprotected stomach walls
Other examples are:
Malic acid – HOOC-CH(OH)-CH2-COOH
Tartaric acid – HOOC-CH(OH)-CH(OH)-COOH or 2,3 Dihydroxybutanedioic

5. Amino acids R-CH-COOH

/
NH2
Has carboxyl group that acts as an acid and amino group that acts as a base
There are 20 biologically important amino acids found in nature
Complicated protein molecules found in every form of life are built from amino
acids
Some protein molecules contain more than 10,000 amino acid units

Physical Properties of Carboxylic acids

1. The first four members(formic-butyric) of the carboxylic acid series are colorless
liquids, completely miscible with water and have sharp unpleasant odors.
Acetic acid, which constitutes about 4-5% of vinegar, provides the characteristic
odor and flavor.
Pure acetic acid (melting point, 16.1°C) solidifies to an icy looking mass when
cooled slightly below normal room temperature and is often called glacial acetic acid
Butyric acid gives rancid butter its disagreeable odor
Goat acids (caproic, caprylic and capric) smell like goats
3-Methyl-2-hexenoic acid, produced by bacteria is responsible for the offensive
odor of human armpits

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2. They have high boiling points for their molecular weights- higher even than those of
comparable alcohols. For ex. Acetic acid and propyl alcohol, which have the same
formula weights(60g/mol), boil at 118°C and 97° respectively

Chemical Properties of Carboxylic acids

1. Acid-base reactions – ability to form hydrogen ions in solution

RCOOH + NaOH → RCOONa + H2O
CH3(CH2)16COOH + NaOH → CH3(CH2)16COONa + H2O
Stearic acid Sodium stearate

2. Salt formation
2RCOOH + M → (RCOO)2M + H2
2CH3COOH + Zn → (CH3COO)2Zn + H2
Zinc acetate

3. Acid chloride formation(RCOCl)

RCOOH + SOCl2 → RCOCl + SO2 + HCl
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl
Acetyl chloride

4. Acid anhydride formation(RCOOCOR’)

RCOCl + M-O-OCR’ → RCO-O-CO-R’ + MCl
CH3COCl + Na-O-OCCH3 → CH3CO-O-CO-CH3 + NaCl
Acetyl chloride Sodium acetate Acetic anhydride

5. Ester formation
Ester – an organic compound formed by the reaction of an acid with an alcohol or
phenol; water is also a product of the reaction
RCOOH + ROH RCOOR’ + H2O

HCOOH + CH3CH2OH HCOOCH2CH3 + H2O

Formic acid Ethyl alc. Ethyl formate
Methanoic acid Ethanol Ethyl methanoate

Esterification is the forward reaction

Hydrolysis is the backward reaction

Preparation of Carboxylic acids

1. Oxidation of primary alcohols or aldehydes
RCH2OH KMnO4, or CrO3 or HNO3 RCOOH
RCHO Ag2O RCOOH
Ex.
CH3(CH2)6CH2OH Jones’rgt CH3(CH2)6COOH
1- Octanol Octanoic acid
CH3(CH2)5CHO Jones’rgt,CrO3,H+ CH3(CH2)5COOH
Heptanal Heptanoic acid
2. Oxidation of alkyl groups attached to aromatic rings
Ex
CH3 KMnO4, heat COOH

Toluene Benzoic acid

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 CH3 CH3 O2, Co(III),CH3COOH COOH COOH

p-Xylene terephthalic acid

CH2CH3 NaMnO4, NaOH ∆ COONa + CO2

Ethyl benzene Sodium benzoate

3. Hyrolysis of cyanides (nitriles)
RCN + 2H2O HCl RCOOH + NH4Cl
RCN + 2H2O NaOH RCOONa + NH3
Ex.
CH3CN + 2H2O H+ CH3COOH + NH4Cl
Methyl nitrile Acetic acid
Ethanoic acid
CH3CN + 2H2O NaOH CH3COONa + NH3
Sodium acetate
Sodium ethanoate

Learning Activities 2
Instruction. Correctly answer the following. Each has corresponding
scores

1. Name the following compounds by IUPAC System: 2 pts each

A. CH3CH2CH2CH(OH)CH2COOH
B. CH3CH2CH(Cl)CH2COONa+ (draw out)
C. C6H5COOK
D. (CH3)3CCH2CH2CH=CHCH2COOH
E. CH3CH(CH3)CH2CH(CH3)CH2COONH4+ (draw out)
2. Draw out the correct structural formula and give the Common name of the ff
acids: 2 pts each
A. CH3(CH2)7CH=CH(CH2)7COOH
B. CH3CH2CH2CH2COONH4+
C. CH3CH(CH3)CH(CH3)CH(CH3)COOH
D. (CH3)3CCH2CH(Cl)COONa+
E. C6H5CH2CH2CH2COOH
g

Assessment 2. All answers should be handwritten and must be placed in a

bond paper

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 Instruction: Use a piece of paper for your answer. Each number has
corresponding scores.

1. Write structures for the following: (2 pts each)

A. 2-chloropropanoic acid
B. Potassium butyrate
C. Sodium p-aminobenzoate
D. Ammonium propanoate
E. Β-hydroxybutyric acid
2. Write the structural formula and IUPAC name of the principal organic product
for the following reactions: (2 pts each)
A. CH3(CH2)7CH=CH(CH2)7COOH + H2 Ni

B. CHO
Na2Cr2O7
H2SO4
C. CH3CH2COOH + NaOH

D. CH2CH2CH3
NaMnO4/NaOH
Δ
E. CH3(CH2)3CH2COOCH2CH2CH3 + NaOH Δ

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LESSON

3 ESTERS
6
HOURS

An ester is a chemical compound derived from an acid (organic or inorganic) in

which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.
Usually, esters are derived from substitution reaction of a carboxylic acid and an
alcohol. This lesson will give you knowledge about esters their nomenclature, physical
and chemical properties and how industries used them in their production.

At the end of the module, you are expected to:

1. assign common names and IUPAC names to esters
2. write the structure of polyester formed from a diol and a dicarboxylic acid
3. establish awareness on the industrial and household application of these
organic compounds

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 Think of some branded candies, juices, perfumes, and some beauty
products. How do they smell? How do esters smell like? Are they dangerous?

Most of the volatile esters have characteristic odor that is why they are used in
synthetic flavors, cosmetics, and perfumes. Isn’t it amazing? But let us focus on its side
effects. Are they safe as flavorings?

Organic compounds with a general formula of RCOOR

Esters are organic compounds formed by the reaction of carboxylic acid with an
alcohol or a phenol; water is also a product in this reaction
RCOOH + R’OH H+ RCO-OR’ + H2O

Carboxylic Alcohol Ester

Acid R can be H, alkyl or aryl, but R’ cannot be H

HCOOH + CH3CH2OH H+ HCO-OCH2CH3 + H2O

Formic acid Ethyl alcohol Ethyl formate

Methanoic acid Ethyl methanoate
This look likes the familiar acid-base reactions called neutralization, but that is
not the case, because the alcohol does not yield OH- ions, and the ester, unlike a salt, is
a molecular, not an ionic substance.

The forward reaction of an acid and an alcohol is called esterification and the
reverse reaction of an ester with water is hydrolysis.

Esterification is one of the most important reactions of carboxylic acids

NOMENCLATURE OF ESTERS

The general formula for an ester is RCOOR’, where R maybe a hydrogen, an

alkyl group, or an aryl group and R’ may be an alkyl group or an aryl group but not a
hydrogen.
Esters are found throughout the nature. The ester linkage is particularly important
in the study of fats and oils, both of which are esters.

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1. Esters are alcohol derivatives of carboxylic acids. They are named in much the same
way as salts.

2. The alcohol part is named first followed by the name of the acid modified to end in –
ate. The –ic ending of the organic acid name is replaced by the ending –ate-. Thus, in
the IUPAC System, ethanoic acid becomes ethanoate. In the common names, acetic
acid becomes acetate.

3. To name an ester, it is necessary to recognize the portion of ester molecule that

comes from the acid, and the portion that comes from the alcohol.

4. In the general formula for an ester, the RCO comes from the acid, and OR’ comes
from the alcohol.

Acid part RCO-OR’ alcohol part

Ethanoate CH3CO-OCH3 Methyl
ester name: methyl ethanoate
methyl acetate

5. The R’ in the R’O is named first followed by the name of the acid, modified by
replacing – ic acid with –ate. The ester derived from ethyl alcohol and acetic acid is
called ethyl acetate or ethyl ethanoate.
Consider the ester derived from CH3CH2COOH and CH3OH:

CH3CH2COOH + CH3OH H+ CH3CH2CO-OCH3 + H2O

Propanoic acid Methanol Methyl propanoate

Propionic acid Methyl alc Methyl propionate

6. Esters of aromatic acids are named in the same way as those of aliphatic acids. For
ex. The ester of benzoic acid and isopropyl alc is C6H5CO-OCH(CH3)2 Isopropyl
benzoate

FORMULA IUPAC NAME COMMON ODOR OR

NAME FLAVOR
CH3CO-OCH2CH2CH(CH3)2 Isopentyl Isoamyl Banana, pear
ethanoate acetate
CH3CH2CH2CO-OCH2CH3 Ethyl butanoate Ethyl butyrate Pineapple
HCO-OCH2CH(CH3)2 Isobutyl Isobutyl Raspberry
methanoate formate
CH3CO-OCH2(CH2)6CH3 Octyl ethanoate Octyl acetate Orange
COOCH3
2-Hydroxy Methyl Wintergreen
OH methylbenzoate salicylate

OCCURRENCE AND PHYSICAL PROPERTIES OF ESTERS

The number of esters that are theoretically possible is very large since many
acids and alcohols are known. Both natural and synthesized esters exist in almost
endless varieties. Some properties of esters are:

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 1. Simple esters derived from monocarboxylic acids and monohydroxy alcohols
are colorless liquids or solids.
2. Low and intermediate molar- mass esters` (from both acids and alcohols up to
about 10 carbon atoms) are liquids with characteristic (usually fragrant or fruity) odors.
The distinctive odor and flavor of many fruits are cause by some one or more of these
esters. For ex., ethyl butyrate has the odor of pineapple, methyl butyrate has the odor of
rum.
3. Esters are used as flavorings and scenting agents.
4. They are generally good solvents for organic substances, and these with
relatively low molar masses are volatile.
5. Esters such as ethyl acetate, butyl acetate, and isoamyl acetate are used
extensively in paints, varnishes, and lacquers.
6. High molar-mass esters (formed from acids and alcohols of 16 or more carbons) are waxes
and are obtained from various plants. They are used in furniture plants. They are used in furniture wax
and automobile wax preparations. For ex., carnauba wax contains esters of 24 and 28 – carbon fatty
acids and 32 and 34 – carbon alcohols.
7. Polyesters with very high molar-masses such as Dacron, are widely used in textile industries.
They are joined by ester linkages between carboxylic acid and alcohol groups.
Diacid + Diol → Polyester
HOOC(CH2)xCOOH HO(CH2)yOH → -OC(CH2)x –CO-O(CH2)y O-

CHEMICAL PROPERTIES OF ESTERS

The most important reaction of esters is hydrolysis – the splitting of molecules

through the addition of water.

Most organic and biochemical substances react only very slowly with water. To
increase the rate of these reactions, a catalyst is required.

In the laboratory, chemists often employ an acid or base as a catalyst for

hydrolysis. In living systems, enzymes act as catalyst.

1. Acid hydrolysis

A reaction of ester with water to form a carboxylic acid and an alcohol. The
hydrolysis is catalyzed by strong acids (H2SO4 or HCl) or by certain enzymes

RCO-OR’ + H2O H+ or enzyme RCOOH + R’OH

CH3CH2CO-OCH3 + H2O H+ or enzyme CH3CH2COOH + CH3OH

Methyl propanoate Propanoic acid Methanol

COOCH3 + H2O H+ or enzyme COOH + CH3OH

OH OH
Methyl salicylate Salicylic acid Methanol

2. Alkaline hydrolysis

It is also called saponification

A hydrolysis of ester by strong base(NaOH or KOH) to produce an alcohol and
a salt( or soap if the salt formed is from a high molar-mass acid)

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 RCO-OR’ + NaOH H2O,∆ RCOO-Na+ + R’OH
Salt Alcohol

CH3(CH2)16CO-OCH2CH3 + NaOH H2O,∆ CH3(CH2)16COONa + CH3CH2OH

Ethyl stearate Sodium stearate Ethanol

The carboxylic acid may be obtained by reacting the salt with a strong acid:
CH3(CH2)16COONa + HCl → CH3(CH2)16COOH + NaCl
Stearic acid

In saponification, the base is a reactant, not a catalyst

Write the complete reaction for the acidic and basic hydrolysis of an ester, isopropyl
butyrate.
1. acidic hydrolysis
CH3CH2CH2COOCHCH3 + H2O H+ CH3CH2CH2COOH + CH3CHCH3
/ /
CH3 OH
2. basic hydrolysis
CH3CH2CH2COOH + NaOH H2O,▲ CH3CH2CH2COONa + CH3CHCH3
/
OH
Fats and oils

They are esters of glycerol and predominantly long-chain fatty acids

Also called triacylglycerols or triglycerides
Each molecule is derived from one molecule of Glycerol and three molecules of
fatty acids
CH2 – O- CO-R CH2 - O- CO-C17H35(stearic acid)
/ /
CH - O- CO-R’ CH - O- CO-C15H31(palmitic acid)
/ /
CH2 –O- CO-R” CH2 - O- CO-C11H23(lauric acid)

General formula for Typical triacylglycerol containing 3 different fatty acids

A triacylglycerol

The most abundant fatty acids in fats and oils are:

1. lauric acid
2. myristic acid
3. palmitic acid
4. stearic acid

The most abundant unsaturated fatty acids in fats and oils contain 18 carbon atoms and
have one, two or three carbon-carbon double bonds:
1. Oleic acid CH3(CH2)7CH=CH(CH2)7COOH
2. Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
3. Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH

The major physical difference between fats and oils is that; fats are solid, and
oils are liquid at room temperature.

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 The glycerol part of the structure is the same for a fat and oil, the difference must
be due to the fatty acid end of the molecule.

Fats contain a large proportion of saturated fatty acids, whereas oils contain
greater amount of unsaturated fatty acids

The term polyunsaturated means that each molecule of fat in a particular

product contains several double bonds.

Fats and oils are obtained from natural sources. Fats come from animal sources
and oils from vegetable sources.

For example:
1. Lard is obtained from hogs, tallow from sheep and cattle.
2. Olive, cottonseed, corn, peanut, soybean,
3. soybean, canola, linseed, and other oils are obtained from the fruit or seed of
their respective vegetable sources

V Assessment: Practice only:

Learning Activities 3
Instruction. Correctly answer the following. Each item has corresponding
scores
1. Give the common names and IUPAC names of the following esters: 2 pts
each
A. CH3CH2CO-OCH2CH3
B. CH3CH2CH2CO-OCH2CH3
C. CH3CH2CO-OCH2CH3
D. C6H5CO-OCH2CH2CH3
E. CH2=CHCO-OCH3
2. Write the condensed structural formula and IUPAC name of the principal
organic product for the following reactions: 8 pts
A. CH3(CH2)3CH2CO-OCH2CH2CH3 + NaOH ▲
B. C6H5CO-OC6H5 + H2O H+ or enzyme

Assessment 3. All answers should be handwritten and must be placed in a bond

paper

Instruction: Use one sheet of paper to answer the following questions. Each
number has corresponding point scores.

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 1. Name the following esters by the IUPAC System: 5 pts
A. HCO-OCH2CH2CH3
B. C6H5CO-OCH2CH3
C. CH3CH2OOC-CH2-COOCH2CH3
D. CH3CH2CO-OCH3
E. CH3CH2CH(CH3)CO-OCH2CH2CH3
2. Write structural formulas for: (4 pts)
A. Methyl formate
B. Butyl butanoate
3. Write the structural formula of the ester that when hydrolyzed would yield (4
pts)
A. Methanol and acetic acid
B. Ethanol and acetic acid
4. Write structural formulas for the reactants that will yield the following esters (4
pts)
A. Methyl palmitate
B. Phenyl propionate
5. Write equations showing: (8 pts)
A. the acid hydrolysis, and
B. the alkaline hydrolysis of isobutyl pentanoate

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