ORGANIC CHEMISTRY

Lesson 1/ Finals
CARBOXYLIC ACIDS
• a class of organic compounds containing the
carbonyl group.
• The functional group of a carboxylic acid is a
carboxyl group, which can be represented in any
one of three ways.

IUPAC names
• For an acyclic carboxylic acid, take longest carbon
chain that contains the carboxyl group as the parent
alkane.
• Drop the final -e from the name of the parent alkane • For common names, use, the Greek letters alpha (a),
and replace it by -oic acid. beta (b), gamma (g), and so forth to locate
• Number the chain beginning with the carbon of the substituents.
carboxyl group.
• Because the carboxyl carbon is understood to be
carbon 1, there is no need to give it a number.
Nomenclature
• In these examples, the common name is given in Physical Properties
parentheses. • The carboxyl group contains three polar covalent
bonds; C=O, C-O, and O-H.
o The polarity of these bonds determines the
major physical properties of carboxylic acids.
• An -OH substituent is indicated by the prefix
hydroxy-; an -NH2 substituent by the prefix amino.

• To name a dicarboxylic acid, add the suffix -dioic

acid to the name of the parent alkane that contains
both carboxyl groups; thus, -ane becomes -anedioic
acid.
• The numbers of the carboxyl carbons are not
indicated because they can be only at the ends of the
chain.
• Carboxylic acids have significantly higher boiling
points than other types of organic compounds of
comparable molecular weight.
• Their higher boiling points are a result of their
polarity and the fact that hydrogen bonding between
two carboxyl groups creates a dimer that behaves as
a higher-molecular-weight compound.
o Polarity – donation of electrons or chemical
charge over the atoms joined by the bond. It
can also be identify by the electronegativity
of the atom.
o Branching decreases boiling point – the
more branch, the less boiling point. Linear and
branch molecules have higher boiling point
than with more branches.

• Carboxylic acids are more soluble in water than are

alcohols, ethers, aldehydes, and ketones of
comparable molecular weight.
• Mas maraming carbon, mas mataas ang boiling
point.
1
 ORGANIC CHEMISTRY
Lesson 1/ Finals
• https://davidson.weizmann.ac.il/en/online/askexpert/
chemistry/what-difference-between-saturated-and-
unsaturated-fat-and-what-are-trans-fats-eyal

• Butanoic Acid is stronger IMF than alcohol and it

has a double bond of carbon and OH. • Unsaturated fatty acids generally have lower melting
Vapor pressure points than their saturated counterparts.
• Vapor pressure is a measure of the tendency of a o Not enough hydrogen atom
material to change into the gaseous or vapor state,
and it increases with temperature. The temperature at
which the vapor pressure at the surface of a liquid
becomes equal to the pressure exerted by the
surrounding is called the boiling point of the liquid.
• When liquid is heated, its molecules obtain sufficient
kinetic energy to overcome the forces holding them
in the liquid and they escape into the gaseous phase. • Saturated fatty acids are solids at room temperature;
By doing so, they generate a population of the regular nature of their hydrocarbon chains allows
molecules in the vapor phase above the liquid that them to pack together in such a way as to maximize
produces a pressure – the vapor pressure of the interactions (by London dispersion forces) between
liquid. their chains.
Fatty Acids o Solid texture/compound or molecule.
• Long chain carboxylic acids derived from animal
fats, vegetable oils, or phospholipids of biological
membranes.
o Vegetable oil is mostly polyunsaturated fats
while animal fat is composed mostly of
• In contrast, all unsaturated fatty acids are liquids at
monounsaturated fats. It is full of hydrogen
room temperature because the cis double bonds
bonds. Vegetable fats contain one, or more,
interrupt the regular packing of their hydrocarbon
carbon double bonds within its structure and are
chains.
therefore unsaturated. Animal fats contain only
single carbon-carbon bonds and are therefore
saturated.
• More than 500 have been isolated from various cells
and tissues.
• Most have between 12 and 20 carbons in an
unbranched chain.
• In most unsaturated fatty acids, the cis isomer
predominates; trans isomers are rare.
• Unsaturated fatty acids have lower melting points
than their saturated counterparts.
o The intermolecular interactions are much weaker
than saturated molecules. In that case, the melting
point is much lower for unsaturated fatty acids.

2
 ORGANIC CHEMISTRY
Lesson 1/ Finals

Cis- and Trans- fatty acids

 Omega-3 fatty acids are polyunsaturated fats, a type
of fat your body can’t make.
 The term “polyunsaturated” refers to their chemical
structure, as “poly” means many and “unsaturated”
refers to double bonds. Together they mean that
omega-3 fatty acids have many double bonds.
 “Omega-3” refers to the position of the final double
bond in the chemical structure, which is three carbon
atoms from the “omega,” or tail end of the molecular
chain.
 Since the human body can’t produce omega-3s,
these fats are referred to as “essential fats,” meaning
that you have to get them from your diet.
• Location of the hydrogen of the double bond
 Omega-3 fats are essential fats that you must get
Trans fats and the body
from your diet. They have important benefits for
They have more ability to stick together in the walls of
your heart, brain, and metabolism.
the blood vessel.
 Like omega-3s, omega-6 fatty acids are
polyunsaturated fatty acids. However, the last double
bond is six carbons from the omega end of the fatty
acid molecule.
 Omega-6 fatty acids are also essential, so you need
to obtain them from your diet.
 They mainly provide energy. The most common
omega-6 fat is linoleic acid, which the body can
convert to longer omega-6 fats such as arachidonic
acid (AA)
 Pro-inflammatory eicosanoids play a key role in the
immune system. However, when the body produces
too many, they can increase the risk of inflammation Soaps
and inflammatory disease. • Natural soaps are sodium or potassium salts of fatty
 Omega-6 fats are essential fats that provide energy acids.
for the body. However, people should eat more • They are prepared from a blend of tallow and palm
omega-3s than omega-6s. oils (triglycerides).
• Triglycerides are triesters of glycerol.
• the solid fats are melted with steam and the water
insoluble triglyceride layer that forms on the top is
removed.
• Preparation of soaps begins by boiling the
triglycerides with NaOH. The reaction that takes

3
 ORGANIC CHEMISTRY
Lesson 1/ Finals
place is called saponification (Latin: saponem,
“soap”). Boiling with KOH gives a potassium soap.
o Potassium Hydroxide, Sodium
Hydroxide and Lye
o Both Potassium and Sodium Hydroxide
are neutral, that is why they are not
harmful.
• In water, soap molecules spontaneously cluster into
micelles, a spherical arrangement of molecules such
that their hydrophobic parts are shielded from the
aqueous environment, and their hydrophilic parts
are in contact with the aqueous environment.
• When soap is mixed with dirt (grease, oil, and fat
stains), soap micelles “dissolve” these nonpolar,
water-insoluble molecules.
o Even if the soup does not have anti-bacterial
property, because the soup can break the protein
compound of the cell membrane of the
pathogens, even the viruses.
o Even the oil or the fatty acids of the cell
membrane.
• Natural soaps form water-insoluble salts in hard
water.
• Hard water contains Ca (II), Mg (II) and Fe (III)
ions.
o They have ions or metallic ions.
Detergents
• The problem of formation of precipitates in hard
water was overcome by using a molecule containing
a -SO3- group (sulfonic acid group) in the place of a
-CO2- group.
4
o Calcium, magnesium, and iron salts of sulfonic
acids, RSO3H, are more soluble in water than
salts of fatty acids.
o Following is the preparation of the synthetic
detergent, SDS, a linear alkylbenzene sulfonate
(LAS), an anionic detergent.
• Among the most common additives to detergents are
foam stabilizers, bleaches, and optical brighteners.
Acidity of RCOOH
• Carboxylic acids are weak acids:
o Values of Ka for most unsubstituted aliphatic
and aromatic carboxylic acids fall within the
range 10-4 to 10-5 (pKa 4.0 - 5.0). Slightly
acidic.
• Substituents of high electronegativity, especially
-OH, -Cl, and -NH3+, near the carboxyl group
increase the acidity of carboxylic acids.
• Both dichloroacetic acid and trichloroacetic acid are
stronger acids than H3PO4 (pKa 2.1).
• When a carboxylic acid is dissolved in aqueous
solution, the form of the carboxylic acid present
depends on the pH of the solution in which it is
dissolved.
Reaction with Bases
• All carboxylic acids, whether soluble or insoluble in
water, react with NaOH, KOH, and other strong
bases to form water-soluble salts.
• They also form water-soluble salts with ammonia
and amines.
 ORGANIC CHEMISTRY
Lesson 1/ Finals
• Like inorganic acids, carboxylic acids react with • An exception is any carboxylic acid that has a
sodium bicarbonate and sodium carbonate to form carbonyl group on the carbon b to the COOH group.
water-soluble sodium salts and carbonic acid. • Decarboxylation of a b-ketoacid.
• Carbonic acid then decomposes to give water and
carbon dioxide, which evolves as a gas.

Fischer Esterification • The mechanism of thermal decarboxylation involves

• Fischer esterification is one of the most commonly (1) redistribution of electrons in a cyclic transition
used preparations of esters. state, (2) followed by keto-enol tautomerism.
• In Fischer esterification, a carboxylic acid is reacted
with an alcohol in the presence of an acid catalyst,
most commonly concentrated sulfuric acid.
• An important example of decarboxylation of a b-
ketoacid in biochemistry occurs during the oxidation
o Fischer esterification is reversible. of foodstuffs in the tricarboxylic acid (TCA) cycle.
o It is possible to drive it in either direction by Oxalosuccinic acid, one of the intermediates in this
the choice of experimental conditions (Le cycle, has a carbonyl group (in this case a ketone) b
Chatelier’s principle). to one of its three carboxyl groups.
• In Fischer esterification, the alcohol adds to the
carbonyl group of the carboxylic acid to form a
tetrahedral carbonyl addition intermediate.
• The intermediate then loses H2O to give an ester.

Phosphoric Esters
• Phosphoric acid forms mono-, di-, and triphosphoric
esters.
• In more complex phosphoric esters, it is common to
name the organic molecule and then indicate the
presence of the phosphoric ester by either the word
"phosphate" or the prefix phospho-.
• Dihydroxyacetone phosphate and pyridoxal
phosphate are shown as they are ionized at pH 7.4,
the pH of blood plasma.

Decarboxylation
• Decarboxylation: the loss of CO2 from a carboxyl
group.

• Almost all carboxylic acids, when heated to a very

high temperature, will undergo thermal
decarboxylation.
• Most carboxylic acids, however, are resistant to
moderate heat and melt and even boil without
undergoing decarboxylation.