Organic Chemistry

CHAPTERS - 12 & 13

Introduction to Organic Chemistry:

Organic chemistry is the branch of chemistry that deals with the study of compounds
containing carbon atoms, typically bonded to hydrogen, oxygen, nitrogen, and other
elements.

Carbon is unique in its ability to form long chains and complex structures, making it the
foundation of organic compounds.

Organic compounds can be found in living organisms (biomolecules) and in synthetic

materials like plastics and pharmaceuticals.

Hydrocarbons:

Hydrocarbons are organic compounds made up of only carbon and hydrogen atoms.

Alkanes are saturated hydrocarbons with single bonds between carbon atoms.

Alkenes have at least one carbon-carbon double bond, and alkynes have at least one carbon-
carbon triple bond.

Aromatic compounds, like benzene, contain a special ring structure and alternating single and
double bonds.

Functional Groups:

Functional groups are specific atoms or groups of atoms within organic molecules that
determine the chemical properties of the compound.

Examples of common functional groups include alcohols (-OH), ketones (C=O), aldehydes
(C=O at the end of a carbon chain), and carboxylic acids (COOH).

Isomerism:

Isomers are compounds with the same molecular formula but different structural
arrangements or connectivity of atoms.

Structural isomers have different arrangements of atoms.

Stereoisomers have the same connectivity of atoms but differ in the spatial arrangement (cis-
trans isomerism and optical isomerism).
Reactivity in Organic Chemistry:

The reactivity of organic compounds is determined by factors like bond polarity, bond
strength, and the stability of intermediates.

Electrophiles are electron-deficient species that seek electrons (e.g., positive ions), while
nucleophiles are electron-rich species that donate electrons (e.g., negative ions).

Reaction mechanisms describe the step-by-step processes by which organic reactions occur,
such as substitution, addition, elimination, and rearrangement reactions.

Organic Synthesis:

Organic synthesis involves designing and executing chemical reactions to create organic
compounds from simpler starting materials.

Retrosynthetic analysis is a strategy used to work backward from a target molecule to

identify potential precursor molecules.

Nomenclature:

IUPAC (International Union of Pure and Applied Chemistry) rules are used to name organic
compounds systematically.

Common names are also used for many organic compounds, especially those with historical
significance.

Alkanes:

Alkanes are a type of hydrocarbon with the general formula CnH2n+2, where n is the number
of carbon atoms in the molecule.

Alkanes are also known as "saturated hydrocarbons" because they contain only single
covalent bonds between carbon atoms, making them saturated with hydrogen atoms.

The simplest alkane is methane (CH4), followed by ethane (C2H6), propane (C3H8), butane
(C4H10), and so on.

Alkanes are relatively unreactive due to the presence of strong carbon-carbon single bonds
and are often used as fuels.

Nomenclature of Alkanes:

IUPAC rules are used for systematic nomenclature of alkanes.

The parent chain is the longest continuous chain of carbon atoms in the molecule. The suffix
"-ane" is added to the root name of the alkane (e.g., ethane, propane).
Branches or substituents are named as alkyl groups and are prefixed with their position on
the parent chain (e.g., methyl, ethyl, propyl).

The numbering of carbon atoms in the parent chain starts at the end nearest to a substituent,
and the substituents are assigned numbers accordingly.

Isomerism in Alkanes:

Alkanes exhibit structural isomerism, where different isomers have the same molecular
formula but different structural arrangements.

Chain isomerism involves changing the arrangement of the carbon skeleton (e.g., branching).

Position isomerism involves changing the position of the substituent on the parent chain.

Physical Properties of Alkanes:

Alkanes are generally gases or liquids at room temperature and pressure, with increasing
boiling points as the molecular weight increases.

They are nonpolar molecules, resulting in weak London dispersion forces between molecules.

Alkanes are relatively insoluble in water but are soluble in nonpolar solvents.

Chemical Reactions of Alkanes:

Alkanes undergo very limited reactivity due to the strong and nonpolar nature of carbon-
carbon single bonds.

They can combust in the presence of oxygen to produce carbon dioxide and water, releasing
energy (e.g., in engines and heaters).

Alkanes can be halogenated (chlorinated or brominated) under specific conditions, but these
reactions typically require the presence of ultraviolet (UV) light or heat to initiate.

Alkanes do not readily undergo addition reactions or reactions with common acids and bases.

Alkenes:

Alkenes are a type of hydrocarbon with the general formula CnH2n, where n is the number of
carbon atoms in the molecule.

Alkenes are also known as "olefins" and are characterized by the presence of at least one
carbon-carbon double bond (C=C).

The simplest alkene is ethene (C2H4), followed by propene (C3H6), butene (C4H8), and so on.

The presence of the carbon-carbon double bond introduces a degree of unsaturation, making
alkenes more reactive than alkanes.
Nomenclature of Alkenes:

IUPAC rules are used for systematic nomenclature of alkenes.

The parent chain is the longest continuous chain of carbon atoms in the molecule containing
the double bond. The suffix "-ene" is added to the root name of the alkene (e.g., ethene,
propene).

The location of the double bond is indicated by the lowest number of the carbon atoms
involved in the double bond.

Geometric Isomerism (Cis-Trans Isomerism):

Alkenes with two different substituents on each carbon of the double bond can exhibit
geometric isomerism.

Cis-isomers have similar groups on the same side of the double bond, while trans-isomers
have similar groups on opposite sides of the double bond.

The geometric isomerism arises due to the restricted rotation around the carbon-carbon
double bond.

Physical Properties of Alkenes:

Alkenes are generally gases or liquids at room temperature and pressure, with increasing
boiling points as the molecular weight increases.

They are slightly more reactive than alkanes due to the presence of the double bond, which
can undergo addition reactions.

Chemical Reactions of Alkenes:

Alkenes readily undergo addition reactions, where atoms or groups of atoms are added to the
carbon-carbon double bond.

Common addition reactions include hydrogenation (addition of hydrogen), halogenation

(addition of halogens), hydration (addition of water), and hydrohalogenation (addition of
hydrogen halides).

Alkenes can also undergo polymerization reactions, where monomers with double bonds
combine to form long chains in processes like the production of plastics.

They are more susceptible to electrophilic attack compared to alkanes due to the presence of
the electron-rich double bond.

Alkenes can also participate in reactions involving radical intermediates, such as radical
polymerization.
Uses of Alkenes:

Alkenes are important raw materials in the chemical industry and are used to synthesize a
wide range of organic compounds, including plastics, solvents, and pharmaceuticals.

Ethene (ethylene) is used in the production of polyethylene, one of the most widely used
plastics in the world.

What Are Polymers?

Polymers are large molecules made up of repeating structural units called monomers.

The process of joining monomers to form a polymer is called polymerization.

Polymers can have varying sizes, from very large macromolecules to smaller ones, depending
on the number of repeating units.

Types of Polymers:

Natural Polymers: These are found in nature and include substances like proteins, cellulose,
and DNA.

Synthetic Polymers: These are man-made polymers, including plastics like polyethylene and
polypropylene.

Semi-synthetic Polymers: These are derived from natural polymers but are chemically
modified. Examples include cellulose acetate and rayon.

Classification Based on Polymerization Mechanism:

Addition (Chain-Growth) Polymers: These polymers are formed through the repeated
addition of monomers with unsaturated double bonds (e.g., polyethylene, PVC).

Condensation (Step-Growth) Polymers: These polymers are formed through the elimination
of small molecules (e.g., water or methanol) as monomers react (e.g., polyester, nylon).

Properties of Polymers:

Molecular Weight: Polymers can have a wide range of molecular weights, affecting properties
like viscosity, mechanical strength, and melting point.

Amorphous vs. Crystalline: Polymers can exist in amorphous (random) or crystalline

(ordered) structures, influencing properties like transparency, stiffness, and melting behavior.

Thermal Stability: Polymers have varying thermal stability, with some melting or
decomposing at high temperatures, while others have high heat resistance.

Solubility: Polymers can be soluble or insoluble in various solvents, depending on their

chemical structure and polarity.
Applications of Polymers:

Plastics: Used in countless applications, including packaging, automotive components, toys,

and medical devices.

Rubbers: Used for tires, seals, gaskets, and various elastomeric products.

Fibers: Used in textiles and clothing, such as polyester, nylon, and acrylic fibers.

Adhesives: Polymers are used in various adhesives and sealants.

Biopolymers: Natural polymers like DNA and proteins are crucial for biological processes.

Environmental Impact:

The disposal of synthetic polymers, especially single-use plastics, has led to environmental
concerns due to their persistence in the environment.

Efforts are being made to develop biodegradable polymers and promote recycling to reduce
the environmental impact.

Polymer Processing:

Polymers can be processed into various forms, including extrusion, injection molding, blow
molding, and casting.

The choice of processing method affects the properties and applications of the polymer
product.

What Are Alcohols?

Alcohols are a class of organic compounds characterized by the presence of one or more
hydroxyl (-OH) functional groups attached to carbon atoms.

The general formula for alcohols is R-OH, where R represents an alkyl group (a hydrocarbon
chain).

Classification of Alcohols:

Primary Alcohols: In primary alcohols, the carbon atom to which the hydroxyl group is
attached is bonded to only one other carbon atom. Examples include ethanol (CH3CH2OH)
and methanol (CH3OH).

Secondary Alcohols: In secondary alcohols, the carbon atom with the hydroxyl group is
bonded to two other carbon atoms. An example is isopropanol (CH3CHOHCH3).

Tertiary Alcohols: Tertiary alcohols have the hydroxyl group attached to a carbon atom
bonded to three other carbon atoms. An example is tert-butyl alcohol [(CH3)3COH].
Physical Properties of Alcohols:

Alcohols with a small number of carbon atoms are typically liquids at room temperature,
while those with larger carbon chains can be solids or liquids.

They can form hydrogen bonds due to the presence of the hydroxyl group, leading to higher
boiling points compared to hydrocarbons of similar size.

Alcohols are often polar compounds, making them soluble in water to varying degrees,
depending on the size of the hydrocarbon chain.

Chemical Reactions of Alcohols:

Oxidation: Primary alcohols can be oxidized to form aldehydes and then further oxidized to
carboxylic acids. Secondary alcohols can be oxidized to ketones. Tertiary alcohols do not
undergo oxidation under normal conditions.

Dehydration: Alcohols can undergo dehydration reactions, where water is eliminated,

resulting in the formation of alkenes. Acid-catalyzed dehydration is a common method.

Substitution Reactions: Alcohols can undergo substitution reactions to replace the hydroxyl
group with other functional groups. For example, the hydroxyl group can be replaced with a
halogen atom (e.g., via the Appel reaction).

Esterification: Alcohols can react with carboxylic acids to form esters and water in the
presence of an acid catalyst.

Uses of Alcohols:

Ethanol (Ethyl Alcohol): Used as a beverage, solvent, and fuel additive. It is also used in the
pharmaceutical and cosmetic industries.

Methanol (Methyl Alcohol): Used as an industrial solvent and antifreeze. It is also a precursor
for the production of formaldehyde and various chemicals.

Isopropanol (Isopropyl Alcohol): Used as a disinfectant, antiseptic, and solvent. It is

commonly found in rubbing alcohol.

Tert-Butyl Alcohol: Used as a solvent and as a raw material in the synthesis of other
chemicals.

Cetyl Alcohol and Stearyl Alcohol: Used in cosmetics and personal care products as
emollients and thickeners.

What Are Carboxylic Acids?

Carboxylic acids are a class of organic compounds characterized by the presence of a

carboxyl functional group, which consists of a carbonyl group (C=O) and a hydroxyl group (-
OH) attached to the same carbon atom.
The general formula for carboxylic acids is RCOOH, where R represents an alkyl group or a
hydrogen atom.

Nomenclature of Carboxylic Acids:

The IUPAC naming of carboxylic acids typically involves replacing the -e ending of the
corresponding alkane with -oic acid. For example, methane becomes methanoic acid.

Common names for some carboxylic acids are also widely used, such as formic acid
(methanoic acid), acetic acid (ethanoic acid), and citric acid.

Physical Properties of Carboxylic Acids:

Carboxylic acids are polar compounds due to the presence of the carbonyl group and the
hydroxyl group, allowing them to form hydrogen bonds.

They are typically colorless liquids or solids at room temperature, with strong and often
pungent odors.

Carboxylic acids are soluble in water due to hydrogen bonding; however, solubility decreases
as the carbon chain lengthens.

Chemical Reactions of Carboxylic Acids:

Acid-Base Reactions: Carboxylic acids can donate a proton (H+) to act as acids. They react
with bases to form carboxylate ions and water.

Esterification: Carboxylic acids can react with alcohols in the presence of an acid catalyst to
form esters and water. This reaction is commonly used in the synthesis of fragrances and
flavor compounds.

Decarboxylation: Under certain conditions, carboxylic acids can undergo decarboxylation,

resulting in the loss of a carbon dioxide molecule and the formation of a hydrocarbon. This is
often seen in the biosynthesis of fatty acids and in some organic reactions.

Reduction: Carboxylic acids can be reduced to primary alcohols using reducing agents such
as LiAlH4 or NaBH4.

Salt Formation: Carboxylic acids react with bases to form salts called carboxylates. For
example, acetic acid (CH3COOH) reacts with sodium hydroxide (NaOH) to form sodium
acetate (CH3COONa).

Uses of Carboxylic Acids:

Acetic Acid: Used in the production of vinegar, food preservation, and the manufacture of
synthetic fibers and plastics.
Citric Acid: Widely used as a food additive, acidulant, and flavoring agent. It's found in citrus
fruits and is essential in the food and beverage industry.

Formic Acid: Used in leather tanning, textile dyeing, and as a preservative in livestock feed.

Stearic Acid: Used in the production of soaps, cosmetics, and candles, as well as as a
lubricant and release agent in various industries.

Salicylic Acid: Used in the production of aspirin (acetylsalicylic acid) and in skincare products
for its keratolytic and anti-inflammatory properties.

What Are Esters?

Esters are a class of organic compounds characterized by the presence of the ester
functional group, which consists of a carbonyl group (C=O) bonded to an oxygen atom (O) and
another oxygen atom (O) bonded to a carbon atom (C) in an alkyl or aryl group.

The general formula for esters is RCOOR', where R and R' represent alkyl or aryl groups.

Nomenclature of Esters:

The IUPAC naming of esters typically involves naming the alkyl or aryl group bonded to the
oxygen atom followed by the name of the carboxylic acid from which it is derived, with the
ending -ate. For example, ethyl ethanoate is derived from acetic acid.

Common names are also widely used for many esters and often include the names of the
alkyl or aryl groups followed by the word "ester." For example, ethyl acetate is a common
name for ethyl ethanoate.

Formation of Esters:

Esters are often formed through a reaction between a carboxylic acid and an alcohol in the
presence of an acid catalyst. This reaction is called esterification.

The esterification reaction involves the removal of a water molecule (dehydration) from the
carboxylic acid and alcohol, resulting in the formation of the ester.

Physical Properties of Esters:

Esters are typically colorless, sweet-smelling compounds that contribute to the fragrances
and flavors of many fruits and flowers.

They have lower boiling points than carboxylic acids and can have pleasant, fruity odors.

Many esters are volatile and are used as flavorings and fragrances in the food and perfume
industries.

Chemical Reactions of Esters:

Hydrolysis: Esters can be hydrolyzed, meaning they react with water in the presence of an
acid or a base to produce a carboxylic acid (or its salt) and an alcohol.

Saponification: In basic hydrolysis, esters undergo saponification to produce a carboxylate

salt and an alcohol. This reaction is used in soap-making.

Transesterification: Esters can undergo transesterification, where the ester group is

transferred from one alcohol to another in the presence of a catalyst. This reaction is
important in the production of biodiesel.

Uses of Esters:

Flavorings and Fragrances: Many esters have pleasant odors and are used to add aroma and
flavor to food, beverages, and perfumes.

Solvents: Some esters are used as solvents in various industrial applications.

Plastics and Polymers: Esters are used as monomers in the production of some synthetic
polymers, such as polyesters.

Pharmaceuticals: Esters are found in various pharmaceuticals and prodrugs, where they play
a role in drug delivery and formulation.

What Are Condensation Polymers?

Condensation polymers are a class of polymers formed through condensation reactions, also
known as step-growth polymerization.

In condensation polymerization, small molecules, often water or another simple compound,

are eliminated as byproducts during the polymerization process.

Polymerization Process:

Condensation polymers are formed by the repeated condensation reactions between two or
more bifunctional monomers, which have two reactive functional groups.

The reactive functional groups in the monomers can be different, such as a carboxylic acid
group and an alcohol group, or they can be the same, as in the case of amino acids in protein
synthesis.

In each condensation step, a small molecule, typically water (H2O), is eliminated as a

byproduct.

The monomers link together through covalent bonds, creating a polymer chain.

Examples of Condensation Polymers:

Polyesters: Polyesters are a common type of condensation polymer formed from a

dicarboxylic acid and a diol (two alcohol groups). For example, polyethylene terephthalate
(PET) is a polyester used in plastic bottles.

Polyamides: Polyamides are condensation polymers formed from monomers containing

amine and carboxylic acid functional groups. Nylon is a well-known polyamide.

Proteins: Proteins are biological condensation polymers made up of amino acids. The
condensation reaction occurs between the amino group of one amino acid and the carboxyl
group of another, forming a peptide bond.

Polysaccharides: Polysaccharides, such as cellulose and starch, are condensation polymers

formed from sugar molecules (monosaccharides) through glycosidic linkages.

Properties of Condensation Polymers:

Condensation polymers can be thermoplastic or thermosetting, depending on their structure

and properties.

They tend to have higher melting points compared to addition (chain-growth) polymers.

Condensation polymers often have good chemical resistance and mechanical strength.

Applications of Condensation Polymers:

Polyesters are used in textiles (e.g., polyester fabric), packaging materials (e.g., PET bottles),
and films.

Polyamides like nylon are used in textiles, ropes, automotive parts, and engineering plastics.

Proteins serve as the building blocks of living organisms and are essential for various
biological functions.

Polysaccharides have many applications, including as food additives, thickeners, and in

pharmaceuticals.

Hydrolysis of Condensation Polymers:

Condensation polymers can undergo hydrolysis, a reverse condensation reaction, where the
polymer is broken down into its constituent monomers.

Hydrolysis can be used for recycling certain condensation polymers, but it can also lead to
the degradation of materials over time.

Types of Natural Polyamides:

Proteins: Proteins are one of the most well-known and abundant natural polyamides. They
are made up of amino acid monomers linked together through peptide bonds. Proteins have a
wide range of functions, including serving as enzymes, structural components (e.g., collagen),
and transport molecules (e.g., hemoglobin).
Nucleic Acids: Nucleic acids, such as DNA (deoxyribonucleic acid) and RNA (ribonucleic acid),
are also natural polyamides. They consist of nucleotide monomers linked together through
phosphodiester bonds. DNA carries genetic information, while RNA plays a role in protein
synthesis.

Structure and Properties:

Amino Acid Sequence: The specific sequence of amino acids in a protein determines its
structure and function. Amino acids are linked together in a linear chain, and the sequence is
encoded by the genetic information.

Secondary Structure: Proteins can form secondary structures such as alpha helices and beta
sheets, which are stabilized by hydrogen bonds between amino acids in the chain.

Tertiary Structure: The three-dimensional folding of a protein is known as its tertiary

structure. This folding is essential for the protein's function.

Quaternary Structure: Some proteins are composed of multiple polypeptide chains, and their
overall structure is called quaternary structure. Hemoglobin is an example of a protein with
quaternary structure.

Function: The function of a protein is determined by its structure. For example, enzymes have
active sites that bind to specific substrates, allowing them to catalyze chemical reactions.

Roles and Functions:

Enzymes: Proteins act as biological catalysts (enzymes) that facilitate chemical reactions in
living organisms.

Structural Proteins: Proteins like collagen and keratin provide structural support to tissues
and organs.

Transport Proteins: Hemoglobin transports oxygen in the bloodstream, while transport

proteins in cell membranes facilitate the movement of ions and molecules.

Immune Response: Antibodies, which are proteins, play a critical role in the immune system
by recognizing and neutralizing pathogens.

Gene Expression: RNA molecules are involved in gene expression and protein synthesis.

Biodegradability:

Many natural polyamides, such as proteins and nucleic acids, are biodegradable. They can be
broken down by enzymes and microorganisms in the environment.

Biodegradability is an important property for sustainable materials and waste management.

Applications:
Biomedical and pharmaceutical applications, including drug development and tissue
engineering, often involve natural polyamides.

Genetic research relies on the study of nucleic acids like DNA and RNA.

Food and nutrition sciences study proteins for their nutritional value and functional
properties.

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