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Organic chemistry is the study of carbon-containing compounds, their structure, properties, and reactions, which gained prominence after Friedrich Wöhler synthesized urea from inorganic materials in 1828. Carbon's unique bonding capabilities allow for a vast array of organic compounds, with various types of bonds including ionic and covalent, and hybridization affecting molecular geometry. Molecular properties such as dipole moments and intermolecular forces influence reactivity and solubility, with factors like inductive effects and steric hindrance playing significant roles in chemical behavior.

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4 views5 pages

Chapter One Editing

Organic chemistry is the study of carbon-containing compounds, their structure, properties, and reactions, which gained prominence after Friedrich Wöhler synthesized urea from inorganic materials in 1828. Carbon's unique bonding capabilities allow for a vast array of organic compounds, with various types of bonds including ionic and covalent, and hybridization affecting molecular geometry. Molecular properties such as dipole moments and intermolecular forces influence reactivity and solubility, with factors like inductive effects and steric hindrance playing significant roles in chemical behavior.

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Abraham Asefa
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What is Organic Chemistry?

❖ Historically, organic compounds were believed to contain a vital force derived from
living organisms, while inorganic compounds came from minerals. Jöns Jakob
Berzelius gave these names in 1807.
❖ Friedrich Wöhler challenged this in 1828 by producing urea, a compound from
mammals, by heating inorganic ammonium cyanate in the laboratory.

Friedrich Wöhler (1800–1882) was a German chemist


best known for synthesizing urea from ammonium cyanate
in 1828, a landmark discovery that helped disprove the
idea that organic compounds could only be made by living
organisms. This experiment is considered the beginning of
modern organic chemistry. Wöhler also made significant
contributions to inorganic chemistry, including work with
aluminum and beryllium.

❖ Organic chemistry is the study of the structure, properties, composition,


reactions, and preparation of carbon-containing compounds.
❖ Most organic compounds contain carbon and hydrogen, but they can also include
elements like nitrogen, oxygen, halogens, phosphorus, silicon, and sulfur.
❖ Carbonates and oxides are considered inorganic.
❖ There are millions of known organic compounds, far more than inorganic
compounds.

Why Carbon is Unique

❖ The uniqueness of carbon's structure and bonding capabilities is the reason for the
vast number of organic compounds.
❖ Carbon has four valence electrons, allowing it to make four separate covalent
bonds.
❖ Carbon can bond to itself repeatedly, forming long chains and ring structures.
❖ These carbon-carbon bonds can be single, double, or triple covalent bonds.

Atomic Orbitals and Bonding

❖ The behavior of an electron in an atom can be described by a wave function (ψ),


called an atomic orbital (AO).
❖ Atomic orbitals describe electron densities and are regions in space where an
electron is likely to be found. These regions have shape, size, and energy.
❖ Common elements in organic compounds (C, H, N, O) utilize 1s, 2s, and 2p atomic
orbitals.

Why Atoms Form Bonds

❖ Bond formation primarily occurs for each atom to achieve an inert gas electron
configuration in its valence level. This is often a valence octet (eight electrons),
except for hydrogen which needs two to match helium's configuration.
❖ Atoms can achieve this stable configuration by giving up electrons, accepting
electrons, or sharing electrons.
❖ Noble gases are inert because they have a stable electronic configuration, usually
with eight electrons in the outer shell (except helium), and thus don't typically donate
or gain electrons.
❖ Electrons in filled shells are called core electrons and do not participate in bonding.
❖ Electrons in shells that are not completely filled are called valence electrons and are
in the valence shell.
❖ Carbon, with configuration 1s² 2s² 2p², has four valence electrons. Lewis structures
represent these outermost electrons.

Types of Bonds

❖ The two major types are Ionic and Covalent bonds.


❖ Ionic bonds result from the transfer of one or more electrons. The more
electronegative atom gains electrons and becomes an anion, while the less
electronegative atom loses electrons and becomes a cation.
❖ Covalent bonds result from the sharing of electrons between atoms to achieve a
filled valence shell. A chemical bond is the attractive force holding two atoms
together.
❖ Covalent bonds result from the overlap of singly occupied atomic orbitals to form a
bonding molecular orbital (MO) where electrons interact with both nuclei. These
electrons are more tightly bound (lower energy) and are more likely to be found
between the nuclei.

Covalent Bond Overlap

❖ There are two types of orbital overlap: sigma (δ) and pi (Π) bonds.
❖ Pi bonds never occur alone; atoms joined by a pi bond must also have a sigma bond.
❖ A double bond consists of one δ bond and one Π bond.
❖ A triple bond consists of one δ bond and two Π bonds.
❖ Sigma (δ) overlap happens when bonding interaction results from the head-to-head
overlap of two s orbitals, an s orbital and a p orbital, or two p orbitals.
❖ Pi (Π) overlap happens when two bonding interactions result from the sideways
overlap of two parallel p orbitals.
❖ s orbitals are spherical, and p orbitals are dumb-bell shaped.

Hybrid Orbitals and Molecular Geometry

❖ Atoms can hybridize their atomic orbitals to form hybrid orbitals, which provide
greater electron density in the bonding region and keep electron pairs as far apart as
possible.
❖ sp hybrid orbitals: Have 2 VSEPR pairs, linear electron pair geometry, and a 180°
bond angle. Example: BeH₂ is linear with a 180° bond angle.
❖ sp² hybrid orbitals: Have 3 VSEPR pairs, trigonal planar geometry, and a 120° bond
angle. Hybridization of one s and two p orbitals gives three sp² orbitals directed 120°
apart. Example: Borane (BH₃) is planar and trigonal.
❖ sp³ hybrid orbitals: Have 4 VSEPR pairs, tetrahedral electron pair geometry, and a
109.5° bond angle. Example: Ammonia (NH₃) has three sigma bonds and one lone
pair around nitrogen, requiring four hybrid orbitals, implying sp³ hybridization and
tetrahedral geometry around N, with angles slightly less than 109.5° due to the lone
pair.
❖ Hybridization depends on the number of sigma bonds plus lone pairs.

Bonding Examples

❖ Ethane: Composed of two methyl groups bonded by the overlap of their sp³ hybrid
orbitals (forming a sigma bond). There is free rotation along this single bond.
❖ Ethylene: Has three sigma bonds formed by sp² hybrid orbitals in a trigonal planar
geometry. The unhybridized p orbital on each carbon is perpendicular to the sp²
orbitals and parallel to the other carbon's unhybridized p orbital. Overlap of these two
p orbitals forms a pi bond located above and below the sigma bond. Double bonds
cannot rotate.
Molecular Properties Influenced by Bonding

❖ Bond Dipole Moments: Due to differences in electronegativity. Shared electron pairs


are not necessarily shared equally, leading to bond polarity. More electronegative
atoms (N, O, halogens) tend to have partial negative charges when bonded to carbon.
Dipole moments depend on charge amount and separation distance and are
measured in debyes (D).
❖ Molecular Dipole Moments: The vector sum of bond dipole moments. They depend
on bond polarity and bond angles. Lone pairs of electrons also contribute.
❖ Intermolecular Forces (IMFs): Attractions between molecules that influence
melting point (m. p.), boiling point (b. p.), and solubility.
➢ Dipole–Dipole Interactions: Result from the approach of two polar
molecules. Attractive when positive and negative ends are near, repulsive
otherwise. In liquids/solids, molecules are mostly oriented for attraction, so
the net force is attractive.
➢ London Dispersions: One type of Van der Waals force. A temporary dipole in
one molecule can induce a temporary dipole in a nearby molecule, leading to
a short-lived attractive dipole-dipole interaction. This is the main force in
nonpolar molecules. Larger atoms are more polarizable. Branching lowers the
boiling point due to decreased surface contact.
➢ Hydrogen Bonding: A strong dipole-dipole attraction. Organic molecules
need an N—H or O—H group to hydrogen bond. The hydrogen from one
molecule is strongly attracted to a lone pair on oxygen or nitrogen of another
molecule. The O—H bond is more polar than the N—H bond, so alcohols have
stronger hydrogen bonding than amines. Hydrogen bonding increases the
boiling point of a molecule. Examples show ethanol (OH, b.p. 78°C) has a
much higher b.p. than dimethyl ether (no OH, b.p. -25°C) or ethyl amine (NH₂,
b.p. 17°C).
❖ Solubility: Often described by "like dissolves like". Polar solutes dissolve in polar
solvents, and nonpolar solutes dissolve in nonpolar solvents. Molecules with similar
intermolecular forces will mix freely. A polar solute dissolves in a polar solvent
because hydration releases energy and entropy increases. A polar solute won't
dissolve in a nonpolar solvent because the solvent cannot break the solute's
intermolecular interactions. A nonpolar solute dissolves in a nonpolar solvent
because the weak attractions of the solute are overcome by the weak attractions for
the solvent. Nonpolar substances generally do not dissolve in water because
dissolving them would break the hydrogen bonds between water molecules.

Factors Influencing Reactivity

❖ Inductive Effects: Electronic effects transmitted through bonds. They can be


electron donating or electron withdrawing. They weaken as the distance from the
group increases. These are related to electronegativity and bond polarity.
❖ Delocalization/Resonance: Delocalization of charge (e.g., in a carboxylate anion) is
possible through resonance structures, which stabilizes the charge by distributing it
over multiple atoms. This delocalization effect is not possible in an alkoxide ion.
❖ Steric Effect/Steric Hindrance: Effects on reaction rates caused by the spatial
arrangement (space-filling properties) of atoms or groups near the reacting site.
Steric hindrance occurs when this arrangement hinders or retards a reaction.

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