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Module 1A

Schools Requirements

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Module 1A

Schools Requirements

Uploaded by

Princess De Leon Rodriguez
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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Module 1A

Review Chapter: Structure and Bonding

-Do not distribute without permission-


Organic chemistry is study of carbon compounds. Ninety percent of more than 30 million
chemical compounds contain carbon. Carbon is group 4A element, it can share 4 valence
electrons and form 4 covalent bonds.

Figure 1: The periodic table of elements. Illustration from Brooks/Cole Cengage Learning.

Learning Objectives
This module will consider:
• what kinds of atoms that make up organic molecules.
• the principles that determine how the atoms in organic molecules are bound together.
• how to best depict organic molecules.

1 The Atom
1.1 Atomic Structure
• An atom has a small diameter - 2×10−10 m or 200 pm.
• It consists of a nucleus (with a diameter of ∼10−15 m), which is surrounded by a cloud
of electrons. The nucleus consists of a proton and a neutron.
– Proton - positively charged
– Electron - negatively charged
– Neutron - uncharged or neutral

GPMAYLEM 1 Organic Chemistry ∥ 2022


Figure 2: The volume around the nucleus (protons + neutrons) is occupied by orbiting electrons.
Illustration from Brooks/Cole Cengage Learning.

1.2 Atomic Number and Atomic Mass


• Atomic number (Z) - number of protons in nucleus

• Mass number (A): number of protons plus neutrons

• All atoms of same element have the same Z value.

• Isotopes - atoms of the same element with different numbers of neutrons and thus different
A (Figure 8)

• The atomic mass (atomic weight) of an element is weighted average mass in atomic mass
units (amu) of an element’s naturally occurring isotopes.

Figure 3: Isotopes of carbon. Illustration from Brooks/Cole Cengage Learning.

1.3 Atomic Orbitals


• Four different kinds of orbitals for electrons based on those derived for a hydrogen atom

• Denoted s, p, d, and f

• s and p orbitals most important in organic and biological chemistry

• s orbitals: spherical, nucleus at center

• p orbitals: dumbbell-shaped, nucleus at middle

• d orbitals: elongated dumbbell-shaped, nucleus at center

For the following items, refer to Figure 5.

• Orbitals are grouped in shells of increasing size and energy

• Different shells contain different numbers and kinds of orbitals

GPMAYLEM 2 Organic Chemistry ∥ 2022


Figure 4: Shapes of s, p, and d orbitals. Illustration from Brooks/Cole Cengage Learning.

• Each orbital can be occupied by two electrons

• First shell contains one s orbital, denoted 1s, holds only two electrons

• Second shell contains one s orbital (2s) and three p orbitals (2p), eight electrons

• Third shell contains an s orbital (3s), three p orbitals (3p), and five d orbitals (3d ), 18
electrons

Figure 5: Orbitals are grouped in shells of increasing size and energy. Illustration from
Brooks/Cole Cengage Learning.

2 Chemical Bonding Theory


• Atoms form bonds because the resulting compound is more stable than the separate
atoms.

• Ionic bonds in salts form by electron transfers.

• Organic compounds have covalent bonds from sharing electrons.

• Lewis structures (electron dot) show valence electrons of an atom as dots. For example,
hydrogen has one dot, representing its 1s electron, while carbon has four dots (2s2 2p2 )
due to 4 e- in valence shell.

• Kekulé structures (line-bond structures) have a line drawn between two atoms indi-
cating a 2 e- covalent bond.

GPMAYLEM 3 Organic Chemistry ∥ 2022


• Carbon has four valence electrons (2s2 2p2 ), forming four bonds (CH4 ).

• Nitrogen has five valence electrons (2s2 2p3 ) but forms only three bonds (NH3 ).

• Oxygen has six valence electrons (2s2 2p4 ) but forms two bonds (H2 O).

• Valence electrons not used in bonding are called nonbonding electrons, or lone-pair
electrons. Nitrogen atom in ammonia (NH3 ) shares six valence electrons in three covalent
bonds and remaining two valence electrons are nonbonding lone pair.

• Covalent bond forms when two atoms approach each other closely so that a singly
occupied orbital on one atom overlaps a singly occupied orbital on the other atom.

• Two models to describe covalent bonding: valence bond theory and molecular orbital
theory.

• Valence bond theory - electron sharing occurs by overlap of two atomic orbitals

• Molecular orbital (MO) theory - bonds result from combination of atomic orbitals
to give molecular orbitals, which belong to the entire molecule

• Sigma (σ) bonds - circular cross-section and are formed by head- on interaction

• Pi (π) bonds - “dumbbell” shape from sideways interaction of p orbitals

Figure 6: Lewis structures of methane (CH4 ), ammonia (NH3 ), water (H2 O), and methanol
(CH3 OH). Illustration from Brooks/Cole Cengage Learning.

Figure 7: Kekulé structures of methane (CH4 ), ammonia (NH3 ), water (H2 O), and methanol
(CH3 OH). Illustration from Brooks/Cole Cengage Learning.

GPMAYLEM 4 Organic Chemistry ∥ 2022


Figure 8: Number of bonds formed by H, C, N, and O. Illustration from Brooks/Cole Cengage
Learning.

References
1. McMurry, J. (1984). Organic chemistry. Monterey, CA: Brooks/Cole Pub. Co.

GPMAYLEM 5 Organic Chemistry ∥ 2022

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