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Class 1-Introduction

Introduction to organic chemistry

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Class 1-Introduction

Introduction to organic chemistry

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INTRODUCTION TO MATERIALS

ENGINEERING AND CHEMISTRY


MMCE8820B-1-R-2024F
Fall 2024
Instructor: Khalilalrahman Dehvari

Lectures: Monday 2:30-5:30, Location: 105 Memorial Hall


Office Hours: Tuesday 2:00-4:00 Essex Hall 253
periodic%20table

http://www.webelements.com/
Alkali Metals
▪ High reactivity, especially with water and air

▪ Found in combination with other elements in nature, NaCl, KCl, Na2CO3

▪ Reactivity increases down the group because the outer electron is further from the
nucleus and is more easily lost, resulting in a stronger reaction.

▪ When alkali metals react with water, they form a hydroxide and hydrogen gas.

2Cs(s)+2H2​O(l)→2CsOH(aq)+H2​(g)

▪ lithium has the highest reduction potential (-3.04V) and is the strongest reducing agent of all
elements.
Alkaline Earth Metals

Be, Mg
Transition Metals

Ca, Sr

Ba, Ra
• Carbon forms strong covalent bonds with other carbon atoms, leading to the
formation of long chains and complex structures.

• Carbon forms multiple bonds (double and triple bonds)

Alkanes (Saturated Hydrocarbons, CₙH₂ₙ₊₂)

Alkenes (Unsaturated Hydrocarbons with Double Bonds, CₙH₂ₙ)

Alkynes (Unsaturated Hydrocarbons with Triple Bonds, CₙH₂ₙ₋₂)


VB Description of Carbon-Carbon Single Bond (Ethane)

A σ-bond is defined by having rotational symmetry over the


internuclear axis (no phase change when rotated). 1s of H

rotation by 180 degree


gives a different
conformer of the same
molecule;

 bonds between
H and C are
σ-Bonds usually generated by
combining sp3 and s
allow for a free
orbitals
rotation over the
bond axis.
VB Model of Carbon-Carbon Double Bond (Ethene)
 bonds between
H and C

1s of H
-Bonds do not allow
for free rotation over
the bond axis.

A -bond by definition has no rotational symmetry over the internuclear axis


(phase inverts when rotated by 180º).
VB Model of Carbon-Carbon Triple Bond (Ethyne)
 bonds between
H and C

Hybrid orbitals form sigma bonds and unhybridized


ones make Pi bonds.
Every single bond contains one sigma bond
A triple bond is stronger than a single bond
Representation of Molecular structure
1. Chemical Formula-Based Representations
•Molecular Formula: Ethanol (C₂H₆O)
•Empirical Formula: C₂H₆O and CH₂O
•Condensed Formula: CH₃CH₂OH

2. Bonding and Electron-Based Representations


•Lewis Structures
•Structural Formula
•Resonance Structures

3. Spatial (3D) Representations


•Ball-and-Stick Model
•Space-Filling Model
•Wireframe Model
4. Hybrid Representations
•Line-Angle (Skeletal) Formula
•Wedge-Dash Notation
Representation of Molecular structure
Chemical Formula-Based Representations
5. Projection Representations
•Fischer Projection
•Newman Projection
•Haworth Projection
•Zigzag (Sawhorse) Projection

6. Computational and Analytical Representations


•Crystallographic Models:
•Molecular Graphs:
•Computational Models:

https://www.chm.bris.ac.uk/~paulmay/temp/pcc/displaying3d.htm
Representation of Molecular structure

•2D Representations: Lewis structures, full structural formulas, Fischer projections,


resonance structures

•3D Representations: Ball-and-stick models, space-filling models, crystallographic models,


molecular graphs

•Hybrid Representations: Line-angle formulas, tetrahedral stereochemistry notation

These are not explicit or universally accepted classifications.


Lewis dot structure
A Lewis dot structure of an atom represents only its valence electrons using dots placed around the element’s symbol.
Lewis dot structure
A Lewis dot structure is a diagram that represents the valence electrons of atoms within a molecule. These structures
show how atoms bond in a molecule and where lone pairs of electrons reside.

•Count the total valence electrons

•Determine the central atom

•Draw single bonds between atoms

•Complete the octets of outer atoms, then the central atom

Octet rule says that atoms like to have full outer shells of only eight electrons.
Atoms will lose or gain valence electrons to make their outer shells full, and they do this by bonding with other
atoms.
Lewis dot structure
Water H2O 8
•Count the total valence electrons:
•Add up the number of valence electrons for all atoms in the molecule. Add electrons for negative charges or
subtract for positive charges for polyatomic ions.

•Determine the central atom:


•Usually, the least electronegative atom (except hydrogen) is placed in the
HOH
center. Hydrogen is always a terminal atom.

•Draw single bonds between atoms:


•Connect each atom to the central atom with single bonds (each bond represents two electrons).

•Complete the octets of outer atoms, then the central atom:


•Fill in the remaining electrons around the outer atoms to satisfy the octet rule (8 electrons per atom,
except hydrogen, which only needs 2). After the outer atoms, place any leftover electrons on the central
atom. Form double or triple bonds if needed to ensure the central atom has a full octet
Lewis dot structure
Ethylene C2H4 8+4

•Count the total valence electrons

•Determine the central atom:


H H
•Draw single bonds between atoms:
C C
H H
•Complete the octets of outer atoms, then the central atom
Bond angles
Bond angles are the angles between adjacent bonds around a central atom in a molecule. They help determine
the shape of the molecule and are influenced by the repulsions between electron pairs around the central atom.

https://chem.libretexts.org/
Bond Angle

• Carbon dioxide CO2

• sulfur dioxide SO2 119o

• sulfur trioxide SO3


120o
Formal Charge
Formal charge on atom FC = (Valence electrons)-(number of bonds to the atom)- 2(number of pair electrons).

= (Valence electrons)-1/2 (number of bonding electrons)- (number of non-bonding electrons).

Ethene
FC (C) = 4-(4)-2(0)=0 FC (0) = 1-(1)-2(0)=0

H -+
NH4Cl
FC (N) = 5-(4)-2(0)=1
H N H Cl
FC (Cl) = 7-(0)-2(4)=-1
H
Gilbert Newton Lewis

In 1916, Lewis proposed that a chemical bond consists of a pair of


shared electrons between two atoms. This concept was later
expanded by Irving Langmuir, who coined the term "covalent bond."

In 1923, Lewis redefined acids as atoms or molecules with incomplete


octets capable of accepting electrons, while bases were defined as
electron donors. Gilbert Newton Lewis’s memorandum of 1902 showing his speculations about
the role of electrons in atomic structure.
Lewis was nominated 35 times for a Nobel Prize but never won.

https://www.sciencehistory.org/

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