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[SCH4U]Introduction to Organic Chemistry

Introduction to Organic Chemistry
by

Michael Suh

on 9 May 2017

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Transcript of [SCH4U]Introduction to Organic Chemistry

Hydrocarbon that has 1.5 bonds between carbons in hexagonal ring structure. (Resonance structure)
Special nature of bonds between carbons reinforce the structure of the molecule to be flat, not a chair/boat form.
Characterized by strong aroma, it is known to be aromatic hydrocarbon.
Types of Organic Molecules
1. Hydrocarbon
(i) Alkane
(ii) Alkene
(iii) Alkyne
(iv) Aromatic hydrocarbon
2. Alcohol
3. Aldehyde
4. Ketone
5. Carboxylic Acid
What is Organic Chemistry?
Organic Chemistry is study of matters of living organisms. This includes:
- Carbohydrate
- Lipid
- Protein
- Cellulose
- DNA
- Vitamins + Minerals
Welcome to
the World of Organic Chemistry!

Things to know before you study
Organic Chemistry...
1. Definition of atom, molecule and their structures

2. Types of bond, bonding behaviour of atoms

3. Types of Chemical Reactions
What's to Learn in Organic Chemistry?
1. Definition
2. Basic Structure of Carbon atom and structural variation (isomer)
3. Naming Organic Molecules using IUPAC system
- Simple hydrocarbon: alkane, alkene, alkyne, cyclic hydrocarbon, aromatic hydrocarbon (benzene)
- Hydrocarbon derivative: alcohol, haloalkane, ketone, carboxylic acid, ester, ether, amine, amide
4. Chemical&Physical Properties of Orgnanic Molecules
5. Reactions of Organic Compounds (Chapter 2)
6. Organic molecules in living system (Chapter 2)
Review: Chemistry
1. Atomic model

2. Atoms to Molecules

3. Chemical Reactions
Unit 2: Organic Chemistry
[SCH4U]Chemistry 12
All have hydrogen + carbon 'backbone' structure
Common Characteristics to all Organic Molecules
Atomic Model
-> Number of neutrons and protons vary: charged atoms & isotopes
- Nucleus (Proton [+], Neutron [0]) & Electron [-]
- Planetary model
- Atomic number = Number of Protons
- Positive & negative charges of protons and electrons attract each other enabling electrons to stay in the orbit
- Atoms combine in different connectivity and ratio, resulting in various molecules with different shape and properties
Atoms to Molecules
- Types of bond
(i) Covalent bond: "Sharing electrons" to satisfy Octet Rule -> Molecular Compound

(ii) Ionic bond: "Give and Take" between two atoms incurring charges on atoms involved in bonding
-> Ionic Compound
Octet Rule: An atom will be most stable when there are 8 valence electrons
Chemical Reactions
There are four kinds of chemical reactions:
(i) Synthesis reaction
e.g. A + B -> C
(ii) Decomposition reaction
e.g. A -> B + C
(iii) Single Displacement
e.g.
A
B + C -> AC + B
(iv) Double Displacement
e.g. AB + CD -> AD + BC
General characteristics of organic molecules
Special Nature of the Carbon Atom
- 4 valence electrons
- 'medium' nucleus strength to attract electrons (electronegativity)
- capable of forming 4 bonds (mostly covalent bond)
- mostly form symmetrical molecule allowing it to be a stable backbone for hydrocarbon molecules
Isomers
(i) Constitutional isomers: same molecular formula with variation in sequence
(ii) Stereoisomers: same molecular formula and sequence with variation in 3D orientation
(i) Constitutional Isomers
- Same number of atoms in molecules but different sequence
- may be more than two isomers
- exhibit distinct properties and different behaviours during chemical reaction
(ii) Stereoisomers
- Same number of atoms in molecules and same sequence but different orientation in 3D space
- may be more than two isomer
- exhibit distinct properties and different behaviours during chemical reactions
a. Diastereomers
- Resulting from the presence of double bond
- cis isomer: two identical molecules located on the same side of double bond
- trans isomer: two identical molecules located on the opposite side of double bond
b. Enantiomers
- identical number of atoms, sequence but mirror image of each other
- exhibit very similar physical properties due to similarity in their structures but shows difference in chemical reactions
- Mirrors image: two isomers are not superimposable
Types of Hydrocarbon Chains
Alkane: Saturated Hydrocarbon
Alkene: Double bond, Unsaturated
Alkyne: Triple bond, Unsaturated
Cyclic Alkane: Ring structure
Aromatic hydrocarbon: Phenol
Alkane: Saturated
Why is it called "Saturated" hydrocarbon?
Alkene: Unsaturated Hydrocarbon
Hydrocarbon chain with at least one double bond between carbon-carbon
Alkyne: Triple bond
Hydrocarbon chain with at least one triple bond between carbon-carbon
Cyclic Hydrocarbon
Hydrocarbon chains in a ring structure, that may or may not contain double or triple bond.
Aromatic Hyrdrocarbon
Hydrocarbon purely consist of carbons and hydrogen atoms.
Entire molecule consists of single bond between carbon and hydrogen atoms.
No more room for additional bond (i.e. Saturated)
Naming Hydrocarbon molecules
1. Find the longest carbon chain. This is the parent chain of the molecule
2. Count the number of carbons in the parent chain.
3. Identify all substituents group (carbon chains in a molecule that are not a part of parent chain)
4. Use the table to identify the name of parent chain and substituent groups.
5. Number the carbons on the parent chain such that the location number for substituents group is lowest possible number.
Double bond may undergo an addition reaction to add more atoms to the carbon
Not Saturated yet!
Triple bond between carbons may undergo an addition reaction and can have more bond on the carbon
Unsaturated!
Alkane chain variations
(i) Alkane chain with branches (substituents groups)

(ii) Cyclic alkane

(iii) Alkyl halide (haloalkane)
(i) Alkane with Alkyl substituents
Q: Name the following molecule.
Number of carbons: 7
Root name: Heptane
Is there any branch? No
the name of the molecule is heptane.
Name the following molecule
Number of carbon: 8
Root name: octane?
NO!!
Find the longest hydrocarbon chain -> parent chain
7 carbon chain = heptane
CH3? -> Substituent group
CH3- = methyl group is located on third carbon on the parent chain
The name of the molecule is 3-methyl heptane
What if there is more than one branch?
-> identify each as a substituent group and location by numbering the carbon atoms.
-> If more than one numbering is possible, choose the one that result in the lowest possible numbering.
2,5-diethyl-6-methyl octane
not 4,7-diethyl-3-methyl octane!
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