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UNIT 1: Organic Chemistry
Chapter 1: Structure and Physical
Properties of Organic Compounds
Chapter 2: Reactions of Organic
Compounds
UNIT 1 Chapter 2: Reactions of Organic Compounds
Chapter 2:
Reactions of Organic Compounds
Chemical reactions of organic
compounds have provided an
abundance of products we rely
on. However, the properties
that make them so useful can
also cause environmental
problems.
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The Plastika sailboat was built from
plastic bottles to raise awareness of
plastic pollution in ocean ecosystems.
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
2.1 Types of Organic Reactions
Organic reactions can convert simple organic molecules
into large, complex ones.
TAXOL is an anti-cancer
drug that chemists can
synthesize.
Important types of organic reactions:
• addition
• elimination
• substitution
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• condensation
• esterification
• hydrolysis
• oxidation
• reduction
• combustion
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Addition Reactions
•
•
•
•
Reactions between an alkene or alkyne and a small
molecule (HOH, H2, HX, X2)
Atoms of a small molecule are added to carbons of a
double or triple bond
Reactions of alkynes can produce alkenes or alkanes
Constitutional isomers may form
Carbon atoms of the
multiple bond have more
atoms bonded to them in
the product.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
LEARNING CHECK
Show how constitutional isomers can
form from the following reaction.
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
The chlorine atoms can be added to
either carbon 2 or 3 in this addition
reaction.
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Addition Reactions (cont’d)
One constitutional isomer will predominate.
To predict the major product:
Markovnikov’s rule:
The hydrogen atom of the small molecule will attach to the
carbon atom of the double bond that is bonded to the most
hydrogens.
The 2-chloropropane
isomer will be the
major product.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Elimination Reactions
•
•
•
Two atoms bonded to carbon atoms of an organic
molecule are removed and a double bond forms
The double bond forms between the carbon atoms that
have had the atoms removed
Elimination reaction can be thought of as the reverse of
an addition reaction
Carbons of the organic
product are bonded to
fewer atoms than carbons
of the reactant.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
LEARNING CHECK
Draw the product of the following
elimination reaction.
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
The product formed is:
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Elimination Reactions (cont’d)
What if an asymmetric molecule undergoes elimination?
General rule:
The hydrogen atom is more likely to be removed from the
carbon atom with the most C-C bonds.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Substitution Reactions
•
•
•
Reaction in which a hydrogen or functional group has
been replaced by another functional group
Two compounds react to form two different compounds
The same number of atoms are bonded to the carbon
atoms of the reactants and products
Two compounds are
converted to two new
compounds.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
LEARNING CHECK
Draw the products of the following
substitution reaction.
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
The products formed are:
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Condensation Reactions
•
•
•
Two molecules combine to produce a larger organic
molecule and another much smaller molecule
Water is often the smaller molecule formed
Large biomolecules (DNA, fats, carbohydrates, protein)
are formed through this type of reaction
A condensation reaction
between a carboxylic acid
and an amine produces
an amide.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Esterification Reactions
•
•
These are a type of condensation reaction
A carboxylic acid and an alcohol react to produce an
ester and water
In what way(s) is an esterification reaction like a
condensation reaction?
An esterification reaction
is between a carboxylic
acid and an alcohol.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Hydrolysis Reactions
•
•
•
A molecule is broken apart through the addition of a
water molecule (HOH)
The –OH is added to one side of a bond, and the H is
added to the other side of the bond
They are the reverse of condensation reactions
In hydrolysis reactions,
molecules are broken
apart using water as a
reactant.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
LEARNING CHECK
What are the products of the following
reaction?
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
This is an esterification reaction.
The products are:
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Oxidation Reactions
• In organic chemistry, the term refers to carbon atoms of
the organic reactant
• forming more bonds to oxygen atoms, or
• forming fewer bonds to hydrogen atoms
•
Common oxidizing agents, [O], are KMnO4 and
K2Cr2O7
Compare the number of C-H and C-O bonds in the reactant and product.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Reduction Reactions
• In organic chemistry, the term refers to carbon atoms of
the organic reactant
• forming fewer bonds to oxygen atoms, or
• forming more bonds to hydrogen atoms
•
Common reducing agents, [H], are LiAlH4 and H2/Pt
Compare the number of C-H and C-O bonds in the reactant and product.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
Combustion Reactions
•
•
•
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A compound reacts with oxygen to produce oxides of
the component elements
The products of the complete combustion of a
hydrocarbon are carbon dioxide and water
If O2 is insufficient, incomplete combustion occurs
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1
LEARNING CHECK
What is the product of the following
reaction?
+ [H]
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
The reaction is a reduction of
propanone (acetone) to produce
propan-2-ol (isopropanol)
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.1 Review
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Section 2.1
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
2.2 Polymer Equations
Polymers are very large molecules of repeating monomers.
• Some are made of one type of monomer
• Some are made up two or more types of monomers
• Most are named based on the monomer(s)
This polymer is
made of two
different
monomers.
• Natural polymers: cotton, wool, protein, DNA
• Synthetic polymers: plastics, polyester, nylon, rayon
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
Addition Polymerization
• Synthetic polymers can be made using the addition
reaction
• Alkene monomers are joined together through multiple
addition reactions
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
Condensation Polymerization
• Synthetic polymers can be made using the condensation
reaction
• Monomers are joined together through multiple reactions
between two different functional groups on different
monomers
polyamide
polyester
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
LEARNING CHECK
Identify the monomer(s) of the
polymer shown below.
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
The monomer is ethene, H2C=CH2
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Section 2.2
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
Polymers and Industry
• Many industrial productions of polymers start with
petroleum (mix of hydrocarbons)
• Hydrocarbons of the petroleum are converted to
petrochemicals for synthetic reactions (e.g., ethene and
propene)
The Manufacture of PVC
ethene
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1,2-dichloroethane
vinyl chloride
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
Polymer Production: Risks and Solutions
The manufacture of synthetic polymers has given us many
useful and life-saving products, but synthetic polymers
come with serious risks, such as
• Workers’ exposure to dangerous chemicals
• Leaching or release of dangerous chemicals
• Very slow degradation in the environment
What are some possible solutions?
Fleece fabric can be produced from the plastic of soft drink bottles.
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UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
Natural Polymers
• There are numerous examples of natural polymers,
including ones that are essential for life
• Example of biologically important polymers are
polysaccharides, proteins, and DNA
polysaccharides
• contain sugar monomers
• include starch, cellulose
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Cellulose provides structure to
plants. It is composed of
glucose monomers.
UNIT 1 Chapter 2: Reactions of Organic Compounds
Natural Polymers (cont’d)
Proteins
• build muscle
• act as catalysts in cells
(enzymes)
Proteins are amide-linked
polymers of amino acids.
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Section 2.2
UNIT 1 Chapter 2: Reactions of Organic Compounds
Natural Polymers (cont’d)
DNA
• genetic material
DNA is composed of nucleotide
monomers.
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Section 2.2
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2
LEARNING CHECK
Explain why your genetic material
(DNA) and soft drink bottle material
(PET) are classified as the same type
of molecule.
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Answer on
the next slide
UNIT 1 Chapter 2: Reactions of Organic Compounds
LEARNING CHECK
Both are polymers. Both are made
of repeating units of monomers.
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Section 2.2
UNIT 1 Chapter 2: Reactions of Organic Compounds
Section 2.2 Review
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Section 2.2