Brdy 6ed Ch23 OrganicPolymersAndBiochemicals

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Chapter 23:
Organic Chemistry,
Polymers, and Biochemicals
Chemistry: The Molecular Nature

of Matter, 6E
Jespersen/Brady/Hyslop
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Carbon Chemistry
Bonding
Strong covalent bonding to itself and to other nonmetal elements

Capable of forming extremely long carbon-carbon
chains
Multiple arrangements of
identical molecular formulas

lead to numerous isomers.
Chemistry: The Molecular Nature of Matter, 6E
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Structural Formula Representations

Lewis Structure of Pentane
H
H
H
Condensed Structural Formula

CH3CH2CH2CH2CH3 pentane
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Structural Formula Representations

Lewis Structure of Pentan-1-ol
Condensed Structural Formula

CH3CH2CH2CH2CH2OH 1-pentanol
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Chiral Isomers of Carbon
Chirality exists when carbon has four

unique constituents bond to itself
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Non-superimposable mirror images
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Chiral Isomers of Butan-2-ol
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Abbreviated or Bond-Line Structure
Carbon atoms occur at intersection but

no symbol used
CH3-CH2-CH3 would appear as:
Non-carbon atoms would appear as

symbols
CH3-CH2-CH2-OH would appear as:
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Open-Chain Compounds
Examples
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Abbreviated or Bond-Line Structure of

Ring Compounds
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Heterocyclic Compounds
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Learning Check
1. Draw at least two geometric isomers of C4H10

using abbreviated structures.
-Draw the four carbon chain first
-Now rearrange CH3 groups
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Your Turn!
When a chemical formula is written in the following

form, CH3CH2CH2COOH, the representation is
known as:
A. an abbreviated structure
B. a Lewis dot structure
C. a condensed formula
D. an optical isomer
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Functional Groups in Organic
Organic families can be defined by functional

groups.
Frequently use R as a place holder for
alkane-like hydrocarbon groups
R-OH
R-COOH
R-O-R
alcohol
organic acid
ether
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Functional Groups in Organic
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Learning Check
1.Write the abbreviated structure for benzoic

acid.
2. What family does C6H5NH2 belong to?
1.
2. amine family
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Your Turn!
Which of the following is an example of an ester?

A. CH3CH2CH2OH
B.
C.
D.
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Hydrocarbons
Hydrocarbon compounds only contain C and H

Alkanes
CnH2n+2
CH3CH2CH3 propane
Alkenes
CnH2n
CH3CHCH2 propene
Alkynes
CnH2n-2
CH3CCH
Aromatic
C6H6
propyne
benzene
Characterized by cyclic delocalized bonding

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Hydrocarbons
Alkanes are defined as saturated compounds.

All singles bond to carbon
Cannot add more hydrogen atoms
Alkenes and alkynes are unsaturated

compounds.
Alkenes have double bonds and H atoms can be
added to the double bond to create a saturated
compound.
Alkynes have triple bonds and H atoms can be
added to create a saturated compound.
Pt
uuuur
CH2=CHCH3 + H2
CH3CH2CH3
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Aromaticity
- Characterized by conjugated bonds in a ring such

as benzene.
- electrons are delocalized over the ring
- Leads to greater stability than expected
- Properties are different than those of other

hydrocarbon families
- Polycyclic examples:
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Hydrocarbon Nomenclature
Rules for naming alkanes

Established by IUPAC
1. Name ends in -ane
2. Complete name uses that of parent
compound with constituent groups added.
3. Parent is longest continuous carbon chain.
4. Name of longest chain based on the number
of carbons.
5. Carbon atoms are numbered starting at the
end that gives the lowest number for the
first branch.
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Straight Chained Alkanes
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Alkyl Groups
Alkane type groups added to parent chain are

known as alkyl groups. Consist of alkane,
minus one H atom. Name always ends in -yl
Example
CH4 : now remove one H which yields CH3
Naming of CH3
Start with parent name, which is methane
Drop ane and add yl
So methane becomes methyl group
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Alkyl Groups
CH3CH2CH3 yields CH2CH2CH3 when one H atom is

removed from the end carbon. The name of the aryl
group is propyl. Note, you can have another isomer
of propyl. The other isomers aryl group is 1methylethyl, or isopropyl, and is created when the H
atom is removed from the non-terminal carbon.
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Nomenclature
6. Aryl groups names are prefixed to parent

name.
7. Multiple aryl groups on a parent are
numbered and named alphabetically.
8. When there are multiple identical groups add
di, tri, tetra to the aryl name.
9. If multiple, identical aryl groups are attached
to the same carbon repeat the carbon
number.
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Examples
What is the name of the compound shown?
1. The longest carbon chain (parent) is

four. Parent name is butane.
2. Start numbering from the left to get the
smallest number for the attached group.
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Examples
3. The attached alkyl group is a methyl

group.
Thus, the correct name is:
2-methylbutane
What is the name of the following compound?
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Examples
The parent chain contains five carbons.

Thus, the parent name is pentane.
Number from the left to obtain the smallest number

for the first alkyl group.
The alkyl groups are at the 2 and 3 positions.

The 2 and 3 positions each contain a methyl group.
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Examples
Thus, the correct name is:

2,3-dimethylpentane
Lets consider an alkane with two substituents on

the same carbon.
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Examples
The parent chain is six carbons long.

The lowest correct numbering of positions is
shown below.
There are methyl and ethyl groups attached to

carbon 3.
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Your Turn!
What is the correct name for the molecule shown

below?
A. 3-butylpentane
B. 1,1-diethylpentane
C. 3-ethylheptane
D. 5-ethylheptane
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Your Turn!
What is the name of the compound shown below?
A. 3-methyl-3-methyloctane
B. 3,3-dimethyloctane
C. 2-ethyl-2-methylheptane
D. 6,6-dimethyloctane
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Chemical Properties of Alkanes

Alkanes are relatively unreactive
Not reactive in conc. NaOH or H2SO4 at room
temperature.
React with hot HNO3
Will react with Cl2 and Br2 to form halogenated
hydrocarbons.
Examples are CH3Cl, CH2Cl2 and CHCl3
Can crack molecules like ethane under controlled
conditions to form CH2CH2
Will react with O2 to form CO2, CO, and H2O
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Alkenes and Alkynes
Alkenes contain one or more double bonds

General form: CnH2n
Alkynes contain one or more triple bonds

General form: CnH2n-2
Non-polar compounds are not water soluble

Examples:
2
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Alkenes and Alkynes
Nomenclature
The parent chain must contain the multiple bond

even if it is a smaller chain length than one without
a multiple bond
Number from end that gives the lowest number to
the first carbon of the multiple bond
The number is given as -x- and placed just before
the ene or yne of the parent name. For example,
but-2-ene. The double bond starts on carbon 2 of
the chain.
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Alkene Examples
Start numbering from the left to get the lowest

number for the first carbon with the double bond
The parent is heptene and the correct naming

including the double bond location would be
hep-2-ene
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Alkene Example
The parent chain is four carbons

2,3-dimethylbut-2-ene
We would not name this 2-methyl-3-methylbut2-ene
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Naming Polyenes
How do we name compounds such as the following?
This compound contains two double bonds and is

known as a diene
We want the lowest number for the first carbon of
each of the double bonds
Start numbering from the right
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Naming Polyenes
The correct name would be hex-1,3-diene

Three double bonds would be a triene
hex-1,3,5-triene
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Cyclic Alkenes
Number ring to obtain lowest number for first

carbon of the double bond
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Cyclic Alkenes
Correct name is 1,6-dimethylcyclohex-1-ene

Other ring examples
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Your Turn!
What is the correct name for the compound shown

below?
A. 1,4-dimethylcyclopent-1-ene
B. 1,3-dimethylcyclopent-1-ene
C. 1-methyl-4-methylcyclopent-1-ene
D. 1,3-dimethylcyclo-1-pentene
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Your Turn!
What is the correct structure for 3,3-dimethylpro-1ene?
A.
B.
C.
D.
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Geometric Isomers
Groups cannot freely rotate about a double bond

Therefore, it is possible to have geometric
isomers
Examples:
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Reactions of Alkene
Alkenes readily add across the double bond

Examples of an addition reaction:
CH2CH2 + H2
Pt
CH3CH3 hydrogenation
CH2CH2 + HCl CH3CH2Cl
CH2CH2 + H2O CH3CH2OH

CH2CH2 + Cl2 CH2ClCH2Cl
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Aromatic Hydrocarbons
The most common aromatic compound is

benzene and its derivatives
Representation of bonding
Delocalized bonds create unique stability,

called resonance stabilization. The circle in the
ring represents delocalization.
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Reactions
Substitution reactions maintain benzenes

resonance structure.
Addition reactions, like those of alkenes, destroy
resonance structure
Substitution reaction:
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Addition Reaction
Notice that you have reduced the double

bonding in the ring and altered the resonance
stabilization of the ring
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Learning Check:
What product would form if benzene reacted with

nitric acid using an appropriate catalyst?
Sulfuric acid is the catalyst
A substitution reaction occurs

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Your Turn!
Which product is most likely formed when sulfuric

acid reacts with benzene?
A.
B.
C.
D.
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Organic Compounds Containing Oxygen

Important functional groups:
OH
R'
R'
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Alcohols and Ethers
Common alcohols: names end in -ol

CH3OH methanol
CH3CH2OH ethanol
CH3CH2CH2OH propan-1-ol
If the OH group was attached to the central carbon

then the alcohol would be propan-2-ol
Alcohols form hydrogen bonds, causing their boiling

points to be higher than predicted.
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Alcohols and Ethers
Primary alcohols:
Secondary alcohols:
Tertiary alcohols:
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Alcohols and Ethers
Common ethers:
CH3OCH3
dimethyl ether
CH3CH2OCH2CH3
diethyl ether
CH3OCH2CH3 methyl ethyl ether
No hydrogen bonding occurs, thus, boiling points

are lower than corresponding alcohols
Like alkanes, ethers are not very reactive
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Reactions of Alcohols
Alcohols can undergo oxidation to form a variety

of products. Oxidation removes an H atom from
the alcoholic carbon as well as the H on the OH
group.
Primary alcohols can be oxidized to aldehydes
and carboxylic acids
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Aldehydes are more readily oxidized than

alcohols
Secondary alcohols can be oxidized to ketones
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Ketones are not further oxidized

Tertiary alcohols have no H atom on the
alcoholic carbon and thus, do not undergo
oxidation
Alcohols undergo elimination reactions in the
presence of concentrated H2SO4 forming water
and alkenes
-OH group readily accepts a proton from
sulfuric acid
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Elimination Reaction
Dehydration of an alcohol
OH
H2C
H2C
H3C
H2
C
H3C
CH2
C
H
During the reaction a very unstable carbocation

is formed. This ion eliminates a proton to form
the alkene.
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Substitution Reactions of Alcohols
Using heat and concentrated HBr, HI, or HCl, a

halogen will replace the OH group
A proton adds to the OH forming OH2+

Water leaves and the halogen ion attaches to the
carbon site where the OH was attached
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Aldehydes and Ketones
Naming Aldehydes
Parent name ends in al, replacing e in the alkane

name
The aldehyde group is always at the end of a chain
and numbering starts with that end of the chain
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Naming Aldehydes
Number from the Aldehyde end

Do not use -1- for Aldehyde:
3-methylpropan-1-al, or 3-methyl-1-propanal
would be wrong
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Learning Check
What is the name of the following aldehyde?
4-ethylhexanal
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Naming Ketones
Parent name ends in one

Parent chain must contain carbonyl group
Numbering so carbonyl carbon has lowest
possible number
4-ethylheptan-3-one
NOT: 4-ethylheptan-5-one
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Your Turn!
What is the correct name for the aldehyde shown

below?
A. 2,4-dimethylpentanal
B. 2,4-dimethyl-1-pentanal
C. 2-methyl-4-methylpropanal
D. 2,4-dimethyl-5-pentanal
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Your Turn! - Solution
Aldehydes are numbered from the aldehyde end

of the molecule
There are two identical groups, (methyl) so we

use di in the naming
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Your Turn!
What is the correct name for the ketone shown

below?
A. 4-methyl-3-ethylhexan-2-one
B. 4-ethyl-3-methylhexan-5-one
C. 3-ethyl-4-methylhexan-2-one
D. 3,4-diethylpentan-2-one
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Your Turn! - Solution
Number to give lowest number to keto group so

you start from the right
Alkyl groups are ordered alphabetically so ethyl

comes before methyl
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Reactions of Aldehydes and Ketones

Aldehydes and ketones add hydrogen across the
C=O bond
Process is hydrogenation or reduction
OH
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Carboxylic Acids and Esters
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Naming Carboxlic Acids
Name ends in oic, replacing e in the parent

name
Numbering begins with carboxyl group
-COOH or -CO2H is the condensed form
CH3COOH is ethanoic acid (acetic acid)
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Naming Carboxylic Acids
Benzoic acid
OH
Propanoic acid
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Naming Esters
Name begins with alkyl group attached to the O

Name of parent acid is separate from the alkyl
group name and oic is replaced with ate
Ethyl propanate
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Learning Check
What is the name of the following ester?
Alkyl group is propyl
Number, starting with

the ester carbon
Propyl 4-methylpentanate
propyl group
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Your Turn!
What is the correct name for the product when 3methylbutan-1-ol is completely oxidized?
A. 3-methylbutanoic acid
B. 2-methyl-1-butanoic acid
C. 2-methlybutan-1-oic acid
D. 3-methylbutan-1-oic acid
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Reactions of Carboxylic Acids
The COOH is weakly acidic and therefore reacts

with base
RCOOH + OH-
RCOO- + H2O
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Formation of Esters
Esters give fruits their characteristic odor

O
OH
+ H3C
OH
H2O
ethyl pentanoate
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Saponification
Strong base reacts with an ester to form alcohol

and the esters anion forms
pentanoate ion
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Your Turn!
Name the ester formed when methanol reacts with

hexanoic acid.
A. 1-methyl hexanoate
B. methylhexanoate
C. methyl hexanoate
D. methyl hexan-1-oate
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Organic Derivatives of Ammonia

Amines are derived from ammonia with one or
more H atoms replaced with organic groups
Like ammonia, amines are weakly basic
Amines react with acids
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Acid Property of Protonated Amines

Ethylmethylammonium ion is the conjugate acid
of ethylmethylamine
H
CH3
CH3
H3C
C
H2
H2O
ethylmethylammoniun ion
pKa = 10.76
H3C
C
H2
H+
ethylmethylamine
pKb= 3.24
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Amides
General form
Where (H)R indicates either an H atom or an R

group attached
Naming
The name of the parent acid is amended dropping
the oic ending and replacing it with -amide
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Example Names of Amides
Propanamide
4-ethylhexamide
These are examples

of simple amides
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Synthesis of Simple Amides
An organic acid reacts with aqueous NH3 to form

an amide
2-methylpropanoic acid yields 2-methylpropanamide
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Amide Reactions
Amides can be hydrolyzed back to their acid

form producing ammonia in the process
OH
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Amide Reactions
Urea, an amide, ultimately hydrolyzes to NH3,

CO2 and water
Carbonic acid is formed, which then decomposes
to carbon dioxide and water
The overall reaction is:
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Basicity of Amides
Amides are not basic like amines

The lone pair on the N atom is delocalized and
thus not readily available for donation to a
proton
Amides are neutral in an acid-base sense
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Your Turn!
What is the correct name for the molecule shown

below?
O
NH2
A. 4,5-dimethylhexanamide
B. 2,3-dimethyl-6-hexanamide
C. 4-methyl-5-methylhexanamide
D. 4-isopropyl-4-methylpropanamide
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Organic Polymers
Macromolecule made up of small, repeating units

Example, polypropylene
Starting material
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Polymers
Repeating unit is called a monomer

The reaction to create a polymer is known as
polymerization
Chain Growth Polymers
Polymers created by the addition of one monomer

to another monomer
Polypropylene is an example of a chain growth
polymer
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Common Polymers
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General Repeat Unit for Polyvinyl Chloride
This unit is repeated n times to create the

polymer
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Step-Growth Polymers
Condensation reaction
A small molecule such as water is eliminated when the

monomers are joined: Nylon 6,6 example
Nylon is a copolymer, two different molecules combined
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Dacron-A Polyester
Another example of a condensation copolymer
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Physical Properties
Dependent on how polymers pack

Branching polymers create non-crystalline,
amorphous solids
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Physical Properties
Amorphous polymer of polyethylene is known as

low density polyethelene or LDPE
Low molecular mass and low structural strength
Used to make plastic grocery bags
Non-branching polyethylene forms high density
polyethylene or HDPE
Strong London forces between chains
Strong fibers are formed
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Physical Properties
HDPE is lightweight, water repellent, resists tears

Common uses
Strong mailing envelopes
Tyvek
Ultrahigh molecular weight polyethlene
3 to 6 million molar mass
UHMWPE
Used to make very strong polymers
Sails, bullet proof vests, bike helmets

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Biochemical molecules
Carbohydrates
Structures of glucose, a monosaccharide
Building unit for cellulose and starch
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Disaccharide
Sucrose
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Disaccharide Reactions
Disaccharide molecules split into

monosaccharides
Gal-O-Glu + H2O galactose + glucose
Polysaccharides
Starch is a large polymeric sugar molecule

Can be broken down into glucose, which is used for
energy in biochemical reactions
Amylose is the structurally simpler glucose polymer
portion of starch
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Disaccharide Reactions
Amylose
Amylose +n H2O
n glucose
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Polysaccharides
The majority of starch is made up of a more

complex polysaccharide known as amylopectin
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Cellulose
A polymer of glucose with different oxygen

bridge orientations
We lack an enzyme to digest cellulose
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Lipids
Water insoluble natural products

Dissolve in non-polar solvents
Relatively non-polar with large segments that are
hydrocarbon-like
Cholesterol
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Lipids
Fats and oils
Triacylglycerols-esters of glycerol and long chain

carboxylic acids (fatty acids)
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Fatty Acids
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Triacylglycerols
Triacylglycerol example
H3C
C
H2
H2
C
H
C
C
H2
HC
C
H2
CH3
C
H2
C
H2
CH3
C
H2
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Reactions of Triacylclycerols
Digestion
Breaks down the triacylclycerol into its three

component fatty acids and glycerol. Takes place in
base so in fact the fatty acids are in their anion form
Hydrogenation
The addition of hydrogen to the double bonds

Turns oils into solids
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Soap
Castile soap is made from olive oil

Olive oil has many different fatty acids
Two major fatty acid constituents are oleic acid, 5085%, and linoleic acid, 4-20%
Saponification of triacylglcerols using NaOH or other
base, and heat, results in salts of the fatty acid
components plus glycerol
Sodium oleate and sodium linoleate, for example
This product mixture, soap, is thus the result of

saponification of triacylglcerols
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Cell Membranes
Glycerophospholipids
Diacylclcerols with phosphate unit which is attached

to a amino alcohol unit
Contain a hydrophobic, water avoiding, unit and a
hydrophilic, water loving, unit
Aggregate together to form lipid bilayers with
hydrophilic layers oriented to the outside and inside
layers of the membrane
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Cell Membranes
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Cell Membranes
Membrane also contains protein units, some

which act as ion channels to move select ions in
and out of cells
Other proteins act as molecular recognition sites
for hormones and neurotransmitters
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Proteins
Polypeptides made up of -amino acids

Serve as hormones, neurotransmitters, and
enzymes
Essential amino acids are those the body does
not synthesize
Basic amino acid
structure:
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Amino Acids
Lysine
Cysteine
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Amino Acids
Isoleucine
Alanine
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Polypeptides
Formation of peptide bond

O
H3N
R'
R'
H3N
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Polypeptides
Combining two amino acids forms a dipeptide

Often the amino acids are abbreviated
Glycine - Gly
Alanine Ala
A dipeptide of these would then be shown as:

Gly-Ala
A few amino acids can be arranged in a very

large number of orders leading to many different
proteins
Gly-Ala-Arg
Gly-Arg-Ala
Ala-Gly-Arg
Plus three more
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Polypeptides and Proteins
How many ways can you arrange n different

objects?
n ! Therefore 3 amino acids have 6 arrangements
You can also use the same amino acid more than
once in a polypeptide
Proteins
Consist of polypeptides and usually small organic
molecules
They may also incorporate metal ions into their
structure
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Structure of Hemoglobin
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Nucleic Acids
RNA ribonucleic acid

DNA deoxyribonucleic acid
The chemical of a gene
Chemical basis of inherited characteristics
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Nucleic Acid Sugars
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Basic Nucleic Acid Structure

G
phosphate
Sugar
G"
G'
phosphate
sugar
phosphate
Sugar
phosphate
Where G is a placeholder for a unique nucleic

acid side chain
The sugars are ribose for RNA and deoxyribose
for DNA
The groups, G, are:
adenine (A), thymine(T), uracil(U), guanine(G), and
cytosine(C)
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DNA - Double Helix Structure
A unique arrangement of amino acids maximized

hydrogen bonding resulting in a pairing of
strands to form a double helix
Base Pairing
A only with T
C only with G
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DNA Replication
Enzyme catalyzed process unzips the two strands

Arrangement of base pairs dictates replication
pattern
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Polypetide Synthesis
Controlled formation of peptide bonds to make a

polypeptide
Repeated many times to form polypeptides and
proteins
Genetic information is transcribed from DNA in the
nucleus onto RNA (m RNA)
This messenger RNA moves outside the nucleus and
through a complex process, using other RNA types,
synthesizes a specific protein
The order of amino acid synthesis is coded so that
the correct amino acids are made available in the
proper sequence
124

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Condensed Structural Formula

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Chemistry: The Molecular Nature of Matter, 6E

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Chemistry: The Molecular Nature of Matter, 6E

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Chemistry: The Molecular Nature of Matter, 6E

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Chemistry: The Molecular Nature of Matter, 6E

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