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Chapter 23:
Organic Chemistry,
Polymers, and Biochemicals

Chemistry: The Molecular Nature


of Matter, 6E
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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.

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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
|
|
|
3
|
|
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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Abbreviated or Bond-Line Structure


Open-Chain Compounds

Examples

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Abbreviated or Bond-Line Structure of


Ring Compounds

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Abbreviated or Bond-Line Structure


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
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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'

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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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Reactions of Alcohols

Aldehydes are more readily oxidized than


alcohols

Secondary alcohols can be oxidized to ketones

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Reactions of Alcohols

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

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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-

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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

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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

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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

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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

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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
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