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Organic Chemistry:

Functional Groups
Alcohols, Carboxylic Acids &
Esters

Functional Group

A functional group is an atom, group of


atoms or bond that gives a molecule a
particular set of chemical and physical
properties

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Origin of organic compounds
Naturally occurring organic compounds are
found in plants, animals, and fossil fuels
All of these have a plant origin
All of these rely on the fixing of C from CO 2
Synthetic organic compounds are derived
from fossil fuels or plant material
Introduction
Most current research focuses on Organic
Originally from organic meaning life
Not just chemistry of life, chemistry of carbon
Exceptions:
oxides of carbon (CO2, CO)
carbonates,bicarbonates(NaHCO3,CaCO3)
cyanides (NaCN, etc)

One C with no H, or with metal C C C


Carbon can form four bonds
C C
Organic Chemistry
Organic chemistry is the chemistry of carbon.
There are three forms of pure carbon

Diamond

Graphite

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Organic Chemistry
Organic chemistry is the chemistry of carbon.
There are three forms of pure carbon

Buckminsterfullerene
Bucky Balls

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Carbon forms four bonds
Carbon can form four bonds, and forms
strong covalent bonds with other elements
This can be represented in many ways
O Cl CH3 CH3
H Cl
C C CH C
H3C CH3
C C Cl C CH
CH3 CH3
H H CH CH

CH2 CH2 CH2 CH2 CH3


H3C CH2 CH2 CH2 CH2
Functional groups
Functional groups are parts of molecules that
result in characteristic features
About 100 functional groups exist, we will
focus on about 10
Useful to group the infinite number of
possible organic compounds
E.g. the simplest group is hydrocarbons
Made up of only C and H
Not really a functional group
Further divided into:
Alkanes, Alkenes, Alkynes, Aromatics
Classifying organic compounds
Hydrocarbons
Alkanes C C Alkenes C C
H H H H H H H H
H C C C C C H H C C C C C H
H H H H H H H H H H

Alkynes C C Aromatics H
H C H
H H H C C
H C C C C C H C C
H C H
H H H
H
Alkanes
H H
All bonds are single
Saturated H C C H
No new bonds can be added
General formula CnH2n+1 H H
Summary of types
Naming organic compounds
Meth - ane

Number of Type of
carbon compound
atoms
alkenes

Only carbon and H H


hydrogen
A carbon to carbon C C
double bond
H H
Saturation bonding:
Multiple bonds and unsaturation
Saturated: no more bonds can be added
Unsaturated: more bonds can be
formed
More reactive compounds
Alkenes, Alkynes & Aromatic Compounds
The remaining three families of hydrocarbons are
unsaturated.

Alkanes are saturated, which means they contain the


maximum number of hydrogens per carbon.
For alkanes CnH(2n+2)

Alkenes, Alkynes and Aromatics are unsaturated, which


means they contain less than the maximum number of
hydrogens per carbon.
Structurally, this means that they have carbon-carbon double or triple bonds

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Alkenes contain double bonds
Examples of alkynes
Cycloalkanes
When there are three or more carbons in a straight chain, the
ends can be joined to make rings.

In naming these molecules, the prefix cyclo- is used to


indicate the ring:

Skeletal structural formulas are used to represent the rings


in structural formulas:

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Cycloalkanes
In naming these molecules, the prefix cyclo- is used to
indicate the ring:
As Parent Chain As Substituent Group

C3H6
cyclopropane R cyclopropyl-

C4H8
cyclobutane R cyclobutyl-

C5H10

cyclopentane R cyclopentyl-

C6H12
R
cyclohexane cyclohexyl-
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Cycloalkanes
The carbon-carbon single bonds for the carbons in a ring are
no longer free to rotate.
This leads to a new type of isomer
Since the two structures share the same name, they are
not constitutional isomers.
CH3 CH3 CH3 CH3
1,2-dimethylcyclohexane 1,2-dimethylcyclohexane
H H H H
H H H
H H H H
H H CH3 H
H H H H
CH3 CH3 H CH3

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Cycloalkanes
Isomers which share the same atomic connections, and
therefore, the same IUPAC name are called stereoisomers.
When this occurs due to restricted rotation about a
covalent bond, they are called geometric isomers
The prefix cis- and trans- are used to distinguish geometric
isomers.
CH3 CH3 CH3 CH3
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane
H H H H
H H H
H H H H
H H CH3 H
H H H H
CH3 CH3 H CH3

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Aromatic: the stuff of dreams
Benzene ring contains 6 C atoms
Bonding is resonant more stable than
expected
All aromatic compounds contain at least
one benzene ring
Benzene, C6H6, is one of the most important
industrial chemicals
Toxicity of benzene
Benzene is regarded as a highly
carcinogenic substance
Use and disposal of benzene are regulated
Compounds containing benzene rings are
not necessarily toxic
Alkenes, Alkynes & Aromatic Compounds
Naming of Aromatics is based on benzene:
When the molecule is build on benzene, the parent name
is benzene.
There are also many common names used to describe
aromatic compounds.

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Alkenes, Alkynes & Aromatic Compounds
Naming of Aromatics is based on benzene:
Aromatic compounds can contain multiple aromatic rings

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Alkenes, Alkynes & Aromatic Compounds
Benzo(a)pyrene found in tobacco smoke is converted to
carcinogenic products in the liver (see below) which link to
DNA and cause mutations.

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Functional groups
Chemistry of organic compounds is
determined by functional groups
Functional group is an atom or group of
atoms that are different from C
Heteroatoms confer very different
properties on the substance
Heteroatoms affect physical and
chemical properties
C2H6 (ethane) is a gas at RT
C2H6 is insoluble in water
C2H6O (ethanol) is a liquid at RT
C2H6O is soluble in water
Differences in cohesive forces: O-H bonds are
polar, C-H bonds are not
Functionalized hydrocarbons
Chlorocarbons and the environment

Important uses important problems


Solvents CH2Cl2
Insecticides DDT
Refrigerants CFCs
Alcohols, Carboxylic Acids & Esters
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Carboxylic acids
Members of the carboxylic acid family contain a
carboxylic acid group
The carboxylic acid group comprises a hydroxyl group
connected to a carbonyl group:

O O

C + O H C O H
carbonyl group hydroxyl group carboxylic acid group

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Alcohols
Functional group OH
Polar molecules dissolve in H2O
Ethanol: good for your health/bad for your
health? H H

H C C O H

H H
Smoke gets in my eyes: olefactory
pleasures of aldehydes
H
C=O is carbonyl group
Aldehyde contains RCHO H C C O

Formaldehyde is a preservative and a H H


product of burning wood
Acrolein is a product of barbequing
Common smells and flavours
Ketones
Ketone is R1R2CO
Acetone is a common solvent
Smell found in cinnamon
Raspberries
Carboxylic acids
Commonly found in citrus fruits and any
sour foods
Formic acid present in ant and bee stings

H O

H C C O H

H
Esters: sweet aromas and flavours

Ester group is R1COOR2


Sweet aroma in pineapples, jasmine
Synthetic versions are very common
H O H

H C C O C H

H H
Alcohols, Carboxylic Acids & Esters
Examples of some
flavorable esters:

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Ethers
Ethers contain R1-O-R2
No -OH bonds
Not soluble in water
Anesthetics
Amines: the stench of death
Amines contain NR1R2R3
Rotting fish
Decaying flesh
Illicit drugs
Molecule in the News:Melamine

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Hydroxyl, carbonyl, carboxyl
There are other names that describe patterns
of atoms that are parts of functional groups.
Hydroxyl refers to OH
Carbonyl refers to C=O
Carboxyl refers to COOH
Q: which functional groups contain a hydroxyl
group? A carbonyl group? A carboxyl group?
Hydroxyl: alcohols, carboxylic acids. Carbonyl:
aldehydes, ketones, carboxylic acids, amides,
esters. Carboxyl: carboxylic acids
Note that properties such as boiling and melting
point change due to functional groups For more lessons, visit
www.chalkbored.com