Functional Groups - Organic Chemistry

Organic Chemistry

Introduction
Functional Groups
Alkanes
Alkenes
Alkynes
Alcohols
Acids, Esters and Amides
Introduction

 Organic chemistry is the study of carbon-

containing compounds
 especially compounds containing C-C bonds
 The field of organic chemistry is very important

for a wide variety of reasons.
 A huge number of carbon-containing
compounds are known.
 More than 16 million known compounds
 About 90% of new compounds made each
year contain carbon
Introduction
 Most of the advances in the pharmaceutical

industry are based on a knowledge of
organic chemistry.
 Many drugs are organic compounds
 Life as we know it is based on organic
chemistry.
 Most biologically important compounds
contain carbon:
 DNA, RNA
 proteins
 carbohydrates
Introduction
 Learning organic chemistry requires you to
integrate and apply many of the concepts
you’ve learned in general chemistry:
Electron configuration Acid/base reactions

Valence bond theory Oxidation/reduction
Lewis structures Kinetics
Resonance structures Equilibrium
Hybrid orbitals Thermodynamics
Molecular geometry Stoichiometry
H O H O
H CIntroduction
C O H H C C O H
H
 Some H
familiar organic compounds:
H H H H
H C H H C C C H
H H H H
methane propane
H O H
H C C H
H C C C H
acetylene H H acetone
Introduction
 Some familiar organic compounds:
H O H H H H
H C C O H H C C O C C H
H Acetic acid H H H H
“ether”
H H O
H C C O H C OH aspirin
H H Ethyl alcohol O C CH3

O
Introduction
 Most organic compounds have a “skeleton”

that is composed of C-C bonds.
 The C-C bonds may be single bonds,
double bonds, or triple bonds.
 The “skeleton” of an organic compound has

H’s attached to it.
 other “heteroatoms” like O, halogens or N
may be present as well
Introduction
 The number of bonds formed by C in an
organic compound is determined by the
electron configuration of C.
 Carbon has four valence electrons:

1s22s22p2
Introduction
 Carbon generally forms 4 equivalent bonds.
 The formation of four equivalent bonds is

best explained using the concept of hybrid
orbitals.
Introduction
 The structure of an organic compound can
be predicted by drawing a Lewis structure:
H O H
H C C C H acetone
H H
Introduction
 In organic molecules, we generally describe
the geometry around each carbon atom.
 Geometry is predicted using:

 VSEPR
 hybrid orbitals
Introduction
 When C forms four single bonds:

 sp3 hybrid orbitals are involved
 tetrahedral geometry
H H
 When C forms a double bond: C C
H H
 sp2 hybrid orbitals are used
 trigonal planar geometry
 When C forms a triple bond:

 sp hybrid orbitals are used
 linear geometry
H C C H
Introduction
Example: Identify the electron domain
geometry and hybrid orbitals used by each
atom (except hydrogen) in the following
compound.
H O
H C C C C O H
H
Introduction
 Organic compounds contain not only C-C
bonds but also C-H bonds.
 C-C and C-H bonds tend to be non-polar

because there is a small difference in
electronegativites
 Most (but not all) organic compounds are

relatively non-polar
generally not very soluble in water
Hydrocarbons
 The simplest organic compounds are the
hydrocarbons:
 organic compounds that contain only
carbon and hydrogen
 four general types:

alkanes
alkenes
alkynes
aromatic hydrocarbons
Hydrocarbons
 Alkanes:
 hydrocarbons that contain only single
bonds
 Examples:
 Methane CH4
 ethane H H
H–C–C–H
H H
Hydrocarbons
 Alkenes:
 hydrocarbons that contain a C = C double
bond
 H2C = CH2 (ethylene)
 Alkynes:
 hydrocarbons that contain a C C triple
bond
 H – C C – H (acetylene)
Hydrocarbons
 Aromatic hydrocarbons:
 contain a planar ring structure in which
the carbon atoms are connected by a
combination of both  and  bonds
H
C
H-C C-H
benzene
H-C C-H
C
H
Introduction
 Organic compounds that are soluble in polar
solvents such as water generally have a polar
functional group present in the molecule.
 An atom or group of atoms that influences
the way the molecule functions, reacts or
behaves.
 an atom or group of atoms in a molecule that
undergoes predictable chemical reactions
 the center of reactivity in an organic
molecule
Introduction
 Functional groups that contain O or N atoms
often lead to a polar organic molecule
 large difference in electronegativity
C vs. O
C vs. N
 Examples of familiar polar organic compounds:

 glucose
 acetic acid
Functional groups
 Vitamin C
contain C-O bonds
 amino acids
Functional groups contain
C-O and C-N bonds
Functional Groups
 Since functional groups are responsible for
the many of the chemical and physical
properties of organic compounds, we often
classify and study organic compounds by
the type of functional group present.
 On your exam, you will be responsible for

recognizing and naming the various common
functional groups that are found in organic
compounds:
Functional Groups
Functional Type of
Group Compound Example
C=C alkene H2C = CH2
C C alkyne HC CH
C–O–H alcohol CH3OH
C–O–C ether CH3CH2OCH2CH3
C–N amine CH3NHCH3
Functional Groups
Functional Type of
O O
C–H aldehyde CH3C – H
O O
C–C–C ketone CH3 – C – CH3

Functional Groups
Functional Type of
O O
Carboxylic
C–O–H acid CH3C – O – H
O O
C–O–C ester CH3C – O – CH2CH3

Functional Groups
Functional Type of
O O
C–N– amide CH3C – N – CH3
H
Functional Groups
Example: Name the functional groups that are
present in the following compounds:
CH3CH2OH
O
H2C = CHCOH
CH3CH2NCH3
CH3
Functional Groups
Example: Name the functional group(s) that is (are)
present in the following compounds:
O
H2C CH2
H2C CH2
CH3NHCH2CH2OCH3
Hydrocarbons
 Alkanes are often called saturated
hydrocarbons
 they contain the largest possible number
of hydrogen atoms per carbon atom.
 Alkenes, alkynes, and aromatic

hydrocarbons are called unsaturated
hydrocarbons
 they contain less hydrogen than an alkane
having the same number of carbon atoms
H H H H
Alkanes H C C C C H
H H H H
 Organic compounds can H H
be Hrepresented
H in
many different ways:H C C C C H
H H H
H
 molecular formula: C4H10H H H H
(butane)
 Lewis structure: H H H
H C HC C C H
H C C C C H
H HH H H H
H H
 Condensed structural formula
 CH3CH2CH2CH3
 Line angle drawings
Alkanes
Some of the simplest alkanes:
Condensed
Formula Name
CH4 methane
CH3CH3 ethane
CH3CH2CH3 propane
CH3CH2CH2CH3 butane
CH3CH2CH2CH2CH3 pentane
You must know these!!!

Alkanes
Some of the simplest alkanes:
Condensed
Formula Name
CH3CH2CH2CH2CH2CH3 hexane
CH3CH2CH2CH2CH2CH2CH3 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane
You must know these!!!
Alkanes
 The previous alkanes are also called
straight-chain hydrocarbons:
 all of the carbon atoms are joined in a
continuous chain
 Alkanes containing 4 or more carbons can

also form branched-chain hydrocarbons
(branched hydrocarbons)
 some of the carbon atoms form a “branch”
or side-chain off of the main chain
Alkanes
 An example of a straight chain hydrocarbon:
 C5H12 CH3CH2CH2CH2CH3 pentane
 Examples of a branched hydrocarbon:
 C5H12 CH3CHCH2CH3 CH3
CH3 CH3CCH3
2-methylbutane
CH 3
2,2-dimethylpropane
Alkanes
 The three structures shown previously for
C5H12 are structural isomers:
 compounds with the same molecular
formula but different bonding
arrangements
 Structural isomers generally have different

properties:
 different melting points
 different boiling points
 often different chemical reactivity
Alkanes
 Alkanes with three or more carbons can also
form rings or cycles.
 Cycloalkanes:
 Alkanes containing a ring structure that is
held together by C – C single bonds
 Examples: CH2
H2C CH2
cyclopropane
Alkanes
 Examples of cycloalkanes:
CH2
H2C CH2 cyclopentane
H2C CH2
CH2
H2C CH2
cyclohexane
H2C CH2
CH2
Alkanes
 Organic compounds can be named either
using common names or IUPAC names.
 You must be able to name alkanes, alkenes,

alkynes, and alcohols with 10 or fewer
carbons in the main chain using the IUPAC
naming system.
Alkanes
 Alkane Nomenclature:
 Find the longest continuous chain of
carbon atoms and use the name of the
chain for the base name of the compound:
longest chain may not always be written
in a straight line
1 2
CH3 - CH - CH3 Base name:
hexane
3 CH - CH2 - CH2 - CH3
2 4 5 6
Alkanes
 Number the carbon atoms in the longest
chain beginning with the end of the chain
closest to a substituent
groups attached to the main chain that
have taken the place of a hydrogen
atom on the main chain
1 2 A substituent
CH3 -2CH - CH3
3 CH - CH2 - CH2 - CH3
2 4 5 6
Alkanes
 Name and give the location of each
substituent group
A substituent group that is formed by
removing an H atom from an alkane is
called an alkyl group:
 Name alkyl groups by dropping the “ane”

ending of the parent alkane and adding
“yl”
Alkanes
 Common alkyl groups (substituents):
CH3 methyl
CH3CH2 ethyl Know
CH3CH2CH2 propyl these!
CH3CH2CH2CH2 butyl
1 2
CH3 -2CH - CH3
2-methylhexane
3 CH - CH2 - CH2 - CH3
2 4 5 6
Alkanes
 Halogen atoms are another common class

of substituents.
Name halogen substituents as “halo”:
Cl chloro
Br bromo
I iodo
Alkanes
 When two or more substituents are present,
list them in alphabetical order:
 Butyl vs. ethyl vs. methyl vs. propyl
 When more than one of the same substituent

is present (i.e. two methyl groups), use
prefixes to indicate the number:
 Di = two
 Tri = three
 Tetra = four Know these.
 Penta = five
Alkanes
Example: Name the following compounds:
CH3CH2CHCH2CH3
CH3
CH2CH2CH3
CH3CHCHCH3
CH3
Alkanes
CH3CH2CHCH3
CH2CH2Br
CH2CH2CH3
CH3CHCHCH3
Cl
Alkanes
 You must also be able to write the structure
of an alkane when given the IUPAC name.
 To do so:
 Identify the main chain and draw the
carbons in it
 Identify the substituents (type and #) and
attach them to the appropriate carbon
atoms on the main chain.
 Add hydrogen atoms to the carbons to
make a total of 4 bonds to each carbon
Alkanes
Example: Write the condensed structure for
the following compounds:
3, 3-dimethylpentane
3-ethyl-2-methylhexane
2-methyl-4-propyloctane
1, 2-dichloro-3-methylheptane
Alkenes
 Alkenes:
 unsaturated hydrocarbons that contain a
C=C double bond
 Alkene Nomenclature:
 Names of alkenes are based on the
longest continuous chain of carbon atoms
that contains the double bond.
Alkenes
 Alkene Nomenclature
 Find the longest continuous carbon chain
containing the double bond.
 Change the “ane” ending from the

corresponding alkane to “ene”
 butane butene
 propane propene
 octane octene
Alkenes
 Indicate the location of the double bond using
a prefix number
designate the carbon atom that is part of the
double bond AND nearest to the end of the
chain
 Name all other substituents in a manner

similar to the alkanes.
 Use a prefix to indicate the geometric isomer

present, if necessary.
Alkenes
 Different geometric isomers are possible for

many alkenes.
 Compounds that have the same molecular
formula and the same groups bonded to
each other, but different spatial
arrangements of the groups
cis isomer
trans isomer
Alkenes
 Cis isomer:
two identical groups (on adjacent
carbons) on the same side of the C = C
double bond
 Trans isomer:
two identical groups (on adjacent
carbons) on opposite sides of the C = C
double bond
Alkene
CH3 CH3 CH3 H

C=C C=C
H H H CH3
cis-2-butene trans-2-butene
Alkene
For an alkene with the general formula
A P
C=C
B Q
cis and trans isomers are possible only if
A = B and
P=Q
Alkene
Example: Name the following alkenes:
CH3CH2 H
C=C
H H
CH3CH2 H
C=C
CH3CHCH2 CH2CH3
CH3
Alkenes
Example: Draw the structures for the following
compounds:
2-chloro-3-methyl-2-butene
trans-3, 4-dimethyl-2-pentene
cis-6-methyl-3-heptene
Alkynes
 Alkynes:
 unsaturated hydrocarbons that contain a
C C triple bond
 Alkyne Nomenclature:
 Identify the longest continuous chain
containing the triple bond
 To find the base name, change the ending

of the corresponding alkane from “ane” to
“yne”
Alkynes
 Alkyne Nomenclature:
 Use a number to designate the position of
the triple bond
number from the end of the chain
closest to the triple bond
just like with alkenes
 Name substituents like you do with

alkanes and alkenes
Alkynes
CH3CH2C CCHCH3
CH2CH3
CH2CH2C CH
Cl
Alkynes
Example: Draw the following alkynes.
4-chloro-2-pentyne
3-propyl-1-hexyne
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Organic Chemistry

 Organic chemistry is the study of carbon-

 The field of organic chemistry is very important

 Most of the advances in the pharmaceutical

Electron configuration Acid/base reactions

H H Ethyl alcohol O C CH3

 Most organic compounds have a “skeleton”

 The “skeleton” of an organic compound has

 Carbon has four valence electrons:

 The formation of four equivalent bonds is

 Geometry is predicted using:

 When C forms four single bonds:

 When C forms a triple bond:

 C-C and C-H bonds tend to be non-polar

 Most (but not all) organic compounds are

 four general types:

 H2C = CH2 (ethylene)

 Examples of familiar polar organic compounds:

 On your exam, you will be responsible for

C–H aldehyde CH3C – H

C–C–C ketone CH3 – C – CH3

C–O–C ester CH3C – O – CH2CH3

C–N– amide CH3C – N – CH3

 Alkenes, alkynes, and aromatic

You must know these!!!

 Alkanes containing 4 or more carbons can

 C5H12 CH3CH2CH2CH2CH3 pentane

 Examples of a branched hydrocarbon:

 C5H12 CH3CHCH2CH3 CH3

 Structural isomers generally have different

 You must be able to name alkanes, alkenes,

 Name alkyl groups by dropping the “ane”

 Halogen atoms are another common class

 When more than one of the same substituent

 Change the “ane” ending from the

 Name all other substituents in a manner

 Use a prefix to indicate the geometric isomer

 Different geometric isomers are possible for

CH3 CH3 CH3 H

 To find the base name, change the ending

 Name substituents like you do with

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