Organic Chemistry
 Introduction
 Functional Groups
 Alkanes
 Alkenes
 Alkynes
 Alcohols
 Acids, Esters and Amides
Introduction
 Organic chemistry is the study of carbon-
containing compounds
 The field of organic chemistry is very
important for a wide variety of reasons.
 A huge number of carbon-containing
compounds are known.
 Most of the advances in the pharmaceutical
industry are based on a knowledge of organic
chemistry.
 Life as we know it is based on organic
chemistry.
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.
 Carbon forms a total of 4 bonds.
 The “skeleton” of an organic compound has H’s
attached to it.
 other “heteroatoms” like O, halogens, N,
S, and P may be present as well
H O
Introduction
C
C O H
H
H O
H C C O H
 Some
familiar organic compounds:
H
H
H
H C H
H
H H H
H C C C
H
H H H
propane
methane
H O H
H C C H
acetylene
H C C
H
C
H
H acetone
Introduction
 Some familiar organic compounds:
H O
H C C O H
H
Acetic acid
H H
H C C O H
H
H Ethyl alcohol
H H
H H
H C C O C C
H
O
H
H H
“ether”
C OH
aspirin
O
C CH3
O
H
Introduction
 Organic compounds are commonly classified and
named based on the type of functional group
present.
 An atom or group of atoms that influences
the way the molecule functions, reacts or
behaves.
 The center of reactivity in an organic
compound
Functional Groups
 On your exam, you will be responsible for
recognizing and naming the various common
functional groups that are found in organic
compounds:
 Use Table 25.4 and the following slides to
help you study
Functional Groups
Class of Compound
Functional Group
Alkane
None
Cycloalkane
None
Alkyl halide
C
X
Alkene
C
C
Alkyne
C
C
Alcohol
C
OH
Ether
C
O
C
Functional Groups
Class of Compound
Aldehyde
Ketone
Carboxylic Acid
Ester
Functional Group
O
C
C
H
O
C
C
O
C
O
OH
C
O
C
Functional Groups
Class of Compound
Amine
Amide
Nitrile
Aromatic ring
Functional Group
C
N
O
C
N
C
R
R'
R
R'
N
Alkanes
 Contain C-C single bonds
 no functional group
 Tetrahedral electron domain
geometry
H
H
H
C C
H

sp3
H
H
H
C H
HH
hybridized
carbonsH H H
H
C C
H
H C C C H
H H H
H
H
H
C 3C
CH
CH
CH
2
3
H
H
H
H H H
H H H
H HCH CH
H C C C HC H
H C HC C H
H H H
H H
H H H
CH3CH2CH3
CH
CH
CH
CH
CH
CH
3
2
3
3
2
3
CC
C
H around single bonds
 Free rotation
H
H
H
H C C H
H
H
propane
Cycloalkanes
 Contain C – C with at least 3 of
the carbons arranged in a cyclic
(ring) structure
 No functional group
 Tetrahedral
 sp3 hybrid orbitals
CH2CH2CHCH2CH3
H
H
H
H
c
c
c c
H
H
H
c
H
H
H
Alkyl
Halides
H
H
H
CH2=CHCH3
H
H
H H
H
C
H
H C C C H
 Contain C-halogen bondH
H
H
HC
 F, Cl, Br, or I
H
CH2=CHCH3
CH2=CHCH3
C
C
H
C H
H H H H
C
C
H H H H
C C C HH C C C C H
H Br H H
H Br H H
H C
H
H
H CH C HC
C C
H
H
C H
H Br H H
CH3CH(Br)CH2CH3
CH3CH(Br)CH2CH3 CH3CH(Br)CH2CH3
Br
Br
Br
Alkenes
H
 Contain C=C (carbon-carbon
HH
H
double bonds)
 1 sigma bond & 1 pi bond
H
H
 sp2 hybridized carbons
C
C
H
CC CC
HH
H
CH
H 3
C
CH
3
H
H
CH2=CHCH3
 Trigonal planar geometry
Which atoms must
be coplanar in an
alkene?
C
H
CH2=CHCH3
C
H
H
C H
H
CH2=CHCH3
1-propene
Alkenes
 The C=C present in an alkene is composed of 1
sigma (s) bond and 1 pi (p) bond.
H
H
H
C C
ethylene
H
 Double bonds are rigid and cannot rotate
freely.
 Rotation would cause loss of overlap of the p
orbitals, destroying the p bond.
Alkynes
C
C
H C
C
CHH3
H
H
 Contain C
CH
triple bondsH
C
 1 sigma bond
H
 2 pi bonds
 Linear electron domain
C3
CH2=CHCH
H
H
geometry
C
H
C C
H
H
C H
H C C C
H
H
H
CH2=CHCH3
H
C
C
 sp hybridized carbons
H
H
H
H
C
C
C
C
H C
H C
C
C H
HC
CH3
H atoms must
Which
H
co-linear
in an
C CbeH
H
HC
alkyne?
C
H
C
H
C
H
C
Ph
H
Aromatic Ring
H
H
H
 Planar ring system with
alternating single and double
bonds
 does not react like an
alkene
CH CHCH
3
 Trigonal planar
H
C
CC
C
C
H
CCH3CHCH3
CC
H
H
H
C benzene
C
C
HC
H
C
C
H
C
C
C
Ph
H
C
C
H
C
C H
C
C
H
H
3
H
CH3CHCH3 C
CH3CHCH3
C
C
Ph
 sp2 hybridized carbons
C
 Benzene ring is a very common Ph
aromatic ring.
CH
C
C
C
C
C
C
C
H
C
H
C
H Ph
C
C H
C
C
H
N
H
..
N
pyridine
H
H
C
C
Functional Groups
 Alkanes are often called saturated
hydrocarbons
 Organic compounds composed of carbon and
hydrogen that contain the largest possible
number of hydrogen atoms per carbon atom.
 Alkenes, alkynes, and aromatic hydrocarbons
are called unsaturated hydrocarbons
 Organic compounds composed of carbon and
hydrogen that contain less hydrogen than an
alkane having the same number of carbon
atoms
Alcohols
CH3CH(OH)CH2CH(CH3)2
CH3CH(OH)CH2CH(CH
H
 Contain C-O-H bond
 hydroxyl group
H
 Alcohols form hydrogen
H
bonds.
H
O
C
C
H
H
C
H
H
H
H
C
C
C
H
H
H
C
C
H
OH H
CH CC
H
H
HH
H
H CH(CH
C H)
OH
CH CH(OH)CH
H
 How does hydrogen bonding
H
3
affect boiling point???
 Amphoteric
H
2
H
H
OH
H
O
H
H
H
C
C
C
C
C
3 2
H
Ethers
H
CH3CH(OH)CH2CH(CH3)2
O
 Contain
bond
H C C C-O-C
H
H
H
H
C
O
C
H
H
H
H
C
C
H H
CH3CH2OCH2CH
O C C H
(CH
CH
)O
 tetrahedral e.d. geometry
H
3
2 2
H
H
H
H
H
H H CH(CH ) H
CH3CH(OH)CH
2
3 2)
CH3CH(OH)CH
CH(CH
2
3 2
CH3CHO
H C C O C C H
O
HH
HH
CH2OCH2CH3
3
H CH
H
H
H
CH
CH2OCH2CH3
H
H
3
H
H
C
H
 bent
C
HH
H
O
H
C
C
H
HH
H
H
H
C C H
molecular
C OOHC C H
H C geo.
H H
H H
H H
H H
H
C
C
O
OH
(CH3CH2)2O
(CH3CH2)2O
O
Amines
 Contain C-N-R
H H
H C
H
H
HH H HH H H
H H H H H
H
H
H
H
C C C H CHC NHC CC HH
C C
H
H
H CC C C C C C CC CN NC C
H
H
H H
R’
 R and R’ can be H or C
H
H H
HH HH H
HH H H H H H HH HH HH H
H
CH
CH2CH2CH2CH
CH3CH2CH2CH2CH
NHCH
2 3
3
CH
CH
CH
NHCH
CH
CH
CHCH
CHCH
CH
NHCH
22
2
3
3 3 2 2 2 2 2
3
 Primary and secondary
amines form hydrogen
bonds.
 Common organic bases
 lone pair of e- on N
CH3NH2
o
1
primary
H
HH
N
NN
CH3NHCH3
o
2
secondary
H
N
(CH3)3N
o
3
tertiary
Aldehydes
H HO O
O
 Contain
C - H (-CHO)
H
H
 Carbonyl (C=O)
 always on the 1st or last carbon
in a chain
C
C
H
H
H H
O
O
H
H
C
H
CH CHO
CHCH
CHO
CHO
3
3
CH3CHO O O
 trigonal planar geometry
H O
 sp2 hybrid orbitals
H
H HC C C C H
H O
H H
C C H
C
H
H
Ketones
H
 Contain C-C-C
 Carbonyl attached to middle
of chain
CH3C(O)CH3
H e.d.
O H geo.
 Trigonal planar
C
O
C
C
H
O
H
H
C
H
 sp2 hybridized C
CH3CHO
C
H
H
H
CH3CHO
H
CH3C(O)CH3
C H
H
H
C
H O H
C
C
H
O
C
H
O
C
H
H
HH
H 3C(O)CH3
CH
CH
H 3CHO C
C
O O H
HH
H
H
O
H
H
C
H H C C CHH H
C H
C
H
C
C
H
H H
H
H
CH3CHO
N
N
Carboxylic Acids
H
CH3NH
NHCH3 (CH
)3NH 3)3N
CH2 3NHCH
3 CH3NHCH
3 (CH
2
3
O
H
H
H O
C
C
C
o
o
o
o
H
 Contain carboxyl
group
O
O H
H
1
2
3
1
2
3 H H H
H C C C O H
o
-CO2-CO
H 2H
o
O
C HC C
O C
H C O H
CH3CH2CO2H
H
H
-COOH
-COOH
H H
H H
H
 Form hydrogen bonds
 trigonal planar
 sp2 hybridized carbon
C
CH CHCH
COCH
H CO H
2
2
CH3CH23CO2H
3
2
2
O
OH
OH
H
HO
C
H
HH
C
O
C
O
OH
OH
H
H
C
C
Esters
H
C
OH
O
 Contain
-CO2R where R
OOH
HH
HH HH
H
O
H
H
H H
H H O
CO
HH
C C CC CCC OOH CC
C
C
C
H
H C C C O C C H
H H HH
HH
H
H
H
H group
= alkyl
HH HH
H
H
CC H
H
H
H
CHCH
CHCO
COCH
CHCH
CH3
CH3CH2COCH
CH
3CH
2
2
2
3
2
2
2
3
2
2
3
CH3CH2CO2CH
CH
2
3
 trigonal planar
 sp2 hybridized
O
O
H
H
H
H
H
H
H
O
HH
H
H
O
H
H
H
C H
H
O
C
H
H
C
O
C
C HOO C C
CH C
H
H
C
C
C
H
C
C
H
H
C
C
C C
C
C
OH H H H
H
H
HH
HHHO
H OO H
H
H
-CO2R where R = alkyl group
-CORR=where
R = alkyl group
-CO R where
alkyl group
Amides
H
 Contain
H
H O
 where R and R’H = CH or
C CC
H
H
H
H
H
H
HH
H
C
H
C
C
O
H H
H
H
H
CHCH
CH2CONHCH
CONHCH2CH
CH
CH
33
2
2 3 3
CH3CH2CONHCH2CH3
hybridized
H O
N C C H
H HHC CH CC CC N
C C H
H HH HH
N C HHC HHH
H
 C=O is trigonal planar &
sp2
H O
O
HH
H
H
NH
H
H H
C H
O
C
H
H
C
H H C C C OO C H H
C
C
CH
O
HH
H
C
C
HH
H
H
H
O
HH
-CO2R where R = alkyl group
-CO2R where R = alkyl group
H O H
H H
C H
O
C
H
C
C
Nitriles
C
C C N C C H
H
O
HH
H
H
H H H
 Contain
H
O
O
O
Linear 2CH3
CH2
CONHCH
H
3
CH3CNH2
CH3CNHCH3 CH3CN(CH3)2
N
 sp hybridized C
o
o
o
1
2
3
H
O
HH
H
C H
O
C
C H CC C N
N
CH3CN
H
O
HHH
O
O
H
H
CH3
H
Functional Groups
Example: Identify the functional groups present in the
following compounds.
OH
I
I
HO
O
I
I
thyroxine
NH2
CH2CHCOOH
O
testosterone
NH
Functional Groups
HO2C
Identify the functional groups in the N
Example:
following compounds.
H
NH2
O
C
HO2C
N
N
H
H
O
Lisinopril
C
O
OH
OH
OCH3
Vanillin
N
O
C
O
Depicting Structures of Organic
Compounds
 Organic compounds can be depicted using a
variety of formulas:







Empirical formula
Molecular formula
Lewis structure
Full structural formula
Three dimensional drawings
Condensed structural formula
Line angle drawings
Depicting Structures of Organic
Compounds
 Ethyl acetate is an organic molecule with:
 empirical formula = C2H4O
 molecular formula = C4H8O2
Depicting Structures of Organic
Compounds
 Ethyl acetate is an organic
molecule with:
 Lewis structure:
. ..
.
H O
 depicts all covalent bonds using H
a straight line and shows all
nonbonding pairs of electrons
C
H
. .
 Full structural formula:
 a Lewis structure without the
nonbonding electrons
C
..
O
..
H
H
C
C
H
H
H
..
..
H
O
C
C
H
H
O
H
H
C
C
H
H
H
Depicting Structures of Organic
Compounds
.
..
 Ethyl acetate is .an organic
..
molecule with:
 3-d drawing:H
. .
H
H O
O
H
O
H
HH
C..
C HO C C CH H
.. H
C
H
C
C H OH
H
H H H
H
 Condensed
C C H formula
H C C Ostructural
H
H H
CH3CO2CH2CH3
 Line angle drawing
CH3CO2CH2CH3
O
..
O
Alkanes
Some of the simplest alkanes:
Condensed
Formula
CH4
Name
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
2-methylbutane
CH3
CH3CCH3
CH3
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
 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
CH3 -2 CH - CH3
3 CH2
- CH2 - CH2 - CH3
4
5
6
Base name:
hexane
Alkanes
 Alkane Nomenclature:
 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
A substituent
CH3 -2 CH - CH3
3 CH2
- CH2 - CH2 - CH3
4
5
6
Alkanes
 Alkane Nomenclature:
 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
 Alkane Nomenclature:
 Common alkyl groups (substituents):
CH3
CH3CH2
CH3CH2CH2
CH3CH2CH2CH2
1
methyl
ethyl
propyl
butyl
Know
these!
CH3 -2 CH - CH3
3 CH2
- CH2 - CH2 - CH3
4
5
6
2-methylhexane
Alkanes
 Alkane Nomenclature:
 Halogen atoms are another common class of
substituents.
 Name halogen substituents as “halo”:
 Cl
chloro
 Br
bromo
I
iodo
F
fluoro
Alkanes
 Alkane Nomenclature:
 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
Know these.
 Tetra = four
 Penta = five
Alkanes
Example: Name the following compounds:
CH3CH2CHCH2CH3
CH3
CH2CH2CH3
CH3CHCHCH3
CH3
Alkanes
Example: Name the following compounds:
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
 Alkene Nomenclature
 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
 Alkene Nomenclature
 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
 Alkene Nomenclature
 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
C=C
H
H
C=C
H
cis-2-butene
H
CH3
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
CH3CH2
CH3CHCH2
CH3
H
H
C = C
H
CH2CH3
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
Example: Name the following compounds:
CH3CH2C
CCHCH3
CH2CH3
ClCH2CH2C
CH
Alkynes
Example: Draw the following alkynes.
4-chloro-2-pentyne
3-propyl-1-hexyne