Chemistry Lesson 8 Organic Chemistry

Chemistry Politecnico di Torino A.A.
2018-2019
Organic chemistry & polymers

Federico Carosio
Department of Applied Science and Technology
Tel.: +39 0131 229303

E-mail: federico.carosio@polito.it
Chemistry Politecnico di Torino A.A.2018-2019
Overview
Carbon Bonding
 mainly forms covalent bonds
 C is most stable when it has 4 single covalent bonds, but does
form double and triple bonds
 C=C and C≡C are more reactive than C−C
 C with 4 single bonds is tetrahedral,
 2 singles and 1 double is trigonal planar
 2 doubles or 1 triple and 1 single is linear
Overview
 Carbon uses sp3, sp2, and sp hybridization in forming the four

bonds per carbon atom common to almost all carbon compounds.
 With sp hybridization, there are two (2) p bonds and 2 s bonds.
 With sp2 hybridization there is one (1) p bond and 3 s bonds.
FUNCTIONAL GROUPS
1. Alkane
2. Alkene Organic chemistry is the study of
3. Alkyne compounds containing carbon.
The goal of studying Organic
4. Alkyl halide chemistry is the making of
5. Aromatic carbon-carbon bonds, C-X, C-O, C-N,
6. Alcohol and C-S bonds to make new molecules
7. Aldehyde
8. Ketone
9. Carboxylic Acid
10. Ester Inorganic molecules like CO, and
11. Amine CO3-2 are not considered organic
12. Amide molecules.
Hydrocarbons
 hydrocarbons contain only C and H
 aliphatic or aromatic
 insoluble in water
 no polar bonds to attract water molecules
 aliphatic hydrocarbons
 saturated or unsaturated aliphatics
 saturated = alkanes, unsaturated = alkenes or alkynes
 may be chains or rings (ciclo-)

 chains may be straight or branched
 aromatic hydrocarbons
Uses of Hydrocarbons
Number of
State Major Uses
C atoms
heating and
1-4 gas
cooking fuel
liquids,
liquids, solvents,
solvents,
5-7
5-7 (low
(low boiling)
boiling) gasoline
gasoline
6-18
6-18 liquids
liquids gasoline
gasoline
jet
jet fuel;
fuel; camp
camp
12-24
12-24 liquids
liquids stove
stove fuel
fuel
diesel fuel,
liquids,
18-50 lubricants,
(high boiling)
heating oil
petroleum jelly,
50+ solids
paraffin wax
Saturated
Hydrocarbons
 a saturated hydrocarbon has all C-C single bonds
 it is saturated with hydrogens
 saturated aliphatic hydrocarbons are called alkanes
 chain alkanes have the general formula CnH2n+2
Unsaturated Hydrocarbons
 unsaturated hydrocarbons have one of more C=C double bonds
or CC triple bonds
 unsaturated aliphatic hydrocarbons that contain C=C are called
alkenes
 the general formula of a monounsaturated chain alkene is CnH2n
 remove 2 more H for each additional unsaturation
 unsaturated aliphatic hydrocarbons that contain CC are called
alkynes
 the general formula of a monounsaturated chain alkyne is CnH2n-2
 remove 4 more H for each additional unsaturation
Unsaturated Hydrocarbons
CH3 H
H C
C CH3 HC CH2
C CH3
H3C C H3C C H2C CH2
H
C
CH3 H2
H2 H2
C C C C H2
H2C C C
H3C C C CH3 H2
H2C CH2
CH2 H2C
H2
H2C C CH2
C C
H2 H2
Aromatic
Hydrocarbons
 contain benzene ring structure
 even though they are often drawn with C=C, they do
not behave like alkenes
Hydrocarbons
Family
CH3 H
H C
C CH3 HC CH2
C CH3
H3C C H3C C H2C CH2
H
C
CH3 H2
alkenes
alkanes
H2 H2
C C C C H2
H2C C C
H3C C C CH3 H2
H2C CH2
CH2 H2C
H2
H2C C CH2
alkynes C C aromatic
H2 H2
Formulas
 molecular formulas just tell you what kinds

of atoms are in the molecule, but they don’t
tell you how they are attached
 structural formulas show you the attachment
pattern in the molecule
 models not only show you the attachment
pattern, but give you an idea about the shape
of the molecule
Condensed
Structural Formulas
 attached atoms listed in order
 central atom with attached atoms
 follow normal bonding patterns
 use to determine position of multiple bonds
 () used to indicate more than 1 identical group attached
to same previous central atom
 unless () group listed first in which case attached to next
central atom
Line-Angle
Formulas
 each angle, and beginning and end represent a C atom
 H omitted on C
 included on functional groups
 multiple bonds indicated
 double line is double bond, triple line is triple bond
Formulas
Alkanes
 aka paraffins
 Aliphatic: C hybrid sp3-σ
 general formula CnH2n+2 for chains
 very unreactive
 come in chains or/and rings
(cycloalkanes)
 CH3 groups at ends of chains, CH2
groups in the middle
 chains may be straight or branched
 saturated
 branched or unbranched
Alkanes
Name Lewis Formula Boiling
Structure Point
H
Methane H C H
CH4 -162°C
H
H H
Ethane H C C H
CH3CH3 -89°C
H H
H H H
Propane H C C C H
CH3CH2CH3 -42°C
H H H
H H H H
Butane H C C C C H CH3CH2CH2CH3 0°C
H H H H
H H H H H
Pentane H C C C C C H
CH3CH2CH2CH2CH3 36°C
H H H H H
H H H H H H
Hexane H C C C C C C H CH3CH2CH2CH2CH2CH3 69°C
H H H H H H
Naming: general rules
 each name consists of 3 parts
 prefix
 indicates position, number, and
type of branches
 indicates position, number, and
type of each functional group
 root
 indicates the length of the longest
carbon chain or ring (key point in
naming rules!)
 suffix
 indicates the type of hydrocarbon
 ane, ene, yne
 certain functional groups

Naming Alkanes
More Alkyl Groups

1) Find the longest continuous carbon chain

 The names of branched-chain hydrocarbons and hydrocarbon
derivatives are based on the name of the longest continuous carbon
chain in the molecule (which might not be shown in a horizontal line)
2) Identify and count substituents.
 Name a hydrocarbon side chain as a substituent by changing the ending
-ane to -yl
3) Number the backbone carbon atoms to give the lowest

numbers to the substituents.
 To indicate the position of a branch or substituent, the carbon atoms in
the longest chain are numbered consecutively from one end to the
other, starting at the end that will give the lower number(s) to the
substituent(s).
4) Indicate how many of each substituent are in the molecule by
the appropriate prefix.
 The prefixes di-, tri-, tetra-, penta-, hexa-, and so on, indicate how
many of each substituent are in the molecule. Numbers set off by
hyphens specify to which carbon atoms the groups are attached.
5) List the substituents in alphabetical order (disregarding the
Greek prefi xes) and attach them to the root name.
 When numbering substituents in equivalent positions, the one listed
first is assigned the lower number, as in 1-ethyl-2-methylcyclopentane
(not 2-ethyl-1-methylcyclopentane).
Naming Alkanes
1) Find the longest continuous carbon chain
 The names of branched-chain hydrocarbons and hydrocarbon
derivatives are based on the name of the longest continuous carbon
chain in the molecule (which might not be shown in a horizontal line)
10 C atoms
10 C atoms
Naming Alkanes
2) Identify and count substituents.
 Name a hydrocarbon side chain as a substituent by changing
the ending -ane to -yl
methyl
methyl
propyl
propyl
Naming Alkanes
3) Number the backbone carbon atoms to give the lowest
numbers to the substituents.
 To indicate the position of a branch or substituent, the carbon atoms in
the longest chain are numbered consecutively from one end to the
other, starting at the end that will give the lower number(s) to the
substituent(s).
10
9
9 8 7 6 5 4 3 2 1
8
1 2 3 5 6
10
4 7
Naming Alkanes
4) Indicate how many of each substituent are in the molecule by
the appropriate prefix.
 The prefi xes di-, tri-, tetra-, penta-, hexa-, and so on, indicate how many
of each substituent are in the molecule. Numbers set off by hyphens
specify to which carbon atoms the groups are attached.
di-methyl
di-methyl
propyl
di-propyl
Naming Alkanes
5) List the substituents in alphabetical order (disregarding the
Greek prefi xes) and attach them to the root name.
 When numbering substituents in equivalent positions, the one listed
first is assigned the lower number, as in 1-ethyl-2-methylcyclopentane
(not 2-ethyl-1-methylcyclopentane).
4,4-dimethyl- 5-propyl decane
4,5-dimethyl- 5,6-dipropyl decane

Example – Name the alkane

CH3CHCH2CHCH3
CH3 CH3
1) find the longest continuous C chain and use it to
determine the base name
CH3CHCH2CHCH3
CH3 CH3
since the longest chain has 5 C
the base name is pentane

CH3CHCH2CHCH3
CH3 CH3
2) identify the substituent branches
CH3CHCH2CHCH3
CH3 CH3
there are 2 substituents
both are 1 C chains, called methyl

3) number the chain from the end closest to a
substituent branch
 if first substituents equidistant from end, go to next
substituent in
then assign numbers to each substituent based
on the number of the main chain C it’s attached to
1 2 3 4 5
CH3CHCH2CHCH3
both substituents are
equidistant from the end
CH3 CH3
2 4

4) write the name in the following order
1) substituent number of first alphabetical substituent
followed by dash
2) substituent name of first alphabetical substituent
followed by dash
 if it’s the last substituent listed, no dash
 use prefixes to indicate multiple identical substituents
3) repeat for other substituents alphabetically
4) name of main chain
CH3CHCH2CHCH3 2,4 – dimethylpentane
CH3 CH3
2 4
Drawing Structural
Formulas
 draw and number the 4-ethyl-2-methylhexane
base chain carbon
skeleton C C C C C C
1 2 3 4 5 6
 add the carbon
skeletons of each C C C C C C
substituent on the C C C
appropriate main chain
C CH3 CH CH2 CH CH2 CH3
 add in required H’s CH3 H2C CH3

Examples of Naming Alkanes

H H H H H
2-methylpentane H C C C C C H
H CH3 H H H
H CH3 H H H H
3-isopropyl-2,2-dimethylhexane H C C C C C C H
H CH3 CH H H H
CH3 CH3
Practice – Name the Following

CH3
CH3 CHCHCH2 CH3 3-ethyl-2-methylpentane
CH2 CH3
Practice – Draw the structural formula of 4-

isopropyl-2-methylheptane
CH3 CH CH2 CH CH2 CH2 CH3
CH3 HC CH3
CH3
Cycloalcanes
•hydrocarbon
•formula CnH2n
•C hybrid sp3
•Single bonds
Cyclopropane cyclobutane cyclopenthane cyclohexane

The Shapes of Cycloalkanes:
Planar or Nonplanar?
CHAIR (more stable)
 All of the
bonds are
staggered and the
bond angles at
carbon are close to
tetrahedral.
180 pm
BOAT
 All of the bond angles
are close to tetrahedral
but close contact
between flagpole
hydrogens
causes van der Waals
strain in boat.
Naming
Cycloalcanes
• Substituted cycloalkanes are named in a fashion very similar to
that used for naming branched alkanes.
• The chief difference in the rules and procedures occurs in the
numbering system.
• Since all the carbons of a ring are equivalent (a ring has no
ends like a chain does), the numbering starts at a substituted
ring atom.
CH2 CH3
1
6 2 1-ethyl-3-methyl cyclohexane
5 3
4
CH3
Cycloalkane Molecular Basic
Formula Structure
Cyclopropane C3H6
1. For a
monosubstituted
Cyclobutane C4H8
cycloalkane the ring
supplies the root
Cyclopentane C5H10
name (table) and the
substituent group is
Cyclohexane C6H12
named as usual. A
location number is
Cycloheptane C7H14
unnecessary.
Cyclooctane C8H16
Cyclononane C9H18
Cyclodecane C10H20
Naming
Cycloalcanes
2. If the substituent is an alkyl chain
large and/or complex, the ring may be
named as a substituent group on an
alkane.
3. If several substituents are present
on the ring, they are listed in
alphabetical order. Location numbers
are assigned to the substituents so that
one of them is at carbon #1 and the other
locations have the lowest possible
numbers, counting in either a clockwise
or counter-clockwise direction.
4. The name is assembled, listing
groups in alphabetical order and giving
each group (if there are two or more) a
location number. The prefixes di, tri,
tetra etc., are not considered when
alphabetizing.
Seven-carbon ring bearing a

C4H9 substituent group. Earlier this
substituent was identified as the tert-
butyl group, so a name based on the
cycloheptane root is easily written.
The best approach is to

name this compound as a
disubstituted pentane. The
four-membered ring
substituent is called a
cyclobutyl group.
• Three substituents on the six-membered ring and two are on the same carbon.
The disubstituted carbon becomes #1 because the total locator numbers are
thereby kept to a minimum.
• The ethyl substituent is then located on carbon #3 (counter-clockwise
numbering), not #5 (clockwise numbering).
• Alphabetical listing of the substituents then leads to the name "3-ethyl-1,1-
dimethylcyclohexane", being careful to assign a locator number to each
substituent.
• Note that if only one methyl substituent was present, the alphabetical citation
rule would assign the ethyl group to carbon #1 and the methyl to #3.
Properties of
Hydrocarbon molecules are best regarded as Alkanes
nonpolar.
• The dominant interaction between alkane
molecules is the London force.
• Alkanes with long, unbranched chains tend to
have higher melting points, boiling points,
and enthalpies of vaporization than those of
their branched isomers.
• The alkanes were once called the paraffins, from Latin words
meaning “little affinity.” As this name suggests, they are not very
reactive.
They are unaffected

• by concentrated sulfuric acid,
• by boiling nitric acid,
• by strong oxidizing agents such as
potassium permanganate,
• by boiling aqueous sodium
hydroxide.
Alkenes
 also known as olefins
 aliphatic, unsaturated (more later) ethene = ethylene
 C=C double bonds
 formula for one double bond = CnH2n H H
 subtract 2 H from alkane for each double bond C C
 trigonal shape around C H H
 flat
 much more reactive than alkanes
 polyunsaturated = many double bonds
propene H H
C C
H CH3
Alkynes
 also known as acetylenes
ethyne = acetylene
 aliphatic, unsaturated
 CC triple bond H C C H
 formula for one triple bond = CnH2n-2
 subtract 4 H from alkane for each triple bond
 linear shape
 more reactive than alkenes
H C C CH3
propyne
Naming Alkenes and Alkynes

 Change suffix on main name (longest chain) from -ane to -ene for
base name of alkene, or to -yne for the base name of the alkyne
 The position of the multiple bond is given by the number of the
first (lower-numbered) carbon atom involved in the bond
 When numbering the chain: lowest numbers are given
preferentially to: 1) double bonds, 2) triplebonds, and 3)
groups named by prefixes
 If more than one multiple bond of the same type is present, the
number of these bonds is indicated by a Greek prefix (as before).
Name the Alkene

1) find the longest, continuous C chain that
contains the double bond and use it to
H2C CH3
H3C CH C CH CH3
H2C CH3
since the longest chain with the double bond has 6 C

the base name is hexene
Name the Alkene

H2C CH3
H3C CH C CH CH3
H2C CH3

one is a 1 C chain, called methyl
the other one is a 2 C chain, called ethyl
Name the Alkene

3) number the chain from the end closest to the
double bond
3
H2C CH3
4
H3C CH C CH CH3
4 3 2 1
H2C CH3
5 6
Name the Alkene

1) substituent number of first alphabetical substituent –
substituent name of first alphabetical substituent –
2) repeat for other substituents
3) number of first C in double bond – name of main
chain
3
H2C CH3 3–ethyl– 4–methyl–2–hexene
4
H3C CH C CH CH3
4 3 2 1
H2C CH3
5 6
Name the Alkyne

1) find the longest, continuous C chain that
contains the triple bond and use it to
CH3 CH CH2 CH C C CH3
CH3 HC CH3
CH3
since the longest chain with the triple bond has 7 C
the base name is heptyne
Name the Alkyne


CH3 HC CH3
CH3
one is a 1 C chain, called methyl
the other one is called isopropyl
Name the Alkyne

3) number the chain from the end closest to the
triple bond

7 6 5 4 3 2 1
6 CH3 HC CH3
4
CH3
Name the Alkyne

1) substituent number of first alphabetical substituent –
substituent name of first alphabetical substituent –
2) repeat for other substituents
3) number of first C in double bond – name of main
chain

7 6 5 4 3 2 1
6 CH3 HC CH3
4
CH3 4–isopropyl–6–methyl–2–heptyne

CH3
H3C 3C C4 CH2 CH3
5 6 3,4-dimethyl-3-hexene
H2C CH3
2 1
CH3
H3C C C CH 3,3-dimethyl-1-pentyne
3 2 1
CH2CH3
4 5
Examples of Naming Alkenes

H H H
2-methyl-1-pentene H C C C C C H
H CH3 H H H
H CH3 H H
3-isopropyl-2,2-dimethyl-3-hexene H C C C C C C H
H CH3 CH H H H
CH3 CH3
Examples of Naming Alkynes

H H H
3-methyl-1-pentyne H C C C C C H
CH3 H H
H CH3 H H
4-isopropyl-5,5-dimethyl-2-hexyne H C C C C C C H
H CH3 CH H
CH3 CH3
Isomerism
Isomers = different molecules with the same molecular
formula
 Structural Isomers = different

pattern of atom attachment
 Constitutional Isomers
 Stereoisomers = same
atom attachments,
different spatial
orientation
H H H H H H H
H Structural
C C C C H Isomers of
H CC4CH10C H
HH HHBPH= 0°C
HButane, H H HH BP H
HIsobutane, = -12°C
H C H
C C C H H C C C H HH H
H H H H
H C C HC H
H H CH C C C H
H H H
H H
H H H H H C H H C H
H H
Nr. isomers
Possible Structural
Isomers
Rotation about a bond is not isomerism

Write the structural formula and carbon skeleton

formula for C6H14
start by C C C C C C
connecting CC CC C
C CC C
the carbons
C C
C C
C C
C C
in a line
C
determine
the C
skeleton of
the other
isomers

formula for C6H14
fill in the H H H H H H H
H C
C C C C C C H
to give each
H H H H H H
C 4 bonds
H H H H H H H H H H
H C C C C H
C C H C C C C H
C C
H C H H H H H C H H
H C H H C H
H H H
H C H H H H H
H C H H
H C CC C C CC C H
H CC C
C C C
C H
H C C H
H C H H
H C H H C H
H C H
H H
H

formula for C6H14
convert each H H H H H H
H C C C C C C H
to a carbon
H H H H H H
skeleton
formula – H H H H H H H H H H
H C C C C C H H C C C C C H
each bend
H H H H H H H H
and the ends H C H H C H
represent C H H
H
atoms H C H H H H H
H H H H C C C C H
H C C C C H
H H
H H H
H C H H C H
H C H
H H
H
Stereoisomers
 stereoisomers are different molecules whose atoms are
connected in the same order, but have a different spatial
direction
 optical isomers are molecules that

are nonsuperimposable mirror images
of each other
 geometric isomers are

stereoisomers that are not optical
isomers
Nonsuperimposable
Mirror Images
mirror image cannot be rotated so all its atoms align

with the same atoms of the original molecule
Chirality
 any molecule with a nonsuperimposable mirror image is said
to be chiral
 any carbon with 4 different substituents will be a chiral
center
 a pair of nonsuperimposable mirror images are called a pair
of enantiomers
Optical Isomers of 3-methylhexane

Define whether the following molecules

are optical isomers or not; if yes
identify the chiral center
Optical Activity
 a pair of enantiomers have all the same physical properties
except one – the direction they rotate the plane of plane
polarized light
 each will rotate the plane the same amount, but in opposite directions
 dextrorotatory = rotate to the right
 levorotatory = rotate to the left
 an equimolar mixture of the pair is called a racemic mixture

 rotations cancel, so no net rotation
Chemical Behavior
of Enantiomers
 a pair of enantiomers will have the same chemical reactivity
in a non-chiral environment
 but in a chiral environment they may exhibit different
behaviors
 enzyme selection of one enantiomer of a pair
Geometric Isomerism
 because the rotation around a double bond is highly restricted,
you will have different molecules if groups have different spatial
orientation about the double bond
 this is often called cis-trans isomerism
 when groups on the doubly bonded carbons are cis, they are on
the same side
 when groups on the doubly bonded carbons are trans, they are
on opposite sides
Free Rotation Around C─C
Blocked Rotation Around C=C

Cis-Trans
Isomerism
• Geometrical isomers of
organic molecules are
distinguished by the
prefixes cis- and trans-.
Reactions of
 all hydrocarbons undergo combustion
Hydrocarbons
 combustion is always exothermic
 about 90% of U.S. energy generated by combustion
2 CH3CH2CH2CH3(g) + 13 O2(g) → 8 CO2(g) + 10 H2O(g)
CH3CH=CHCH3(g) + 6 O2(g) → 4 CO2(g) + 4 H2O(g)
2 CH3CCCH3(g) + 11 O2(g) → 8 CO2(g) + 6 H2O(g)
Other Alkane
Reactions
 Substitution
 replace H with a halogen
atom
 initiated by addition of
energy in the form of heat or
ultraviolet light
 to start breaking bonds
 generally get multiple
products with multiple
substitutions
heat or
H H H Cl
UV light
H C C H + Cl Cl H C C H + H Cl
H H H H
Other Alkene and

Alkyne Reactions
 Addition reactions
 adding a molecule across the
multiple bond
 Hydrogenation = adding H2
 converts unsaturated molecule to
saturated
 alkene or alkyne + H2 → alkane
 Halogenation = adding X2
 Hydrohalogenation = adding HX
 HX is polar
 when adding a polar reagent to a double or triple bond, the
positive part attaches to the carbon with the most H’s
Aromatic
Hydrocarbons
 contain benzene ring structure
 even though they are often drawn with C=C, they do not
behave like alkenes
 the true structure of benzene is a resonance hybrid of two
structures
Naming Monosubstituted
Benzene Derivatives
 Name= (name of substituent)benzene
 halogen substituent = change ending to “o”
F CH2CH2CH3
fluorobenzene propylbenzene
• or name of a common derivative
CH3 NH2 OH HC CH2
toluene aniline phenol styrene

Naming Benzene as
a Substituent
 when the benzene ring is not the base name, it is called
a phenyl group
H2C CH CH2 CH CH2 CH3
4-phenyl-1-hexene
3-phenyl-pentane
1 methyl-3-phenyl-cyclohexane
Naming multi-substituted
Benzene Derivatives
 number the ring starting at attachment for first
substituent, then move toward second
 order substituents alphabetically
 use “di, tri,” etc. if substituents are the same
CH3
F 1
CH3 CH3
3 2
2 H3C CH3
1 Br 1,2-dimethylbenzene
H3C CH3
1-bromo-3-fluorobenzene
pentamethylbenzene
The position numbers must be determined so that they are as

small as possible.
Naming Disubstituted
Benzene Derivatives
 alternatively, use relative position prefix
 ortho- = 1,2; meta- = 1,3; para- = 1,4
Examples
CH3 CH3 CH3

Cl
Cl
Cl
2-chlorotoluene 3-chlorotoluene 4-chlorotoluene
ortho-chlorotoluene meta-chlorotoluene para-chlorotoluene
o-chlorotoluene m-chlorotoluene p-chlorotoluene

F Br
Br
Cl
1-chloro-4-fluorobenzene 1,3-dibromobenzene
or meta-dibromobenzene
or m-dibromobenzene
Other aromatic
compounds
Polycyclic Aromatic
Hydrocarbons
 contain multiple benzene rings fused together
 fusing = sharing a common bond
pyridine
furane thiophene
Reactions of Aromatic
Hydrocarbons
 most commonly, aromatic hydrocarbons undergo substitution
reactions – replacing H with another atom or group
Fuels
 Aliphatic hydrocarbons are obtained primarily from petroleum,
which is a mixture of aliphatic and aromatic hydrocarbons,
together with some organic compounds containing sulfur and
nitrogen
• Coal is another major source
of aromatic hydrocarbons.
Fuels
Fuels
https://www.youtube.com/watch?v=BaBMXgVBQKk
Fuels
 The quantity of gasoline that can be obtained from petroleum is
increased by:
 cracking (breaking down long hydrocarbon chains)
 alkylation (combining small molecules to make larger ones).
• Aromatization is the conversion of an alkane into an arene:

Fuels
 The quality of gasoline, which determines
how smoothly it burns, is measured by the
octane rating.
 The octane rating of gasoline is measured in
a test engine and is defined by comparison
with the mixture of
2,2,4-trimethylpentane (iso-octane) and heptane
rating 100 rating 0

 In isomerization, straight-chain hydrocarbons (low rating) are converted into
their branched-chain isomers(high rating).
Functional Groups
 other organic compounds are hydrocarbons in which

functional groups have been substituted for hydrogens
 a functional group is a group of atoms that show a

characteristic influence on the properties of the molecule
 generally, the reactions that a compound will perform are determined
by what functional groups it has
 since the kind of hydrocarbon chain is irrelevant to the reactions, it
may be indicated by the general symbol R
CH3—OH
R group functional group
Nomenclature
103
Haloalkanes
 The haloalkanes (also called alkyl
halides) are alkanes in which at least one
hydrogen atom has been replaced by a
halogen atom.
 Although they have important uses,
many haloalkanes are highly toxic and a
threat to the environment.
 Naming:
 Treat the halogen atom as substituent using prefixes di-, tri-, tetra-
, penta-, hexa-… and C positioning
Br Cl Cl
CH3 CH2 CH CH3 CH3 CH2 CH2 CH CH2
2-bromo-butane 1,2-dichloro-pentane
Alcohols
 R-OH
 ethanol = CH3CH2OH
 grain alcohol = fermentation of sugars
 alcoholic beverages
 proof number = 2X percentage of alcohol
 isopropyl alcohol = (CH3)2CHOH
 2-propanol
 rubbing alcohol
 poisonous
 methanol = CH3OH
 wood alcohol = thermolysis of wood
 paint solvent
 poisonous
Naming Alcohols
 main chain contain OH, three way of naming:
1. Add the suffix -ol to the stem of the parent hydrocarbon (count
C atoms), as in methanol and ethanol (use diol with 2 OH).
When the location of the -OH group needs to be specified (to
avoid ambiguity), the number of the carbon atom to which it is
attached is given
OH CH3
1 2 3 4 5 6
CH3 CH2 CH C CH CH2
ethanol
CH2CH3
4-ethyl-4-methyl-5-hex-3-enol
Naming Alcohols
 main chain contain OH, three way of naming:
2. Name the parent hydrocarbon as a group and attach the name
alcohol,
3. Name the -OH group as a substituent, in which case the name
hydroxy is used (with common rules for substituent)
CH3 CH2 OH
CH3 CH2 CH CH3
Ethyl alcohol
2-butanol OH
2-hydroxy butane
OH Phenol: the molecule consists of a phenyl

group (−C6H5) bonded to a hydroxyl group
(−OH).
• Alcohols are divided into three classes

according to the number of organic
groups attached to the carbon atom
connected to the -OH group
Ethers
 An ether is an organic compound of
the form R– O – R
 ether = diethyl ether =
CH3CH2OCH2CH3
 anesthetic
 to name ethers, name each alkyl group
attached to the O, then add the word
ether to the end
Ethers are not very reactive. They are

more volatile than alcohols with
similar molar masses because their
molecules cannot form hydrogen
diethyl ether bonds with one another.
Carbonyl Group
C=O group is highly polar

many reactions involve addition across C=O,
with positive part attached to O
Aldehydes and Ketones

aldehydes
 contain the carbonyl group carbonyl
 aldehydes = at least 1 side H
 ketones = both sides R groups
 many aldehydes and ketones have
pleasant tastes and aromas
 some are pheromones ketone
 formaldehyde = H2C=O
 pungent gas
 formalin = a preservative
 wood smoke, carcinogenic
 acetone = CH3C(=O)CH3
 nail-polish remover
Naming Aldehydes and
Ketones
 Always count the C atom to determine the root of
the name
 Aldehydes are obtained by using the suffix -al.
Note: the carbon atom of the carbonyl group is
included in the count of carbon atoms when
determining the alkane from which the aldehyde is methanal
derived.
 Ketones are given the suffix -one. To avoid
ambiguity, a number is used to denote the carbon
atom that has become the carbonyl group. pentanal
propanone
3-ethyl-2-hexanone
Aldehyde Odors
and Flavors
O
 butanal = butter C CH2CH2CH3
H
O O
 vanillin = vanilla HO H
HO
 benzaldehyde = almonds
O
C
H
 cinnamaldehyde = cinnamon
O
H
C
C C H
H
113
Ketone Odors and
Flavors
 acetophenone = pistachio
O
C
H3C
 carvone = spearmint
H3C
CH2
O C
CH3
 ionone = raspberries
H3C CH3 O
H
C C C CH3
H
CH3
 muscone = musk
O CH3
Carboxylic Acids
O
 RCOOH CH2 C OH
 sour tasting O
HO C C OH
 weak acids
 citric acid CH2 C OH
O
 found in citrus fruit
 ethanoic acid = acetic acid
 vinegar O
 methanoic acid = formic acid CH3 C OH
 insect bites and stings
O
H C OH
Carboxylic
 made by the oxidation of aldehydes and Acids

alcohols
 OH on the end of the chain
 always on main chain
 has highest precedence
 C of group always C1
 position not indicated in name
 Always count the C atom to determine the

root of the name
 Name obtained by replacing the ending
with -oic acid. Note: the carbon atom of
the carboxylic group is included in the 3-methyl-
count of carbon atoms. eptanoic acid
 Other groups are treated as substituents
Naming Carboxylic
Acids
Esters
 R–COO–R
 sweet odor
 made by reacting carboxylic acid with an alcohol
(esterification)
O
C
OH
O C CH3
O
methyl butanoate aspirin
 Change the -anol of the alcohol to -yl and the -oic acid of the
parent acid to -oate.
 precedence over carbonyls, but not carboxylic acid
 number from end with ester group
 Change the -anol of the alcohol to -yl and the -oic acid of the
parent acid to -oate.
 precedence over carbonyls, but not carboxylic acid
 number from end with ester group
+ +
methanol
ethanol
+ H2O + H2O
Condensation
Reactions
 a condensation reaction is any organic reaction driven by the
removal of a small molecule, like water
• esters are made by the condensation reaction between a carboxylic
acid and an alcohol
 the reaction is acid catalyzed
• acid anhydrides are made by the condensation reaction between

2 carboxylic acid molecules
 the reaction is driven by heat
O
+ O O O
+ HOH
R C OH HO C R' R C O C R'
Amines
 N containing organic molecules
H3C NH
 very bad smelling
 form when proteins decompose H3C CH2
 organic bases ethylmethylamine
H2NCH2CH2CH2CH2NH2 H2NCH2CH2CH2CH2CH2NH2
putrescine cadaverine
Amines
 Amines are named systematically by specifying the
groups attached to the nitrogen atom in alphabetical order
(disregarding prefixes), followed by the suffix -amine.
Amines with two amino groups are called diamines.
 The -NH2 group is called amino- when it is a substituent.
H
2-aminopropane
H3C N
CH3
Dimethylamine
CH3
H3C N NH2 CH2 (CH2)2 CH2 NH2
CH3 1, 4-butanediamine
Trimethylamine Or 1, 4-diaminobutane
Amines
• Amines are classified as primary,

secondary, or tertiary according to
the number of R groups on the
nitrogen atom
Amines
 many amines are biologically active

 dopamine – a neurotransmitter HO CH2CH2NH2
 epinephrine – an adrenal hormone
HO dopamine
 pyridoxine – vitamin B6
 alkaloids are plant products that are
alkaline and biologically active
 toxic N
 coniine from hemlock CH3
 cocaine from coca leaves N
nicotine
 nicotine from tobacco leaves
 mescaline from peyote cactus
 morphine from opium poppies
Amine Reactions
 weak bases
 react with strong acids to form ammonium salts
RNH2 + HCl → RNH3+Cl−
 react with carboxylic acids in a condensation reaction
to form amides
RCOOH + HNHR’  RCONHR’ + H2O
Aminoacids
 An amino acid is a carboxylic acid that contains an amino
group as well as a carboxyl group.
 Notice that an amino acid has both a basic group (-NH2)
and an acidic group (-COOH) in the same molecule.
Alanine and its

Fractional
composition in water
as a function of pH
Nomenclature suffix priority
When compounds contain more than one functional group, the priority
determines which groups are named with prefix or suffix forms.
The highest-precedence group takes the suffix, with all others taking the prefix form.
Macromolecules
 polymers are very large
molecules made by repeated
linking together of small
molecules
 monomers
 natural
 modified natural polymers
 synthetic
 plastics, elastomers (rubber),
fabrics, adhesives
 composites
 additives such as graphite, glass,
metallic flakes
The plastics tree
oil
Molecular Structure
of Polymers
 Linear
 High Density Polyethylene (HDPE), PVC, Nylon,
Cotton
 Branched
 Low Density
Polyethylene (LDPE)
 Cross-linked
 Rubber
 Network
 Kevlar, Epoxy
 Polymerization: the process of linking the monomer

units together
 two processes are addition polymerization and
condensation polymerization
Addition
Polymerization
 monomers add to the growing chain in such a manner
that all the atoms in the original monomer wind up in
the chain
 no other side products formed, no atoms eliminated
 first monomer must “open” to start reaction
 done with heat or addition of an initiator
 chain reaction
 each added unit ready to add another
initiator
etc.
Addition
Polymerization
H H
H H
initiator
C C H C C •
Cl H
Cl H
H H H H H H
H H
H C C• + C C H C C C C •
Cl H
Cl H Cl H Cl H
H H H H H H H H H H
H H
H C C C C• + C C H C C C C C C •
Cl H Cl H Cl H Cl H Cl H Cl H
Low-Density
Chain Length: 1000 - Polyethylene (LDPE)
2000
High-Density
Chain Length: 10,000 – Polyethylene (HDPE)
100,000
Ultra-high-molecular-
weight polyethylene
Chain Length: 2-6 million
(UHMWPE)
Joint
Replacement
Helmet
Gears
Condensation
Polymerization
 monomer units are joined by removing small molecules from
the combining units
 polyesters, polyamides lose water
 no initiator needed, chain reaction
 each monomer has two reactive ends, so chain can grow in two
directions
*Technically polyurethane is not a condensation polymer since

no molecules are lost, but the functional group does rearrange.
Polyethylentereftalate (PET)
Ester group
72°C: from glass to gum behaviou

  plastic bottles
If kept > 72°C for a long time:

crystallization, hardness and opacity 
oven vessels
Nylon
 polyamides
 good physical properties
 affected by moisture
 very good heat resistance
 excellent chemical resistance
 excellent wear resistance
 nylon 6,6 made by condensing
1,6–hexandiamine, H2N–(CH2)6–NH2, with
hexandioic acid, HOOC–(CH2)4–COOH

Chemistry Lesson 8 Organic Chemistry

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Chemistry Lesson 8 Organic Chemistry

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Chemistry Politecnico di Torino A.A.

Organic chemistry & polymers

Department of Applied Science and Technology

Tel.: +39 0131 229303

 Carbon uses sp3, sp2, and sp hybridization in forming the four

 may be chains or rings (ciclo-)

 molecular formulas just tell you what kinds

 certain functional groups

More Alkyl Groups

1) Find the longest continuous carbon chain

3) Number the backbone carbon atoms to give the lowest

4,4-dimethyl- 5-propyl decane

4,5-dimethyl- 5,6-dipropyl decane

Example – Name the alkane

Example – Name the alkane

Example – Name the alkane

Example – Name the alkane

CH3CHCH2CHCH3 2,4 – dimethylpentane

 add in required H’s CH3 H2C CH3

Examples of Naming Alkanes

Practice – Name the Following

Practice – Draw the structural formula of 4-

Cyclopropane cyclobutane cyclopenthane cyclohexane

Seven-carbon ring bearing a

The best approach is to

They are unaffected

Naming Alkenes and Alkynes

Name the Alkene

since the longest chain with the double bond has 6 C

Name the Alkene

there are 2 substituents

Name the Alkene

Name the Alkene

Name the Alkyne

Name the Alkyne

CH3 CH CH2 CH C C CH3

Name the Alkyne

CH3 CH CH2 CH C C CH3

Name the Alkyne

CH3 CH CH2 CH C C CH3

Practice – Name the Following

Examples of Naming Alkenes

Examples of Naming Alkynes

 Structural Isomers = different

Rotation about a bond is not isomerism

Write the structural formula and carbon skeleton

Write the structural formula and carbon skeleton

Write the structural formula and carbon skeleton

 optical isomers are molecules that

 geometric isomers are

mirror image cannot be rotated so all its atoms align

Optical Isomers of 3-methylhexane

Define whether the following molecules

 dextrorotatory = rotate to the right

 levorotatory = rotate to the left

 an equimolar mixture of the pair is called a racemic mixture

Free Rotation Around C─C

Blocked Rotation Around C=C

Other Alkene and

• or name of a common derivative

CH3 NH2 OH HC CH2

toluene aniline phenol styrene

H2C CH CH2 CH CH2 CH3