Unit 17 Organic Chemistry

History Of Organic Chemistry

• Origin of Organic Chemistry, Lavoisier(1743-
1794) French, father of modern science. He
showed that nearly all substances of plant and
animal origin are composed: Carbon,
Hydrogen and Oxygen.
• Organic compounds are Animal and Plant
origin also consist of the same three
elements( C, H, O) but frequently contain
Nitrogen and some times Sulfur and
Phosphorus.
 Vital Force Theory
• Organic compounds can not be prepared in
the laboratory because of Vital Force(Life
force)
• Berzelius believes that some vital force(life
force) was necessary to produce Organic
compounds and an artificial preparation of
these was impossible due to the absence of
this vital force in the test tube.
• The mysterious of this force in the body of the
living organism was responsible for the
synthesis or organic compounds.
 Removed of vital force theory
• Karl Scheele(1742-1786).prepared Oxalic Acid
by reacting Sugar with Nitric Acid. This shows
Organic Compound could be made by
Laboratory.
• C6H12O6 + HNO3 → C2O4H2
Sugar( Glucose) Nitric Acid Oxalic Acid
Friedrich Wohler(German chemist)
The first step in the decline of the vital force
theory occurred in 1828, when Friederich
Wohler synthesized urea from inorganic
starting materials. Wohler was trying to make
ammonium cyanate (NH4OCN) from silver
cyanate (AgOCN) and ammonium chloride
(NH4Cl). What he expected is described by the
following equation.
• AgOCN(aq) + NH4Cl(aq) →AgCl(s) +NH4OCN(aq)
• The product he isolated from this reaction had none o
the properties of cyanate compounds. It was a white,
crystalline material that was identical to urea,
H2NCONH2, which could be isolated from urine.
• Neither Wohler nor his contemporaries
claimed that his results disproved the vital
force theory. But his results set in motion a
series of experiments that led to the synthesis
of a variety of organic compounds from
inorganic starting materials. This inevitably led
to the disappearance of "vital force" from the
list of theories that had any relevance to
chemistry.
Organic Chemistry definition

Modern definition: is the chemistry

of carbon and Hydrogen and their
derivatives.
 Definition and Classification
of Hydrocarbons

• Hydrocarbon : is only composed of carbon

and hydrogen .
 Classification

• Organic chemistry can be classified in to

different ways.
• 1- a) Saturated b) unsaturated
• 2- a) Cyclic b) Acyclic
• 3- a) Aliphatic b) Aromatic
 1- Saturated & unsaturated
Saturated: An organic compound in which the
carbon atom are joined by single bond.
Unsaturated: An organic compounds in which
some of the carbon atoms are joined by
double or triple.
 Cyclic & Acyclic
Aromatic & Aliphatic
• Cyclic: Are those containing ring form.
• Acyclic: Are those open chain mloecule.
• Aromatic: are those containing benzene ring.
• Aliphatic: Open chain hydrocarbon.
 Organic derivatives

• Most commonly Oxygen and Nitrogen . Some

times sulfur, phosphorus, and halogens
 Alakanes(paraffins)
• Alkanes(paraffins=Little affinity)
• Are open chain saturated hydrocarbon
containing C-C single bond, C-H bond.
• General formula: CnH2n+2
•
 Organic Compounds and Structures: An
Overview
• Hydrocarbons – the simplest organic
compounds.
• Simplest hydrocarbon is methane.

Slide 18 of 75 Prentice-Hall © 2002 General Chemistry: Chapter 27

• Number of Carbons Prefix Structure 1
Methane CH4
• 2 Ethane CH3CH3
• 3 Propane CH3CH2CH3
• 4 Butane CH3(CH2)2CH3
• 5 Pentane CH3(CH2)3CH3
• 6 Hexane CH3(CH2)4CH3
• 7 Heptane CH3(CH2)5CH3
• 8 Octane CH3(CH2)6CH3
• 9 Nonane CH3(CH2)7CH3
• 10 Decane CH3(CH2)8CH3
• 11 Undecane CH3(CH2)9CH3
• 12 Dodecane CH3(CH2)10CH3
• C13H28 n-Tridecane
• C14H30 n-Tetradecane
• C15H32 n-Pentadecane
• C16H34 n-Hexadecane; cetane
• C17H36 n-Heptadecane
• C18H38 n-Octadecane
• C19H40 n-Nonadecane
• C20H42 n-Icosane; eicosane
• C21H44 n-henicosane
• C22H46 n-Docosane
• C23H48 n-Tricosane
• C30H62 n-Triacontane
• C31H64 n-hentriacontane; untriacontane
• C32H66 n-Dotriacontane
• C40H82 n-Tetracontane
• C41H84 n-Hentetracontane, untriacontane
• C42H86 n-Dotetracontane
• C50H102 n-Pentacontane
• C60H122 n-Hexacontane
• C70H142 n-Heptacontane
• C80H162 n-Octacontane
• C90H182 n-Nonacontane
• C100H202 n-Hectane
 Ethane

Slide 26 of 75 Prentice-Hall © 2002 General Chemistry: Chapter 27

 Skeletal Isomerism

SlidePrentice
27 of 75 Hall © 2002 General Chemistry:
Prentice-Hall ©Chapter
2002 27 Slide 5 Chapter
General Chemistry: of 27
 Simplified Drawings of Organic Structures

Slide 28 of 75 Prentice-Hall © 2002 General Chemistry: Chapter 27

 Nomenclature
• There are three parts which appear always compounds
name:
• 1- Numbering; the number of substituent
• 2- The name of substituent group is derived from the
hydrocarbon by replacing the parent name the ending
“ane” by “yl”
• Example: CH4 Methane replacing “ane” by “yl” Methyl
-CH3 , Propyl –C3 H7.

• 3. The name of Parent Chain

 Common alkyl groups
(C1 through C4)
CH3 CH3 CH2 CH2 CH2 CH3 CH CH2
Methyl Butyl
CH3

CH3 CH2 Isobutyl

Ethyl (2-Methylpropyl)

CH3
CH3 CH2 CH2
CH3 CH2 CH CH3 C
Propyl
CH3 CH3
CH3 CH
sec-Butyl tert-Butyl
CH3 (1-Methylpropyl) (1,1-Dimethylethyl)
Isopropyl
(1-Methylethyl)
 Systematic Nomenclature
 International Union of Pure and Applied
Chemistry
 IUPAC
 Committee on Organic Nomenclature
 The alkanes
CH4 CH3 CH2 CH2 CH2 CH2 CH3
Methane (CH4) Hexane (C6H14)

CH3 CH3 CH3 CH2 CH2 CH2 CH2 CH2 CH3

Ethane (C2H6) Heptane (C7H16)

CH3 CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Propane (C3H8) Octane (C8H18)

CH3 CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Butane (C4H10) Nonane (C9H20)

CH3 CH2 CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Pentane (C5H12) Decane (C10H22)
 Nomenclature of the Alkanes
 Alkanes always have the ending -ane.
 Side chains (substituents) are named as
alkyl groups.
IUPAC nomenclature of alkanes
 identify the longest chain -- parent
 number from the end closest to first branch
 Name the groups attached to the chain, using the
carbon number as the locator.
 Alphabetize substituents.
 Use di-, tri-, etc., for multiples of same substituent
 combine number and name of substituent with
parent name, separating with hyphen
 Longest Chain
• The number of carbons in the longest chain
determines the base name: ethane,
hexane.
• If there are two possible chains with the
same number of carbons, use the chain
with the most substituents.
H3C
CH CH2 CH3
CH3
H3C CH2 C CH CH2 CH2 CH3
CH3
=>
 Number the Carbons
• Start at the end closest to the first attached
group.
• If two substituents are equidistant, look for
the next closest group.

1 CH3 CH3
3 4 5
H3C CH CH CH2 CH2 CH CH3
2 6 7
CH2CH3
(2). Alkyl groups: ( R— )

CH3 CH3CH2 CH3CH2CH2

, ,
methyl ethyl (n-)propyl

CH3CH CH3CHCH2
,
CH3 CH3
isopropyl isobutyl
 CH3
CH3CCH2 neopentyl

CH3
CH3
CH3CH2CH CH3C
,
CH3 CH3
sec-butyl tert-butyl
(s-butyl) (t-butyl)
1 2 3 4 5 6 7 8
CH3CH2CHCH2CHCH2CH2CH3
CH2 CH3
CH3
3-ethyl-5-methyl octane
CH3
H H
H3C1 C2 CH
3 C4 CH3
5
CH3 CH3 2,3,4-trimethyl pentane

Prefixes: di=2 tri=3 tetra=4 penta=5 hexa=6 hepta=7 octa=8

nona=9 deca=10
when two chains of equal length compete for selection as the base chain, choose
the one with more substituents.

CH3
CH2
CH2
7 6H2 5H 4 3
H 2H 1
H3C C C CH C C CH3
CH3 CH3CH3

2,3,5-trimethyl-4-propylheptane
when branching first occurs at an equal distance from either end of the longest
chain, choose the name that gives the lowest number at the first
point of difference; ( if the numbers are the same in both ways,
give the lower first number to the group that will appear first in the
name.)

H 4 H2 3H 2H 1 8
H2 H H2 H2 H 2 1
4
6
H3C 5
C C C C CH3 H3C C 6C 5C C 3C CH2CH3
7

CH3 CH3CH3 CH3 CH2

CH3
2,3,5-trimethylhexane
Not 2,4,5- 3-ethyl-6-methyloctane
Organic nomenclature

4 3 2 1
CH3 CH2 CH CH3

CH3

2-methylbutane
Find the longest continuous
carbon chain
1 2 3
CH3 CH2 CH CH3

CH2 CH3
4 5

3-methylpentane
 You must choose the longest
continuous carbon chain
4 3 2 1
CH3 CH2 CH CH2 CH2 CH3

CH2 CH2 CH3

5 6 7

4-ethylheptane
 Number from the end nearest
the first substituent
CH2 CH3

CH3 CH2 CH2 CH CH CH2 CH3

7 6 5 4 3 2 1
CH3

4-ethyl-3-methylheptane
 Number from the end nearest
the first substituent
CH3

CH3 CH2 CH2 CH CH2 CH CH2 CH3

8 7 6 5 4 3 2 1
CH2 CH3

3-ethyl-5-methyloctane
Use “di-” with two substituents

CH3

CH3 CH CH CH3
1 2 3 4
CH3

2,3-dimethylbutane
Every substituent must get a number

CH3

CH3 CH2 C CH2 CH2 CH3

1 2 3 4 5 6
CH3

3,3-dimethylhexane
 Number from the end nearest
first substituent

CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH2 CH CH3

10 9 8 7 6 5 4 3 2 1
CH3 CH3

2,7,8-trimethyldecane
 Number from the end which has
the “first difference”

CH3

CH3 CH2 CH CH CH2 CH2 CH2 CH CH2 CH3

1 2 3 4 5 6 7 8 9 10
CH3 CH3

3,4,8-trimethyldecane
A More-Highly-Substituted
Carbon Takes Precedence
CH3 CH3

CH3 CH CH2 C CH3

5 4 3 2 1
CH3

2,2,4-Trimethylpentane
 Which end do we number from?

CH3 CH2 CH CH2 CH2 CH CH2 CH3

8 7 6 5 4 3 2 1
CH3 CH2 CH3

3-ethyl-6-methyloctane
 Name following compound
CH3
CH2
CH3
CH3 C CH2

CH2 CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2 CH2

CH2 CH3
CH3

7-(1,1-Dimethylbutyl)-3-ethyl-7-methyldodecane
 Halogens and other side groups
• Flouro –F
• Chloro –Cl
• Bromo –Br
• Iodo –I O
• Nitro –NO2 N
O
 CH 3 CH 2 Br

IUPAC Name Bromo ethane

Common Name “Ethyl bromide”
 CH3

CH3 C Cl

CH3

2-Chloro-2-methylpropane
Common Name tert-Butyl chloride”
CH 3 CH CH CH 2 CH 3

Br CH 3

2-Bromo-3-methylpentane
 Complex Substituents
• If the branch has a branch, number the
carbons from the point of attachment.
• Name the branch off the branch using a
locator number.
• Parentheses are used around the complex
branch name.
1
2

3
1-methyl-3-(1,2-dimethylpropyl)cyclohexane =>
The isopropyl group can be named
as a “complex” substituent

CH3

CH3 CH
2 1

1-methylethyl
 If you can name this,
you can name almost anything!

CH3 CH3

1 CH
2 3 CH
3 4CH2 CH
5 6CH2 C CH3

CH3 CH 7 CH2

CH38 9CH2 CH3

4-isopropyl-2,6,6-trimethylnonane
Now, rename the isopropyl group.
Notice the alphabetical order!
CH3 CH3

CH3 CH CH2 CH CH2 C CH3

1 2 3 4 5 6
CH3 CH CH2
7
CH3 CH2 CH3
8 9
2,6,6-trimethyl-4-(1-methylethyl)nonane
Naming complex substituents --
this one is alphabetized under d

CH3 CH3

CH3 CH CH2 CH
4 3 2 1

1,3-dimethylbutyl
deciding on alphabetical order
for complex groups
 Complex groups are alphabetized under the
first letter of the name
 (1,3-dimethylbutyl) = d
 (1,1,2-trimethylpropyl) = t
 (1-ethyl-1,2-dimethylbutyl) = e
Naming complex substituents

CH3 CH2 CH3

CH3 C CH CH2 CH3

1 2 3 4

2-ethyl-1,1-dimethylbutyl
 This Should Be Fun
CH3

CH3 CH2 C CH2 CH3

1 2 3

CH3 CH2 CH2 CH2 C CH2 CH2 CH2 CH3

1 2 3 4 5 6 7 8 9

CH2 CH2 CH3

5-(1-Ethyl-1-methylpropyl)-5-propylnonane
name this two ways -- (the complex group)
CH3

CH3 C CH3

CH2 CH2 CH2 CH2 CH3

CH3 CH CH2 C CH2

CH2 CH3
CH3

7-(1,1-dimethylethyl)-3-ethyl-7-methyldecane
7-tert-butyl-3-ethyl-7-methyldecane
 degree of substitution
CH3 R R CH2 R

primary (1°) secondary (2°)

R R

R CH R R C R

R
tertiary (3°) quaternary (4°)
 Degree of Substitution

1°
CH3 1°
CH3

CH
1°
CH 3°CH2°2 CH4° CH
3° 3 2° 1° 2
C CH3
1° 3° 2°
CH 3 CH CH2
1° 2° 1°
CH3 CH2 CH3
 Physical properties
• Alkane Molecules contain Carbon and
Hydrogen covalently bonded.
• C – 2.5 electro negativity
• H – 2.1 electronegativity
• Because of little difference there are weak
polar.
• C-H bond will cancel and overall becomes non-
polar
• Because of weak vanderwals forces, The lower
alkanes are volatile.
• As the molecular weight increases their
intermolecular forces increases than melting
point and boiling point increase.
• 2- Alkanes are non polar compound there fore
soluble in non polar solvent, and not soluble
in polar solvent.
 27-2 Alkanes

Slide 71 of 75 Prentice-Hall © 2002 General Chemistry: Chapter 27

 Source Of Alkanes
• Natural gas contains 60-90% Methane
• Oil( Crude oil) is a mixture of many carbon
compounds with different chain length.
• The technique that is used to refine the oil is
called fractional distillation.
• Coal: Is formed by the decomposition of plants
under pressure.
• Cracking: Very long chain alkanes can be broken
into smaller molecules
 Uses of Hydrocarbons
Number of
State Major Uses
C atoms
heating
heating and
and
1-4
1-4 gas
gas cooking
cooking fuel
fuel
liquids,
liquids, solvents,
solvents,
5-7
5-7 (low
(low boiling)
boiling) gasoline
gasoline
6-18 liquids gasoline
6-18 liquids gasoline
jet fuel; camp
12-24 liquids jet fuel; camp
12-24 liquids stove fuel
stove fuel
diesel fuel,
liquids, diesel fuel,
18-50 liquids, lubricants,
18-50 (high boiling) lubricants,
(high boiling) heating oil
heating oil
petroleum jelly,
50+ solids petroleum jelly,
50+ solids paraffin wax
paraffin wax 73
• Petroleum
products and
the ranges of
hydrocarbons
in each
product.
 Chemical Properties Of Alkanes

• Alkanes are saturated hydrocarbons, they

contain enough hydrogen atoms require.
• They are quite inert, do not react readily to
other molecules and atom.
• They make certain reactions under conditions
 1. Substitution Reaction of Alkanes
(Halogenation heat or light)
Initiation:
Cl-Cl Δ or
→h 2 Cl·

Propagation: H3C-H + Cl· → H3C· + HCl

H3C· + Cl2 → H3C-Cl + Cl·

Termination: Cl· + Cl· → Cl-Cl

H3C· + Cl· → H3C-Cl

H3C· + H3C· → H3C-CH3

Slide 76 of 75 Prentice-Hall © 2002 General Chemistry: Chapter 27

2. Reactions of Alkanes Combustion:

Alkanes burn exothermically to produce

carbon dioxide and water if there is a plentiful
supply of oxygen. This is known as complete
combustion.
e.g. CH4 + 2O2  CO2 + 2H2O
Write equations for the complete combustion
of butane and octane.
 17.2 Alkenes
• Alkenes is unsaturated hydrocarbons, which
contains at least one carbon – carbon double
bond.
• General formula Cn H2n there names end
“ene”.
 Alkenes
• also known as olefins
• aliphatic, unsaturated
– C=C double bonds
• formula for one double bond = CnH2n
– subtract 2 H from alkane for each double bond
• trigonal shape around C
– flat
• much more reactive than alkanes
• polyunsaturated = many double bonds

Tro, Chemistry: A Molecular

79
Approach
Tro, Chemistry: A Molecular
80
Approach
 Alkenes
ethene = ethylene propene

H H H H
C C C C
H H H CH3

Tro, Chemistry: A Molecular

81
Approach
 Physical Properties of Alkenes
Name Formula Molar Mass BP, °C Density, g/cm 3
ethene CH2=CH2 28 -104 0.52
propene CH2=CHCH3 42 -47 0.59
1-butene CH2=CHCH2CH3 56 -6 0.59
1-pentene CH2=CH(CH2)2CH3 70 30 0.64
1-hexene CH2=CH(CH2)3CH3 84 64 0.68
1-heptene CH2=CH(CH2)4CH3 98 93 0.70
1-octene CH2=CH(CH2)5CH3 112 122 0.72
1-nonene CH2=CH(CH2)6CH3 126 146 0.73
1-decene CH2=CH(CH2)7CH3 140 171 0.74

Tro, Chemistry: A Molecular

82
Approach
 Common IUPAC

CH2=CH2 ethylene ethene

CH3CH=CH2 propylene propene

CH CH acetylene ethyne

CH3C CH methylacetylene propyne

Shape of ethene molecule
11.1 Structure and Physical Bonding and Geometry
Properties of Two-Carbon Molecules
 Naming alkenes

• 1. Choose the longest chain that contains

double bond.
• 2. Number the carbon atoms from the nearest
the double bond.
• 3. pick the carbon atom with the lowest
number to describe double bond position.
 IUPAC Rules:

Chosing the main chain ：

The longest one containing the double or
triple bond;
Numbering ：
From the end nearest the double or
triple bond and use the first number of the
double bond to locate it;

Naming ： the same as the alkanes.

 CH 3 CH 3
CH 3CHCH 2CHCHCH 2CH 2CH 3
CH
CH 2
4,6-dimethyl-3-propyl-1-heptene
When existing both double and triple bond ，
numbering it from the end nearest the
unsaturated bond ;
if their positions are the same, numbering it by
keeping the number of double bond lower.

H3C HC HC C CH
3-penten-1-yne

CH 3CH CHCHC C CH 3
CH 2CH 3
4-ethyl-2-hepten-5-yne
 For cycloalkenes, we give the double bond
the 1- and 2- position and groups the lowest
numbers.

1
1 2
6
5 2
5 3
4 3 4

1- methylcyclopentene 3,5- dimethylcyclohexene

not 2- methylcyclopentene not 4,6-
Isomers
• Molecules that have the same molecular formula but different
arrangements of their constituent atoms
• There are two forms of isomers:
• Structural isomers
• Stereoisomers

91
 Isomerism

There are three major types of isomerism:

• constitutional isomerism
• geometrical isomerism
• optical isomerism stereoisomerism
Structural isomers

• Constitutional isomers
• isomers that have different bonding arrangements of their atoms
(connectivity)
• usually show very marked differences in physical and chemical
properties
• There are 3 forms of structural isomers: Chain isomers, Positional
isomers and Functional groups isomers

93
 Chain isomers
Pentane, C5H12
CH3
CH3
CH3 CH2 CH2 CH2 CH3 CH3 C CH3
CH3 CH2 CH CH3
CH3

n-pentane isopentane neopentane

94
Positional isomers
C4H9OH
CH3 CH2 CH CH3

CH3 CH2 CH2 CH2 OH OH

butan-1-ol butan-2-ol
CH3

CH3 CH3 C CH3

CH3 CH CH2 OH OH

2-methylpropan-1-ol 2-methylpropan-2-ol
95
Functional groups isomers
C3H6O

O O

CH3 CH2 C CH2 CH CH2 OH

C
H CH3 CH3

propanal propanone 2-propen-1-ol

(aldehyde) (ketone) (alcohol)

96
Stereoisomers

• isomers with identical connectivity but different spatial arrangements of

their atoms
• There are two forms of stereoisomers:
• Geometrical Isomerism
• Optical isomerism

97
 11.3 Geometric Isomers:
A Consequence of Unsaturation

• Carbon-carbon double bonds are rigid

– Orbital shape restricts the rotation around the
bond
– Results in cis-trans isomers
– Requires two different groups on each of the
carbon atoms attached by the double bond
 Naming Geometric Isomers
11.3 Geometric Isomers:
2-butene is the first example of an alkene which
can have two different structures based on
restricted rotation about the double bond

H CH3 CH3 CH3

Consequence of

C C C C
Unsaturation

CH3 H H H
trans-2-butene cis-2-butene
Chirality
• Chirality (Greek: cheir,hand)
• refers to objects which are related as non–superimposable mirror
images
• the term derives from the fact that left and right hands are examples of
chiral objects.

100
Chiral molecules

• The most common type of chiral molecule contains a tetrahedral carbon

atom attached to four different groups (asymmetric carbon).
• Such a molecule can exist as two different compounds (stereoisomers) that
are nonsuperimposable mirror image of each other.
• Such stereoisomers are call enantiomers (Greek: enantio,opposite)

101
Enantiomes

• stereoisomers that are nonsuperimposable mirror images of each other

• Enantiomers have opposite configurations.
• Example: Alanine is a chiral molecule and exists as a pair of enantiomers

COOH COOH

CH3 H3C
H2N NH2
H H
Enantiomers of alanine
102
Enantiomes
• Optical isomers
• have identical chemical and physical properties in a symmetric environment
except for their ability to rotate plane-polarized light by equal amounts but in
opposite direction
• optically active
Racemic mixture
• 50/50 mixture of two enantiomers
• optically inactive

103
Optical Rotation

• The degree (angle) of rotation is measured using a polarimeter and has a

specific value for each optically active substance
• If the rotation is to the right (clockwise), the substance is dextrorotatory,
(+) or (d) (Latin: dexter, right)
• If the rotation is to the left (counterclockwise), the substance is levorotatory,
(-) or (l) (Latin: laevus, left)

104
polarizer
Polarimeter analyzer
sample

plane-polarized dextrorotatory levorotatory optically

(d) or (+) (l) or (-) inactive

optically
active

105
Optical Rotation
• The magnitude of the rotation of an enantiomer is reported as its specific
rotation
• Specific rotation is dependent on:
• the wavelength of the light used
• the length of the polarimeter tube
• the temperature
• the nature of solvent
• the concentration

106
Relative configuration

Absolute configuration and its notation

• The earliest method of distinguishing between enantiomers was the sign of

optical rotation:
• d- or (+)-form
• l- or (-)-form
• This does not say anything about configuration.
• There is no relationship between a particular configuration and the direction of
rotation.

107
Example: Lactic acid

• There are two enantiomers of lactic acid.

• One rotates the plane-polarized light to the right and the other to the left and
are labeled:
(+)-lactic acid or d-lactic acid
(-)-lactic acid or l-lactic acid

H H
*
CH3CHCOOH

OH HO
OH HOOC COOH
CH3 H3C

108
• The two configuration of lactic acid are shown below, but the question
is which one corresponds to (+)-lactic acid and which to (-)-lactic acid.

H H

OH HO
HOOC COOH
CH3 H3C

109
 Some groups:

CH2 CH2 CH2 CH Vinyl

CH3 CH CH Propenyl

CH3 CH CH2 CH2=CHCH2— Allyl

CH2 C Isopropenyl
CH3
 II. Isomerism

Carbon-chain isomers
Functional isomers Constitutional
Alkenes:
isomerism
Positional isomers

Cis-trans Stereo
isomers isomerism （ configuratio
nal ~ ）
 CH3
CH3-CH2-CH=CH2 CH3-CH=CH-CH3 CH3-C= CH2

Positional isomers Carbon-chain isomers

Cis-trans isomers
CH3 CH3 CH3 H
C=C C=C
H H H CH3
cis-2-butene trans-2-butene
mp:-139 ℃,bp 4 ℃ mp -117 ℃, bp 1℃
 Chemical properties
• 1. Combustion
• C2 H4 + 2O2 (g) → 2CO2

• Addition: A reaction in which two molecules

combine to yield a single molecule of product.
 Reactions of Alkenes
1. Addition of hydrogen (hydrogenation)
Alkenes react with hydrogen in the
presence of a nickel catalyst at 180 °C
to form an alkane. e.g.
H H H H
C=C + H2 H–C–C–H
H H H H
C2H4 + H2  C2H6

ethene ethane
2. Addition of halogens (halogenation)
Halogens react with alkenes at room temperature and pressure in a non-polar
solvent to form a dihalogenoalkane.
e.g.

H H H H
C=C + Br2 H–C–C–H
H H Br Br
C2H4 + Br2  C2H4Br2
ethene 1,2-dibromoethane
Bromine water is used as a test for unsaturation.
In the presence of an alkene, bromine water turns from red brown to colourless. Alkanes do
not react with bromine water.
 Bromine Water Test For Alkenes

C=C + Br2(aq) –C–C–

Br Br
colorless amber colorless
3. Reaction with hydrogen halides (hydrohalogenation)
Alkenes react with hydrogen halides (HCl, HBr etc.) to form halogenoalkanes. The
reaction occurs at room temperature and pressure. e.g.

H H H H
C=C + HBr H–C–C–H
H H H Br
C2H4 + HBr  CH3CH2Br
ethene bromoethane
• 3. Oxidation: Alkenes are oxidized by cold,
slightly alkaline potassium permanganate (Mn
IV) to make substance called 1,2 diols
containing two OH groups an adjacent carbon
atoms.
• KMnO4 solution turns from purple to brown
H H H H
C=C + KMnO4 H–C–C–H
H H OH OH
 4. Polymerization
• Is the process of simple units combine to form
large molecules.
• Monomer : Simple unit
• Polymer : Large molecule
• n(CH2 = CH2)Monomer → CH2 - CH2 - CH2 -Ploymer
 Alkynes
• Unsaturated hydrocarbons that contain
carbon-carbon triple. General formula CnH2n-2
• First member C2 H2 Ethyne old name
Acetylene
 Aromatic Hydrocarbons
• contain benzene ring structure
• even though they are often drawn with C=C,
they do not behave like alkenes

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Approach
 Resonance Hybrid
• the true structure of benzene is a resonance
hybrid of two structures

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Approach
 Naming Monosubstituted Benzene
Derivatives
• (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

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Approach
 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

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 Naming Disubstituted
Benzene Derivatives
• number the ring starting at attachment for first
substituent, then move toward second
– order substituents alphabetically
– use “di” if both substituents the same
F CH3
3 1 CH3
2 2
1 Br
1-bromo-3-fluorobenzene 1,2-dimethylbenzene

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Approach
 Naming Disubstituted
Benzene Derivatives
• alternatively, use relative position prefix
– ortho- = 1,2; meta- = 1,3; para- = 1,4
CH3 CH3 CH3
Cl

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

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Approach
 Practice – Name the Following

F Br

Br
Cl

Tro, Chemistry: A Molecular

129
Approach
 Practice – Name the Following

F Br

Br
Cl

1-chloro-4-fluorobenzene 1,3-dibromobenzene
or meta-dibromobenzene
or m-dibromobenzene

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Approach
 Polycyclic Aromatic Hydrocarbons
• contain multiple benzene rings fused together
– fusing = sharing a common bond

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Approach
 Reactions of Aromatic Hydrocarbons
• most commonly, aromatic hydrocarbons
undergo substitution reactions – replacing H
with another atom or group

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Approach