Introduction

A. History
1807- Berzelius proposed that compounds
from living things were organic and that
all others were inorganic.

– scientist then were certain that organic

compounds could be produced only
within living systems
Living things possessed a vital force
as a result of their origin. This belief
came to be known as the
VITAL FORCE THEORY

-more than 20 years later in 1828, Friedrich Wohler- former student of Berzelius, was able to synthesize
 Urea ( H2NCONH2) using inorganic material.

He heated an aqueous solution of two

inorganic compounds:
NH4Cl + AgNCO--- (NH2)2CO + AgCl
Urea, an organic
component of the
urine of mammals

This event disproved the VFT

 The weight of evidence was against the VFT and it became clear that the only distinguishing characteristic of organic compound was the presence of the
element CARBON
 Organic Chemistry

• Is the chemistry of the compounds of

Carbon.
• Organic compounds are the chemical
basis for life itself, as well as an
important component of the basis for
our current high standard of living
• Organic molecules includes proteins,
carbohydrates, enzymes, hormones
• Organic compounds also include natural gas
petroleum, coal, gasoline and many synthetic materials
such as dyes,plastics,and clothing fibers.

• Organic compounds involves only a few other

elements- H,O and N, others may contain S, X (F, I Br or
Cl) or P.

• Organic Chemistry concentrates on C ,just 1 of the 118

known elements.
75% of the earth’s crust is composed of just 2
elements: O and Si which are components of
silicate minerals, clays and sand. It is not even
among the top 10 most abundant element, it
is merely one of the components making up
the remaining 0.9 % of Earth’s crust.
Why do we pay special attention to just one
element from among 118?
Reasons:
1. largely historical- “vital force theory
doctrine”
2. “10 million of organic compounds were
discovered by chemist and an estimated
10,000 new ones each year are discovered or
prepared in the laboratory.

3. Carbohydrates, lipids, proteins, enzymes,

nucleic acid, hormones, vitamins and almost
other important chemicals in living systems
are organic compounds.
4. Generally differ from inorganic compounds in
many of their properties.
Property Organic Inorganic
Bond Covalent Ionic bonding
bonding
State Maybe gases, Most are solids
liquid, or solids with high
with low melting and
melting and boiling
boiling points,high
point,low densities
densities
Solubility in Most are not Many are soluble
water soluble
Solubility in Generally soluble Almost all are
organic insoluble
solvents
(diethyl ether,
toluene,
dichlorometha
ne
Conductivity Do not conduct Conductor of
electricity electricity
Combustibility Almost all burn, Very few burn,
flammable gen. non
flammable
Rate of Slow- due to Fast since
reactions slower breakage reactions
of covalent between ions are
bonds fast
Structural Complex Simple
Arrangement
Stability with Less stable .More stable and
Heat towards heat or very high
decomposes temperature
easily when requires to
decompose
Activity Less reactive More reactive
• The terms Organic and Inorganic continue
to be used in classifying compounds, but
the definitions of these terms no longer
reflect their historical origins.

ORGANIC Chemistry is the study of

hydrocarbons ( compounds of C and H) and
their derivatives.
Compounds like CO, carbon monoxide
CO2, carbon dioxide;H2CO3, carbonic acid
HCO3-, bicarbonate; CN-, cyanide
CNO-, cyanate ; CO3- carbonate
are considered inorganic because their properties resemble those inorganic compounds.
 BONDING CHARACTERISTICS OF
THE CARBON ATOM

Carbon can meet this four-bond

requirement in three different ways:

• By bonding to 4 other atoms.(This

situation requires the presence of 4
single bonds).
• By bonding to 3 other atoms.(This
requires the presence of two single
bonds and one double bond).

• By bonding to 2 other atoms. (This

situation requires the presence of
either 2 double bonds or a triple
bond and a single bond.
 Sources of Organic Compounds
Two Principal Ways to obtained organic
compounds:

1. Isolation from nature

Living organisms are chemical
“factories”.Each plant and animal, even
microorganism such as bacteria, makes
thousands of org compound by a p’xs called
biosynthesis.
One way to get organic compounds is to
extract them from biological sources like:

a. Plants
– ex. Grapes –tartaric acid
Extract of the bark of the
Pacific yew, TAXUS BREVIFOLIA (a slow
growing tree in the old forest of the
Pacific Northwest.---- drug TAXOL
(effective in treating ovarian and breast
cancer)
b. Animals- protein

c. Natural gas
- often encountered from drilling
wellsfrom petroleum
- contains 50-94%methane,
ethane, etc......
d. Petroleum- a thick, viscous liquid
mixture of thousands of compounds,
most of them are hydrocarbons (from
the decomposition of marine plants and
animals.

e. Oil shale distillate (a rock from which an

oil can be recovered by distillates).

f. Coal – indirect source of aromatic HC

2. Synthesis in the laboratory
- compounds made in the laboratory are
identical to those found in nature, 100% pure.

- Pure ethanol made by chemist = same physical

and chemical property as the pure ethanol
prepared by distilling wine.
 Classification based on the
functional group found in the
molecule
 Classification based on skeletal carbon
structure of the compound
 a. Alicyclic
- close; close chain structure; ring.
 b. Aliphatic
– non aromatic compound; fats
- made up of open chain structure
(Straight chain & Branched chain)
 c. Aromatic
- close chain (with benzene ring)
 d. Heterocyclic
- closed chain but has other atoms
in it.
 Classification based on the kind of
bond in the compound
1. Saturated hydrocarbon – long chain HC with
single bonds.
Ex.
C-C-C-C-C-C-C-C-C

2. Unsaturated hydrocarbon – with double or

triple bond (multiple bond)
Ex.
C-C-C=C-C-C
 Kinds of organic formulas

A. General Formula – represents the entire

series of compound.
B. Molecular Formula – represents the actual
no. of each kind of atom present in a
compound
C. Structural Formula- is a two-dimensional
structural representation that shows how the
various atoms in a molecule are bonded to
each other.
Types of structural formula:
C1. Expanded structural formula- is
the structural formula that shows all
atoms in a molecule and all bonds
connecting the atoms
Ex.
 C2. Condensed structural formula- is a structural formula that uses groupings of atoms, in which central atoms and the atoms connected to them are written as a group, to convey
molecular structural information.
Ex. CH3-CH2-CH2-CH2-CH3
C3. Skeletal structural formula-is a
structural formula that shows the
arrangement and bonding of
carbon atoms present in an organic
molecule but does not show the
hydrogen atoms attached to the
carbon atoms.

C-C-C-C-C-C
D. Line angle formula- in which carbon atoms are implied at the corners and ends of lines (Line represents a C-C bond) and each carbon atom is understood to be attached to enough hydrogen
atoms to give each carbon atom four bonds.
Classes of Carbon and Hydrogen Atoms
Primary carbon atom -carbons attached
to only one carbon atom.

Secondary carbon atom- carbon attached to

two other carbon atoms.

Tertiary carbon atom- carbon attached to

three other carbon atoms.

Quaternary carbon atom- carbon attached

to four other carbon atoms.
Primary Hydrogen
A primary (1°) hydrogen is a
hydrogen atom residing on
a primary carbon in an organic
species.

Secondary
Hydrogen
A secondary (2º) hydrogen is a
hydrogen atom residing on a
secondary carbon in an organic
species.
Tertiary Hydrogen
A tertiary (3°) hydrogen is a hydrogen
atom residing on a tertiary carbon in
an organic species
 Isomerism
Isomers-compounds that have the same
numbers and kinds of atoms but differ in the
way the atoms are arranged( different in
structure).
A. Constitutional Isomers
(Chain /Skeletal)

C5=using CnH2n+2
 Skeletal isomers are constitutional
isomers that have the same functional
groups but differ from each other in the
connectivity of the carbon skeleton.
Butyl alcohol (1) and isobutyl
alcohol (2) are constitutional isomers
containing the same functional groups,
namely the alcohol group.
 Skeletal isomerism of
Pentane

N-Pentane Isopentane Neopentane

Chain Isomerism
In chain isomerism, or skeletal isomerism,
components of the (usually carbon) skeleton are
distinctly re-ordered to create different structures.
Pentane exists as three isomers: n-pentane (often
called simply "pentane"), isopentane (2-
methylbutane) and neopentane (dimethylpropane).
B. Functional Isomers
- when substances have the same
molecular formula but different
functional groups.
• Alcohol & ether
• Ester & carboxylic acid
• Ketone & aldehyde
Ketone & Aldehyde

Propanal Propanone C3H6O

Aldehydes and ketones

both have the
carbonyl group C=O. In
ketones this is attached to
two carbon atoms; in
aldehydes it is attached to
1 or 2 hydrogen atoms.
Carboxylic acid/ Ester
RCOOH/ RCOOR’

Alcohol/ Ether
ROH/ROR’
 C. Geometric Isomers

Geometric isomers are two or more

coordination compounds which contain
the same number and types of atoms,
and bonds (i.e., the connectivity between
atoms is the same), but which have
different spatial arrangements of the
atoms.
Geometric isomer
(alkene)
cis and trans
Kinds of Covalent Bond
 Sigma bond
- Covalent bond that is formed thru
end to end overlapping.
 Pi bond

- Covalent bond that is formed thru

lateral /sideways overlapping.
 Kinds of
hybridization
 1. Tetrahedral
(Tetragonal)

- Mixing or blending of an “s” with “3p”

orbitals (leading to “4sp3”)
- Alkane (CnH2n+2)
- 109.5 degree (bond angle)
 2. Trigonal
- Mixing or blending of an “s” with “2
p” orbitals (leading to “sp2”)
- Alkene (CnH2n)
- 120 degree
 3. Linear (Digonal)
- Mixing or blending of an “s” with “1
p” orbital (leading to “2sp”)
- Alkyne (CnH2n-2)
- 180 degree
Organic Reactions
 Substitution
- Replacement of one atom by groups or
other.
- Occurs when two reactants exchange
to give two new product.
- Involves no change in the number of
atoms or group of atoms attached to
carbon.
- Sigma bond remains as sigma bond.
Substitution reaction (also known
as single displacement
reaction or single replacement
reaction) is a chemical reaction
during which one functional group in
a chemical compound is replaced by
another functional group
 Addition
- Addition of one molecule across of a
multiple bond in another molecule.
- Involves an increase in the number
of groups attached to carbon atom.
- Pi bond is converted to sigma bonds.
In organic chemistry, an addition reaction
is, in its simplest terms, an organic
reaction in which two or more molecules
combine to form a larger molecule.
Addition reactions are limited to chemical
compounds that have multiple bonds,
such as molecules with carbon-carbon
double bonds (alkenes) or with triple
bonds (alkynes).
 Elimination
- The intra molecular loss (within the
molecule) of a small molecule from a
larger one, with simultaneous
formation.
- Involves a decrease in the number of
atom or groups of atoms attached to
the carbon.
- Sigma bond is converted to Pi bond.
An elimination reaction is a
type of organic reaction in
which two substituents are
removed from a molecule in
either a one or two-step
mechanism.
 Condensation
- Is when a small molecule (usually
H2O) is eliminated from two or more
larger molecule.
In a condensation reaction, two
molecules or parts thereof combine,
releasing a small molecule. When this
small molecule is water, it is known as
a dehydration reaction. Other possible
lost molecules include hydrogen
chloride, methanol, and acetic acid
Isomerization
In chemistry isomerization (also isomeri-
sation is the process by which
one molecule is transformed into another
molecule which has exactly the same
atoms, but the atoms have a different
arrangement e.g. A-B-C → B-A-C (these
related molecules are known as isomers.
 The Saturated Hydrocarbon
Alkanes

Compounds that contain only carbon and

hydrogen are known as hydrocarbons.
Those that contain as many hydrogen
atoms as possible are said to be saturated.
The saturated hydrocarbons are also
known as alkanes.
The simplest alkane is methane: CH4. The
Lewis structure of methane can be
generated by
combining the four electrons in the valence
shell of a neutral carbon atom with four
hydrogen atoms to form a compound in which
the carbon atom shares a total of eight valence
electrons with the four hydrogen atoms.
  Alkanes
• As the name implies, hydrocarbons are
compounds that contain carbon and
hydrogen only.
• 109.5⁰ bond angle, with tetrahedral type of
hybridization
• It is also known as the “paraffin series”
 Physical Properties, Sources and Uses of
Alkanes
• Methane, ethane, propane and butane are gases at room
temperature. They are used for fuels, n-pentane is liquid; the
higher alkanes are solid at room temperature.
• Boiling point and melting point increases with increasing
number of C atoms.
• They are insoluble in water and in cold H2SO4 but very soluble
in organic solvents.
• They are inert with many reagents, they do not undergo
addition reactions.
• Their principal source is petroleum.
• Halogenated hydrocarbon are useful in the dry cleaning
industry due to their ability to dissolve dirt and grease.
• Haloalkanes known as freons are used as refrigerants but they
can damage the ozone layer.
 General formula
• The general formula for alkanes is
CnH₂n+₂

When n represents the number of carbon

atoms. That is, if a compound contains n
carbon atoms, the number of hydrogen atoms
is twice n plus two more.
 Rules in IUPAC system
1. Identify the longest continuous carbon chain
(parent chain)
2. Number the carbon atoms in the parent
chain from the end of the chain nearest to
the substituent
3. If only one alkyl group is represent, name
and locate it (by number, and prefix the
number, and name to that of the parent
carbon chain.)
4. If two or more of the same kind of alkyl
group are present indicate the no. using di, tri,
tetra, penta, etc
5. When 2 kinds of alkyl groups are present
in the carbon chain, number its group
separately and list the name of the alkyl in
alphabetical order.
Greek Prefixes
2. di
3. tri
4. tetra
5. penta
6. hexa
7. hepta
8. octa
9. nona
10. deca
Other Substituents:
• Chlorine – Chloro = Cl
• Bromine – Bromo = Br
• Iodine – Iodo = I
• Fluorine – Fluoro = F
• NO₂ – Nitro = NO₂
• NH₂ – Amino = NH₂
 Alkyl Groups
When a hydrogen atom is removed from an
alkane, an alkyl group is formed. The names alkyl
groups are obtained by changing the ending of the
name from
-ane to –yl. The alkyl group of one carbon atom
formed from the alkane methane is called the
ethyl group. The alkyl group of three carbon
atoms formed from propane is called propyl.
 The Gas
Formula Name
CH 4 CH 4 methane
C 2H 6 CH 3 CH 3 ethane
C 3H 8 CH 3 CH 2 CH 3 propane
CH 3 CH 2 CH 2 CH
C 4 H 10 butane
3
 The Liquid
Formulas Name
C 5 H 12 CH 3 (CH 2 ) 3 CH 3 pentane
C 6 H 14 CH 3 (CH 2 ) 4 CH 3 hexane
C 7 H 16 CH 3 (CH 2 ) 5 CH 3 heptane
C 8 H 18 CH 3 (CH 2 ) 6 CH 3 octane
C 9 H 20 CH 3 (CH 2 ) 7 CH 3 nonane
C 10 H 22 CH 3 (CH 2 ) 8 CH 3 decane
C 11 H 24 CH 3 (CH 2 ) 9 CH 3 undecane
C 12 H 26 CH 3 (CH 2 ) 10 CH 3 dodecane
C 13 H 28 CH 3 (CH 2 ) 11 CH 3 tridecane
C 14 H 30 CH 3 (CH 2 ) 12 CH 3 tetradecane
C 15 H 32 CH 3 (CH 2 ) 13 CH 3 pentadecane
C 16 H 34 CH 3 (CH 2 ) 14 CH 3 hexadecane
 The Solid
Formulas Names

C 18 H 38 CH 3 (CH 2 ) 16 CH 3 octadecane

C 19 H 40 CH 3 (CH 2 ) 17 CH 3 nonadecane

C 20 H 42 CH 3 (CH 2 ) 18 CH 3 eicosane
All alkanes are colorless and odorless.
Table of Alkanes
Alkane Melting Density
Formula Boiling point
[°C] point [g·cm−3] (at
[°C] 20 °C)

Methane CH4 −162 −182 gas

Ethane C2H6 −89 −183 gas

Propane C3H8 −42 −188 gas
Butane C4H10 0 −138 gas
Pentane C5H12 36 −130 0.626 (liquid)
Hexane C6H14 69 −95 0.659 (liquid)
Heptane C7H16 98 −91 0.684 (liquid)
Alkane
Alkane chemical reaction

1. Combustion
The combustion of carbon compounds, especially hydrocarbons,
has been the most important source of heat energy for human
civilizations throughout recorded history. The practical importance
of this reaction cannot be denied, but the massive and
uncontrolled chemical changes that take place in combustion
make it difficult to deduce mechanistic paths. Using the
combustion of propane as an example, we see from the following
equation that every covalent bond in the reactants has been
broken and an entirely new set of covalent bonds have formed in
the products. No other common reaction involves such a profound
and pervasive change, and the mechanism of combustion is so
complex that chemists are just beginning to explore and
understand some of its elementary features.
CH3-CH2-CH3 + 5 O2 ——> 3 CO2 + 4 H2O + heat
2. Halogenation
Halogenation is the replacement of one or
more hydrogen atoms in an organic compound
by a halogen (fluorine, chlorine, bromine or
iodine). Unlike the complex transformations of
combustion, the halogenation of an alkane
appears to be a simple substitution reaction in
which a C-H bond is broken and a new C-X
bond is formed. The chlorination of methane,
shown below, provides a simple example of
this reaction.
CH4 + Cl2 + energy ——> CH3Cl + HCl
 Nitration
• Addition of nitric or nitrous acid
 Isomerization
• Rearrangement of alkane in the presence
aluminum chloride (catalyst)
Preparations of Alkanes
 1. Hydrogenation
• Reduction of alkenes
• With the presence of Pd, Pt and Ni (catalyst)
 2. Hydrolysis of Grinard reagents
• Organometallic compounds (Mg)
• Very useful and versatile organic compounds
• General Equation: R-X RMgX
 3. Reduction of Alkyl halides by metal and
acid
• R-X + H2 R-H + HX
Cycloalkanes

Alkanes also exist in the shape of a ring. Such

structures are called cykloalkanes. They are named by
placing the prefix cyclo– before the name of the
corresponding continuous-chain alkane. Thus, the
cyclic alkane of three carbons is called cyclo-propane.
Cycloalkanes: Physical Properties

Cyclopropane and cyclobutane are gases at

room temperature while cyclopentane is
already liquid at this temperature. Only van
der Waals interactions play an important role
in saturated hydrocarbons. Generally, alkanes
are not very reactive. mixtures with air
(oxygen). Solubility in water is very low.
However, protonations, oxygenations,
pyrolysis, radiolysis, and photolysis are
possible under drastic conditions.
Oxidation of alkanes can be carried out
electrochemically. Lower cycloalkanes are
especially flammable and form explosive
Alkene
• An alkene is a molecule made up entirely
of carbon and hydrogen where one or
more carbon atoms are connected by
double bonds.
• The general formula for an alkene is
CnH2n where n is the number of carbon
atoms in the molecule.
 Physical state
• Ethene, Propene, and Butene exists as
colorless gases. Members of the 5 or more
carbons such as Pentene, Hexene, and
Heptene are liquid, and members of the 15
carbons or more are solids.
 Density
• Alkenes are lighter than water and are
insoluble in water due to their non-polar
characteristics. Alkenes are only soluble in
nonpolar solvents.
 Solubility
• Alkenes are virtually insoluble in water, but
dissolve in organic solvents. The reasons for
this are exactly the same as for the alkanes.
 Boiling Points
• The boiling point of each alkene is very similar
to that of the alkane with the same number of
carbon atoms. Ethene, propene and the
various butenes are gases at room
temperature. All the rest that you are likely to
come across are liquids. Boiling points of
alkenes depends on more molecular mass
(chain length). The more intermolecular mass
is added, the higher the boiling point.
 Uses
• Ethene is the most important organic feedstock in the
chemical industry. Ethene is produced from natural gas and
crude oil by cracking. It is used as feedstock for many
chemical products such as polyethylene, vinyl chloride,
styrene, ethanol, acetaldehyde, and many more.
• Propene, the second most important feedstock for organic
products with an estimated worldwide production in 2000
of about 50 million metric tons, is mainly used for the
production of polypropylene and various oxidation
products such as butanol, acrylic acid, acrolein, acrylic acid
ester, glycerol.
• Butadiene with a worldwide production in 1953 of about
8.5 million metric tons is mainly used for the production of
various synthetic rubbers.
• CODE 1 (PET or PETE), qualities: thin and clear
– Common usage: bottles of water, cooking oil,
peanut butter, soda
– Studies indicate that this plastics is safe for one-
time use only.
• CODE 2 (HDPE – High-Density Polyethylene)
– Qualities: thick and opaque
– Common usage: milk and water jugs, juices
bottles, containers for detergent, shampoo and
motor oils
– limit how often you refill containers made of
HDPE. It can recycled one time
• CODE 3 (PVC – Polyvinyl Chloride)
– Qualities: may be rigid or flexible
– Common usage: mattress covers and commercial
grade plastics wrap
– Avoid it. The manufacture of PVC creates dioxin, a
potent carcinogen that contaminates humans
• CODE 4 ( LDPE – Low –Density Polyethylene)
– Qualities: soft and flexible
– Common usage: grocery store bags, plastics wrap
for household use and garbage bags
– LDPE is one of the safer plastics
• CODE 5 (PP – Polypropylene)
– Qualities: hard but flexible
– Common usage: Ice cream and yogurt containers,
drinking straws, syrup bottles and diapers
– PP is one of the safer plastics, but be sure to
recycle wherever possible.
• CODE 6 (PS – Polystyrene)
– Qualities: rigid
– Common use: Styrofoam, coffee cups and meat
trays
– Avoid it. PS can leach styrene, a known neurotoxin
with other harmful effects
Synthesis and Reactions

Alkenes
• Addition of H-X to alkenes
(hydrohalogenation)
– Markovnikov Rule – in the addition of H-X to
an alkene the H attaches to the carbon with
fewer alkyl substituents and the X (Cl,Br or
I) attaches to the carbon with more alkyl
substituents
H
H3C +
CH3
HCl H3C
CH3

Cl
 • Hydration – addition of water in the presence
of acid catalys (H +)
– Follows the Markovnikov’s rule

OH
CH3 CH3
H3C CH3 + H 2O H3C CH3

CH3 CH3 H
• Halogenation – addition of X2 to the double
bond to produce a dihalo-substituted alkane.
– Anti-addition produces a trans substance (cyclo
alkanes)
• Hydrogenation – addition of H2 to an alkene.
– Produces an alkane
– Reduction reaction and heterogenous reaction
since the catalyst used is a metal (Pd, Ni, or Pt)
• Combustion – reaction with oxygen to
produce heat, water and carbon dioxide.
• Oxidation – Reduction - increases in the
number of oxygen or decreases in the number
of hydrogen.
– Hydroxilation – addition of hydroxyl group ( -OH)
to produce 1,2 dialcohol or 1,2 – diol (glycol)
• Happens when an alkene is treated with potassium
permanganate in a basic medium.
• Cleavage – carried out in the presence of
potassium permanganate in an acidic medium
which leads to the formation of carbonyl
compounds (ketones, carboxylic acid or
carbon dioxide)
Alkynes
• is an unsaturated hydrocarbon
containing at least one carbon—carbon
triple bond.
• The simplest acyclic alkynes with only
one triple bond and no other functional
groups form a homologous series with
the general chemical formula CnH2n−2
 Properties
• Essentially the same on the alkenes and
alkynes.
• Insoluble in water but quite soluble in the usual
organic solvent.
• Less dense in water
• Boiling points show unusual increase with
increasing carbon number.
• Have nearly the same boiling points on that
alkanes and alkenes.
 Uses
• Propyne, also known as methylacetylene, is
commonly used as a substitute for acetylene as
fuel for welding torches.
– It is also being investigated as possible fuel for rockets
in space craft
• Acetylene, also referred to as ethyne, is one of
the most well-known and widely used alkynes.
– Acetylene is very useful because it can undergo
several chemical reactions that are needed in
manufacturing products in different industries.
– Acetylene is an important raw material in the
chemical industry to produce polyethyelene
 Reaction of Alkynes
1. Addition of H2 - alkynes are easily converted
to alkane by reaction with 2 equivalent of H2
over a palladium catalyst.

H3C Pd H3C H 2 H3C

CH3 + H2 +
CH3 CH3
 2. Halogenation
• 2 moles of reagents is consumed for each
triple bond, producing a tetrahaloalkane

Cl Cl
C l2 Cl
HC CH3 CH3 C l2 CH3
Cl
Cl Cl
 3. Hydrohalogenation
• Two moles of hydrogen halides add to alkynes
in sequence and in accordance with
Markovnikov’s rule. In the first stage an alkenyl
halide is formed and in the second stage a
dihaloalkane is formed.
• In the presence of peroxides HBr and HI to
alkynes in accordance in Kharasch addition
(anti-Markovnikov)
 Cl
Cl
H3C HCl H3C HCl H3C
Cl
CH2
CH CH3

H
H3C H Br
CH H3C
Peroxide
Br
 4. Addition of Water
• Takes place when alkyne is treated with dilute
sulfuric acid in the presence of mercuric
sulfate catalyst.
• Follows the Markovnikov’s rule to form an –
enol.
• Rearranges quickly to form ketone

H 2 SO 4
H3C CH H3C CH2 + H3C CH3
H gS O 4
OH O