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Introduction to Organic Chemistry

Organic chemistry is the study of compounds that contain the element carbon.

The word organic is used in several different contexts. Scientists of the


18th and 19th centuries studied compounds extracted from plants
and animals and labeled them organic because they had been obtained
from organized (living) systems. Organic fertilizer is organic in the
original sense that it comes from a living organism.
There is no universal definition of organic foods, but the term is generally
taken to mean foods grown without the application of pesticides or synthetic
fertilizers.
When referring to organic chemistry, however, we mean the chemistry of
carbon-containing compounds.
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Introduction to Organic Chemistry

Before this reaction scientists believed that a special vital force


needed to form organic compounds

silver cyanate,

But in 1828 the German chemist Friedrick Whler proved


that this idea is wrong and he was able to prepare urea
an organic compound present in blood and urine
from in organic compounds.
It was a turning point and chemists prepared thousands of other organic
compounds
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Introduction to Organic Chemistry
In essence, organic chemistry is the study of the compounds of one element
(carbon), and inorganic chemistry is the study of the compounds of the other
116 elements.
This unequal partitioning occurs because there are approximately 7 million
organic compounds and only an estimated 1.5 million inorganic compounds
This is an approximately 5:1 ratio between organic and inorganic compounds.

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Why Carbon?!
In compound formation, four additional valence electrons are needed to give carbon
atoms an octet of valence electrons. These additional electrons are obtained by electron
sharing (covalent bond formation). The sharing of four valence electrons requires the
formation of four covalent bonds.
Carbon can meet this four-bond requirement in three
different ways:

1. By bonding to four other atoms. This situation requires


the presence of four single bonds.

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Carbon can meet this four-bond requirement in three different ways:
2. By bonding to three other atoms. This situation requires the presence of two single
bonds and one double bond.

3. By bonding to two other atoms. This situation requires the presence of either two
double bonds or a triple bond and a single bond.

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Organic
Compounds

HYDROCARBON
HYDROCARBONS DERIVATIVES
Containing only C (C, H, other
and H element)

SATURATED UNSATURATED
HYDROCARBONS HYDROCARBONS
carbon-to-carbon carbon-to-carbon
bonds are single multiple bonds
bonds

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Difference between Organic and Inorganic compounds

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Functional Groups

A functional group is a group of atoms within a molecule that has a


characteristic chemical behavior.
The chemistry of every organic molecule, regardless of size and complexity, is
determined by the functional groups it contains.

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STRUCTURAL FORMULAS
A structural formula is a two-dimensional structural representation that shows
how the various atoms in a molecule are bonded to each other.
Structural formulas
expanded structural formulas condensed structural formulas.

It is a structural formula It is a structural formula


that shows all atoms in a that uses groupings of atoms, in which
molecule and all central atoms and the atoms connected
bonds connecting the to them are written as a group, to
atoms. convey molecular structural
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information. 13
Sometimes these structures are further simplified by using parentheses around like groups.
Two CH2 groups bonded together become (CH2)2. Two CH3 groups bonded to the same
carbon become (CH3)2C

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3 D structure

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Skeletal Structures

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Alkanes
Alkanes are hydrocarbons having only C - C and C -H single bonds. The carbons of an alkane can
be joined together to form chains or rings of atoms. Usually called aliphatic hydrocarbons.

Alkanes that contain chains of carbon atoms but no rings are called acyclic alkanes. An acyclic
alkane has the molecular formula CnH2n + 2, where n is the number of carbons it contains.
Acyclic alkanes are also called saturated hydrocarbons because they have the maximum
number of hydrogen atoms per carbon. They also, can be Unsaturated hydrocarbons.

If alkanes are acyclic, they called cycloalkanes. Cycloalkanes contain carbons joined in one or
more rings. Since a cycloalkane has two fewer Hs than an acyclic alkane with the same number
of carbons, its general formula is CnH2n.

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Alkanes

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The Structures of Alkanes
Each carbon atom in an alkane molecule has four covalent bonds that are arranged in a
tetrahedral shape about the atom.

The family of alkanes shown in the table (previous slide) is an example of a


homologous series. A homologous series is a family of compounds in which each
member differs from the one before it in the series by one methylene (CH2)
group . The members of a homologous series are called homologs .
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Alkanes
Alkanes contain only nonpolar covalent bonds, are nonpolar molecules, and are attracted
to one another by London forces.
The more carbon atoms in a normal alkane, the higher its boiling point. The reason for this
is that the longer the alkane, the greater its surface area and the stronger the London force
that holds it to other molecules. Boiling points increase with strengthened intermolecular
forces, because this physical change involves pulling molecules in the liquid phase apart
from one another and moving them into the gas phase. An increase in London forces is also
associated with a rise in melting point, because more energy (a higher temperature) is
required to loosen the attraction between molecules in the solid phase.

("strong") (Weak)
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Alkanes
Alkanes and cycloalkanes are insoluble in water. Water molecules are polar, and alkane and
cycloalkane molecules are nonpolar. Molecules of unlike polarity have limited solubility in
one another. The water insolubility of alkanes makes them good preservatives for metals.
Also have biological functions as protective coatings.

Alkanes and cycloalkanes have densities lower than that of water. Alkane and cycloalkane
densities fall in the range 0.6 g/mL to 0.8 g/mL, compared with waters density of 1.0 g/mL.

Branching on a carbon chain lowers the boiling point of an alkane. Branched alkanes are
more compact, with smaller surface areas than their straight-chain isomers.

Cycloalkanes have higher boiling points than their noncyclic counterparts with the same
number of carbon atoms. These differences are due in large part to cyclic systems having
more rigid and more symmetrical structures.
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Alkanes
The boiling points of the first four normal alkanes, methane through butane, are lower than
room temperature (about 25C), so at this temperature each exists as a gas. Larger normal
alkanes, pentane through heptadecane (17 carbon atoms), are liquids at room
temperature, while those larger than heptadecane are solids.

Undecane and cyclohexane are examples of two naturally occurring alkanes. Undecane is an
acyclic alkane with molecular formula C11H24. Undecane is a pheromone, a chemical
substance used for communication in a specific animal species, most commonly an insect
population. Secretion of undecane by a cockroach causes other members of the species to
aggregate.
Cyclohexane, a cycloalkane with molecular formula C6H12, is one component of the mango,
the most widely consumed fruit in the world.

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Wh e re D o We Obta i n A l kanes ?
The two major sources of alkanes are natural gas
and petroleum. Natural gas consists of
approximately 90 to 95% methane, 5 to 10%
ethane, and a mixture of other relatively low-
boiling alkaneschiefly propane, butane, and 2-
methylpropane.
Petroleum is a thick, viscous liquid mixture of
thousands of compounds, most of them
hydrocarbons, formed from the decomposition of
marine plants and animals.
petroleum, along with natural gas, provides nearly
90% of the organic raw materials for the synthesis
and manufacture of synthetic fibers, plastics,
detergents,
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Alkanes Isomerism
CH4, C2H6, and C3H8 are straight chain alkanes. But C4H10, which would be expected to be the
molecular formula of the four-carbon alkane. A new
phenomenon arises, however, when an alkane has four or more carbon atoms. There is
more than one structural formula that is consistent with the molecular formula. Consequently,
more than one compound exists with that molecular formula. This situation brings us to the
topic of isomerism.

Isomers are compounds that have the same molecular formula (that is, the same
numbers and kinds of atoms) but that differ in the way the atoms are arranged. This class of
isomerism is called constitutional isomers.

Isomers, even though they have the same molecular formula, are always different
compounds with different properties.
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n-butane

Neopentane
where n denotes normal (straight-chain) butane

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Regardless of the reason for the isomerism, constitutional isomers are always different
compounds with different properties but with the same formula.

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Alkyl Groups
Removing a hydrogen from an alkane results in an alkyl substituent (or an alkyl group).
Alkyl substituents are named by replacing the ane ending of the alkane with yl. The letter R
is used to indicate any alkyl group.

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Common names for Branched Alkyl Groups

5-C group called


neopentyl group.
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Common names for Branched Alkyl Groups

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C LASSIFICATION OF CARBON ATOMS

Each of the carbon atoms within a hydrocarbon structure can be classified as a primary,
secondary, tertiary, or quaternary carbon atom.

A primary carbon atom is a carbon atom in an organic molecule that is bonded to only one
other carbon atom.
A secondary carbon atom is a carbon atom in an organic molecule that is bonded to two
other carbon atoms.
A tertiary carbon atom is a carbon atom in an organic molecule that is bonded to
three other carbon atoms.
A quaternary carbon atom is a carbon atom in an organic molecule that is bonded
to four other carbon atoms

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C LASSIFICATION OF CARBON ATOMS

Primary carbon (1)


Secondary carbon (2)= sec
Tertiary carbon (3)= tert
Quaternary carbon (4)
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Like the carbons, the hydrogen's in a molecule are also referred to as primary, secondary,
and tertiary. Primary hydrogen's are attached to a primary carbon, secondary
hydrogen's are attached to a secondary carbon, and tertiary hydrogen's are attached to a
tertiary carbon.

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THE NOMENCLATURE OF ALKANES
Trivial or common names, such as methane, ethane, propane, and butane. After butane chemist
started to use Greek prefixes that indicate the number of carbon atoms in the molecule. Thus,
pentane contains five carbons, hexane has six, heptane has seven, and so forth.

As more compounds and isomers were discovered, however, it became increasingly difficult to
devise unique names and much more difficult to commit them to memory. Obviously,
a systematic method was needed.

The International Union of Pure and Applied Chemistry (IUPAC) has devised a set of rules that is
widely used to name organic compounds. Using the IUPAC rules to name an alkane involves
identifying the parent chain (the longest continuous chain of carbon atoms in the molecule) and
substituents (atoms or groups of atoms attached to the parent chain). In alkanes the
substituents, called alkyl groups, are constructed solely of carbon and hydrogen atoms.
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A chemical name typically has four parts in the IUPAC system of nomenclature: prefix, parent,
locant, and suffix. The prefix specifies the location and identity of various substituent groups in
the molecule, the parent selects a main part of the molecule and tells how many carbon atoms
are in that part, the locant gives the location of the primary functional group, and the suffix
identifies the primary functional group.

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To name an alkane you have to fellow these simple rules:

Step 1
Find the parent hydrocarbon.
(a) Find the longest continuous chain of carbon atoms in the molecule, and
use the name of that chain as the parent name. The longest chain may not
always be apparent from the manner of writing; you may have to turn
corners. Alkane always ends with the suffix ane.

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(b)If two different chains of equal length are present, choose the one with the
larger number of branch points as the parent:

Step 2
Number the atoms in the longest chain.
(a) Beginning at the end nearer the first branch point, number each carbon
atom in the parent chain:
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The first branch occurs at C3 in the proper system of numbering, not at C4.

(b) If there is branching an equal distance from both ends of the parent chain, begin numbering
at the end nearer the second branch point:

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Step 3
Identify and number the substituents.
(a) Assign a number (called a locant) to each substituent to locate its point of attachment to the
parent chain:

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(b) If
there are two substituents on the same carbon, give them both the same number. There
must be as many numbers in the name as there are substituents.

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Step 4
Write the name as a single word.
Use hyphens to separate the different prefixes, and use commas to separate
numbers. If two or more different substituents are present, cite them in alphabetical
order. If two or more identical substituents are present on the parent chain, use one
of the multiplier prefixes di-, tri-, tetra-, and so forth, but dont use these prefixes for
alphabetizing. Full names for some of the examples are here:

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Step 5
Name a branched substituent as though it were itself a compound.
In some particularly complex cases, a fifth step is necessary. It occasionally happens that a
substituent on the main chain is itself branched. In the following case, for instance, the
substituent at C6 is a three-carbon chain with a methyl sub-branch. To name the compound
fully, the branched substituent must first be named.

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Begin numbering the branched substituent at its point of its attachment to the main chain, and
identify it as a 2-methylpropyl group. The substituent is alphabetized according to the first
letter of its complete name, including any numerical prefix, and is set off in parentheses when
naming the entire molecule:

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More examples

Important: If a prefix such as di is part of a branch name, it is included in the


alphabetization.
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For historical
reasons, some
of the simpler
branched-chain
alkyl groups
also have
nonsystematic,
common
names, as
noted earlier.

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When writing an alkane name, the
nonhyphenated prefix iso- is considered
IUPAC name part of the alkyl-group name for alphabetizing
purposes, but the hyphenated and italicized
prefixes sec- and tert- are not. Thus, isopropyl
and isobutyl are listed alphabetically under i,
but sec-butyl and tert-butyl are listed under b.
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Draw the structure of 3-isopropyl-2-methylhexane.
Look at the parent name (hexane), and draw its carbon structure.
CCCCCC Hexane
Next, find the substituents (3-isopropyl and 2-methyl), and place them on the
proper carbons:
Finally, add hydrogen's to
complete the structure.

3-Isopropyl-2-methylhexane

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Naming New Drugs
Naming organic compounds has become big business for drug companies. The IUPAC name of
an organic compound can be long and complex. As a result, most drugs have three names:
Systematic: The systematic name follows the accepted rules of nomenclature; this is the
IUPAC name.
Generic: The generic name is the official, internationally approved name for the drug.
Trade: The trade name for a drug is assigned by the company that manufactures it. Trade
names are often catchy and easy to remember. Companies hope that the public will
continue to purchase a drug with an easily recalled trade name long after a cheaper generic
version becomes available.

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THE NOMENCLATURE OF CYCLOALKANES

Cycloalkanes are alkanes with their carbon atoms arranged in a ring. Because of the ring,
a cycloalkane has two fewer hydrogen's than an acyclic (noncyclic) alkane with the same
number of carbons. This means that the general molecular formula for a cycloalkane is
CnH2n . Cycloalkanes are named by adding the prefix cyclo to the alkane name that
signifies the number of carbons in the ring.

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THE NOMENCLATURE OF CYCLOALKANES

The rules for naming cycloalkanes resemble the rules for naming acyclic alkanes:
1. In a cycloalkane with an attached alkyl substituent, the ring is the parent hydrocarbon
unless the substituent has more carbons than the ring. In that case, the substituent
is the parent hydrocarbon and the ring is named as a substituent. There is no
need to number the position of a single substituent on a ring.
the substituent has
more
carbons than the ring

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THE NOMENCLATURE OF CYCLOALKANES

2. If the ring has two different substituents, they are listed in alphabetical order and
the number-1 position is given to the substituent listed first.

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THE NOMENCLATURE OF CYCLOALKANES

3. If there are more than two substituents on the ring, they are listed in alphabetical
order, and the substituent given the number-1 position is the one that results in a
second substituent getting as low a number as possible. If two substituents have the
same low numbers, the ring is numberedeither clockwise or counterclockwise
in the direction that gives the third substituent the lowest possible number.

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Bicycloalkanes
An alkane that contains two rings that share two carbon atoms in common is classifyed as a
bicycloalkane. The shared carbon atoms are called bridgehead carbons, and the carbon chain
connecting them is called a bridge.

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I s o m e r i s m I n C yc l o a l ka n e s

Constitutional isomers are possible for cycloalkanes that contain four or more carbon
atoms. For example, there are five cycloalkane constitutional isomers that have the formula
C5H10: one based on a five-membered ring, one based on a four-membered ring, and three
based on a three-membered ring. These isomers are

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I s o m e r i s m I n C yc l o a l ka n e s

A second type of isomerism, called stereoisomerism, is possible for some substituted


cycloalkanes. Whereas constitutional isomerism results from differences in connectivity,
stereoisomerism results from differences in configuration.

Stereoisomers are isomers that have the same molecular and structural formulas but different
orientations of atoms in space.

Several forms of stereoisomerism exist. The form associated with cycloalkanes is called cistrans
isomerism. Cistrans isomers are isomers that have the same molecular and structural formulas
but different orientations of atoms in space because of restricted rotation about bonds.

Consider the following two structures for the


molecule 1,2-dimethylcyclopentane.
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I s o m e r i s m I n C yc l o a l ka n e s
Cis- is a prefix that means on the same
side.
Trans- is a prefix that means across
from.

The presence of a substituent on each of two carbon atoms in the ring is the requirement for its
occurrence. In biochemistry, we will find that the human body often selectively distinguishes
between the cis and trans isomers of a compound. One isomer will be active in the body and
the other inactive.

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I s o m e r i s m I n C yc l o a l ka n e s
In cycloalkanes, cistrans isomerism can
also be denoted by using wedges and
dotted lines. A heavy wedge shaped
bond to a ring structure indicates a bond
above the plane of the ring, and a
broken dotted line indicates a bond
below the plane of the ring.

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I s o m e r i s m I n C yc l o a l ka n e s
The designations cis- and trans- become ambiguous in situations where either or both of the
substituted carbons have two different substituents but no hydrogen atoms.

The first structure is the cis- isomer if the focus is on H and the ethyl group; the second
structure is the trans- isomer if the focus is on H and the methyl group. A different
nomenclature system, called the E,Z nomenclature system must be used to distinguish such
isomerism.
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Sigma Bonds and Bond Rotation
Two groups bonded by only a single bond can undergo rotation about that bond
with respect to each other.
The temporary molecular shapes that result from such a rotation are called
conformations of the molecule.
Each possible structure is called a conformer.
An analysis of the energy changes that occur as a molecule undergoes
rotations about single bonds is called a conformational analysis.

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Conformations of Cyclohexane:The Chair and the Boat
The most stable conformation of cyclohexane is the chair conformation.
There is no angle or torsional strain in the chair form of cyclohexane.
In a chair conformation, all of the carboncarbon bond angles are 109.5,
and are thereby free of angle strain. The chair conformation is free of torsional
strain, as well. When viewed along any carboncarbon bond, the bonds are
seen to be perfectly staggered. Moreover, the hydrogen atoms at opposite
corners of the cyclohexane ring are maximally separated.

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Conformations of Cyclohexane:The Chair and the Boat
By partial rotations about the carboncarbon single bonds of the ring, the chair
conformation can assume another shape called the boat conformation.

The boat conformation has no angle strain, but it does have torsional strain.

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The axial bonds of cyclohexane are those that are perpendicular to the
average plane of the ring. There are three axial bonds on each face of the
cyclohexane ring, and their orientation (up or down) alternates from one
carbon to the next.
The equatorial bonds of cyclohexane are those that extend from the
perimeter of the ring. The equatorial bonds alternate from slightly up to
slightly down in their orientation from one carbon to the next.
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C h e m i c a l P ro p e r t i e s O f A l ka n e s A n d C yc l o a l ka n e s
1) Combustion:
A combustion reaction is a chemical reaction between a substance and oxygen (usually
from air) that proceeds with the evolution of heat and light (usually as a flame). Alkanes
readily undergo combustion when ignited. When sufficint oxygen is present to support
total combustion, carbon dioxide and water are the products.

2) Halogenation: Adding fluorine (F2), chlorine (Cl2), bromine (Br2), and iodine (I2). A
halogenation reaction is a chemical reaction between a substance and a halogen in which one or
more halogen atoms are incorporated into molecules of the substance. Alkane halogenation is an
example of a substitution reaction, a type of reaction that occurs often in organic chemistry.
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C h e m i c a l P ro p e r t i e s O f A l ka n e s A n d C yc l o a l ka n e s
A substitution reaction is a chemical reaction in which part of a small reacting molecule
replaces an atom or a group of atoms on a hydrocarbon or hydrocarbon derivative.

In darkness halogenation does not take place. the reaction mixture must be heated to 100C
or higher or expose it to light. The products of the reaction between methane and chlorine
are chloromethane and hydrogen chloride.

If chloromethane is allowed to react with more chlorine, further chlorination produces a


mixture of dichloromethane, trichloromethane, and tetrachloromethane.

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I m p o r ta n c e o f H a l o a l ka n e s ( A l k y l H a l i d e ) a n d A l ka n e s
An alkane mixture known as mineral oil is (C-15 to C40) sometimes used to replace
natural skin oils washed away by frequent bathing or swimming. Petroleum jelly (Vaseline
is a well-known brand name) is a semisolid mixture of alkanes that is used as both an
emollient and a protective film.

Some common uses of haloalkanes include solvents and anesthetics. General anesthetics
are compounds that are inhaled or injected to cause a loss of sensation so that surgery or
other procedures can be done without causing pain to the patient. As nonpolar
compounds, they are soluble in the nonpolar nerve membranes, where they decrease the
ability of the nerve cells to conduct the sensation of pain. Trichloromethane, commonly
called chloroform CHCl3, was once used as an anesthetic, but it is toxic and may be
carcinogenic.

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For minor surgeries, a local anesthetic such as chloroethane (ethyl chloride), CH3CH2Cl,
is applied to an area of the skin. Chloroethane evaporates quickly, cooling the skin and
causing a loss of sensation.
One of the most widely used general anesthetics is halothane (2-bromo-2-chloro-1,1,1-
trifluoroethane), also called fluothane. It has a pleasant odor, is nonexplosive, has few
side effects, undergoes few reactions within the body, and is eliminated quickly from the
body.
Liquid alkanes with 9 to 17 carbon atoms have higher boiling points
and are found in kerosene, diesel, and jet fuels. Motor oil is a
mixture of high-molecular-weight liquid hydrocarbons and is used
to lubricate the internal components of engines. Mineral oil is a
mixture of liquid hydrocarbons and is used as a laxative and a
lubricant. Alkanes with18 or more carbon atoms are waxy solids at
room temperature. Known as paraffins, they are used in waxy
coatings added to fruits and vegetables to retain moisture, inhibit
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mold, and enhance appearance.