Introduction to Organic Chemistry: Hydrocarbons
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kimoda freelancerIntroduction to Organic Chemistry: Hydrocarbons
Uploaded by
kimoda freelancerChemistry: An Introduction to General,
Organic, and Biological Chemistry
Thirteenth Edition
Chapter 11
Introduction to Organic
Chemistry: Hydrocarbons
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11.1 Organic Compounds
Organic chemistry is the study of carbon compounds.
An organic compound
• is a compound made from carbon and hydrogen atoms
• may also contain other non-metals such as oxygen, sulfur,
nitrogen, phosphorus, or a halogen
• is often found in common products such as gasoline,
medicines, shampoos, plastics, and perfumes
Learning Goal Identify properties characteristic of
organic or inorganic compounds.
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Organic Compounds
Organic molecules are found in biological systems.
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Organic Compounds
They can be synthetic or natural.
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Properties of Organic Compounds
Organic compounds typically
• have covalent bonds
• have low melting and boiling
points
• are flammable and undergo
combustion
• are not soluble in water
Vegetable oil is a mixture of organic compounds and is not
soluble in water.
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Hydrocarbons
• Hydrocarbons are organic compounds that contain only
carbon and hydrogen.
• In organic molecules, every carbon has four bonds.
• Saturated hydrocarbons contain only single bonds.
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Carbon Compounds: Methane C(CH 4 4)
H sub
In methane, CH4 , carbon forms four covalent bonds to
hydrogen. Methane is tetrahedral and has bond angles of
109 °.
Two-dimensional and three-dimensional representations of
methane, CH4 :
a. space-filling model d. expanded structural formula
b. ball-and-stick model e. condensed structural formula
c. wedge-dash model
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Carbon Compounds: Ethane (C2H6 ) C sub 2 H sub 6
In ethane, C2H6 , each tetrahedral carbon forms three
covalent bonds to hydrogen and one to the other carbon.
Two-dimensional and three-dimensional representations of
methane, C2H6 :
a. space-filling model d. expanded structural formula
b. ball-and-stick model e. condensed structural formula
c. wedge-dash model
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11.2 Alkanes
A large number of carbon
compounds are possible
because the covalent bond
between carbon atoms, such
as those in hexane, C6H14 ,
are very strong.
Learning Goal Names and draw the condensed and line-
angle formulas for alkanes and cycloalkanes.
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Naming Alkanes
Alkanes
• are hydrocarbons that contain only
C -- C and C -- H bonds
• are formed by a continuous chain of carbon atoms
• are named using the IUPAC (International Union of Pure
and Applied Chemistry) system
• have names that end in ane
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Condensed Structural Formulas (1of 2)
Alkanes are written with structural formulas that are
• expanded to show each bond
• condensed to show each carbon atom and its attached
hydrogen atoms
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Condensed Structural Formulas (2 of 2)
In a condensed structural formula,
• each carbon atom and its attached hydrogen atoms are
written as a group
• a subscript indicates the number of hydrogen atoms
bonded to each carbon atom
The condensed structural formula of butane has four carbon
atoms.
CH3 -- CH2 -- CH2 -- CH3 butane
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Line-Angle Formulas
Alkane compounds can also be represented by
• line-angle formulas, which show the carbon skeleton in
which carbon atoms are represented at the end of each
line or at each corner
CH3 -- CH2 -- CH2 -- CH3 butane
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Conformations of Alkanes
Single bonds, in general, rotate freely.
• Alkanes can exist in different arrangements called
conformations, occur during rotation about a single bond.
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Alkane Representations
An alkane molecule can be represented in several ways:
• as a molecular formula
• as a ball-and-stick model
• as an expanded structural formula
• as a condensed structural formula
• as a line-angle formula
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Structural Formulas for Butane, C4H10 C sub 4 H sub 10
Table 11.3 Some Structural Formulas for Butane, C4H10
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IUPAC Naming of First Ten Alkanes
Table 11.2 IUPAC Names and Formulas of the First Ten Alkanes
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Cycloalkanes
Cycloalkanes
• are cyclic alkanes
• have two fewer hydrogen atoms than the open chain form
• are named by using the prefix cyclo before the name of
the alkane chain with the same number of carbon atoms
propane, C3H8 cyclopropane, C3H6
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Formulas of Cycloalkanes
Table 11.4 Formulas of Some Common Cycloalkanes
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Learning Check 1
Give the IUPAC name for each of the following compounds:
A.
B.
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Solution 1
Give the IUPAC name for each of the following compounds:
A.
An alkane with eight continuous carbon atoms is octane.
B.
A cyclic molecule with five carbon atoms is
cyclopentane.
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11.3 Alkanes with Substituents
When an alkane has four or
more carbon atoms, the
atoms can be arranged so
that a side group called a
branch or substituent is
attached to a carbon chain.
Learning Goal Name alkanes with substituents and draw
their condensed structural or line-angle formulas.
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Structural Isomers
Structural isomers
• have the same molecular
formula with a different
connectivity of atoms
• have the same number of
atoms bonded in a different
order
Butane, C4H10 , has two structural isomers: a straight chain
and a branched chain.
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Structural Isomers
Three possible structural isomers of pentane, C5H12 .
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Alkane Substituents
Substituents are atoms or groups of atoms attached to the
carbon chain and include alkyl and halo groups.
Alkyl groups are
• groups of carbon atoms attached to carbon chains
• named in the IUPAC system with an yl ending
Halo substituents are
• halogen atoms attached to the carbon chain
• named in the IUPAC system as fluoro, chloro, bromo, or
iodo.
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Substituents and Alkyl Groups
Table 11.5 Formulas and Names of Some Common
Substituents
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Name Alkanes with Substituents (1 of 2)
Step 1: Write the alkane name for the longest chain of
carbon atoms.
The longest chain has five carbons—pentane.
Step 2: Number the carbon atoms from the end nearer to a
substituent.
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Name Alkanes with Substituents (2 of 2)
Step 3: Give the location and name for each substituent
(alphabetical order) as a prefix to the name of the
main chain.
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Naming Cycloalkanes with Substituents
When one substituent is attached to a carbon atom in a
cycloalkane,
• the name of the substituent is placed in front of the
cycloalkane name
• no number is needed for a single alkyl group or halogen
atom
The IUPAC name for the following
cycloalkane is ethylcyclohexane.
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Drawing Formulas for Alkanes
The IUPAC name gives all the information needed to draw
the condensed structural formula for an alkane.
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Learning Check 2
Draw the condensed structural and line-angle formula for
3-bromo-1-chlorobutane.
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Solution 2
Draw the condensed structural and line-angle formula for
3-bromo-1-chlorobutane.
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Learning Check 3
Name each of the following alkanes:
A.
B.
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Solution 3
Name each of the following alkanes:
A. 2-chloropentane
B. 2,3-dimethylpentane
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11.4 Properties of Alkanes
The different uses of alkane
compounds result from their
physical properties, including
their solubility and density.
The solid alkanes that make
up waxy coatings on fruits
and vegetables help retain
moisture, inhibit mold, and
enhance appearance.
Learning Goal Identify the properties of alkanes and write a
balanced chemical equation for combustion.
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Uses of Alkanes (1 of 2)
Alkanes with one to four carbons are gases at room
temperature and are widely used as heating fuels.
methane, ethane, propane, butane
Butane has four carbons:
Alkanes with five to eight carbons are volatile liquids, found
in gasoline.
pentane, hexane, heptane, octane
Octane has eight carbons:
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Uses of Alkanes (2 of 2)
Alkanes with 9−17 carbons are liquids with higher boiling
points and are found in motor oils, mineral oil, kerosene,
diesel, and jet fuels.
Decane has 10 carbons:
• Alkanes with 18 or more carbon atoms, known as
paraffins, are waxy solids at room temperature.
• Petroleum jelly, or Vaseline, is a semisolid mixture of
hydrocarbons, with more than 25 carbon atoms.
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Solubility and Density of Alkanes
Alkanes are
• nonpolar
• insoluble in water
• less dense than water
• flammable in air
• found in crude oil
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Combustion of Alkanes
Alkanes with strong C -- C bonds
• react with oxygen gas to make carbon dioxide and water in
combustion reactions
• release energy when C -- C bonds are broken in combustion
reactions
CH4 ( g ) + 2O2 ( g ) ¾¾
D
® CO2 ( g ) + 2H2O ( g ) + energy
Methane is the natural gas used to cook our food on gas
cooktops and to heat our homes.
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Combustion of Butane
Butane
• is used in portable burners
• undergoes combustion and
produces enough energy to
cook food
2C4H10 ( g ) + 13O2 ( g ) ¾¾
D
® 8CO2 ( g ) + 10H2O ( g ) + energy
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11.5 Alkenes and Alkynes
Alkenes and alkynes are families of hydrocarbons that
• contain double and triple bonds, respectively
• are called unsaturated hydrocarbons because they do not
contain the maximum number of hydrogen atoms
• react with hydrogen gas to increase the number of
hydrogen atoms and become alkanes
Learning Goal Provide IUPAC name and draw the
condensed structural or line-angle formulas for alkenes and
alkynes.
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Identifying Alkenes
Alkenes contain one or more carbon–
carbon double bonds.
In ethene, C2H4 , two carbon atoms
are connected by a double bond.
Each carbon atom in the double bond is
attached to two hydrogen atoms and
has a trigonal planar arrangement with
bond angles of 120°.
Ethene (aka ethylene) is an important plant hormone in
promoting the ripening of fruit such as bananas. It
accelerates the breakdown of cellulose in plants, which
causes flowers to wilt and leaves to fall from trees.
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Identifying Alkynes
Alkynes contain one or more carbon–
carbon triple bonds.
In ethyne, C2H2,
• two carbon atoms are connected by a
triple bond
• each carbon is also bonded to one H
atom
Each carbon atom in the triple bond has a linear
arrangement with bond angles of 180°.
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Naming Alkenes, and Alkynes
The IUPAC names for alkenes and alkynes
• are similar to those of alkanes
• use the alkane name with the same number of carbon atoms,
replacing the ane ending with ene for alkene, and yne for alkyne.
Cyclic alkenes are named as cycloalkenes.
Table 11.6 Comparison of Names for Alkanes, Alkenes, and Alkynes
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Learning Check 4
Write IUPAC names for each of the following:
A.
B.
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Solution 4 (1 of 3)
Step 1: Name the longest carbon chain that contains the
double or triple bond.
A.
five carbon atoms—pentene
B.
six carbon atoms—hexyne
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Solution 4 (2 of 3)
Step 2: Number the carbon chain starting from the end
nearer the double or triple bond.
A. 2-pentene
B. 2-hexyne
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Solution 4 (3 of 3)
Step 3: Give the location and name of each substituent
(alphabetical order) as a prefix to the alkene or alkyne name.
A. 4-methyl-2-pentene
B. 2-hexyne; there are no
substituents in this compound.
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Naming Cycloalkenes
Cycloalkenes have a double bond within a ring structure and
• are named by assigning the double bond to be between
carbon 1 and carbon 2 when a substituent is on the ring
• do not need to include the numbers for the double bond
3-methylcyclopentene (It is
understood the double bond is
between carbon 1 and carbon 2.)
The carbon atoms in the ring are numbered to give the
double bond numbers 1 and 2, then the lowest possible
number to any substituents present.
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Learning Check 5
Name the following alkenes and alkynes:
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Solution 5
Name the following alkenes and alkynes:
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11.6 Cis–Trans Isomers
The atoms or groups of atoms
attached to the carbon atoms
on the double bond may form
two different structures, which
are called geometric or cis–
trans isomers.
Cis–trans isomers have
different physical and chemical
properties.
Learning Goal Draw the condensed structural formulas and
give the names for the cis–trans isomers of alkenes.
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Cis–Trans Isomers
In an alkene, the double bond
• is rigid and does not rotate
• holds attached groups in fixed positions
• makes cis–trans isomers possible when two different
groups are attached to the carbon atoms on each side of
the double bond
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Cis–Trans Isomers of Butene
• In a cis isomer, the alkyl groups are
attached on the same side of the
double bond and H atoms are on the
other side.
• In a trans isomer, the alkyl groups
and H atoms are attached on
opposite sides of the double bond.
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Naming Cis–Trans Isomers
The prefix of cis or trans is placed in front of the alkene
name when the compound is a cis or trans isomer.
cis-1,2-dibromoethene trans-1,2-dibromoethene
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11.7 Addition Reactions
In alkenes and alkynes, the double and triple bonds are
• very reactive, adding H -- H and H -- OH to the carbons
in the double or triple bond
• easily broken, providing electrons to form new bonds
Table 11.7 Summary of Addition Reactions
Name of Addition Reaction Reactants Catalysts Product
Alkene+Hsub2
Hydrogenation Alkene + H2 Pt, Ni, or Pd Alkane
H+ (strong acid)
Alkene + H sub 2 O H super plus
Hydration Alkene + H2O Alcohol
Learning Goal: Predict products from addition reactions of
alkenes.
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Hydrogenation
In hydrogenation,
• hydrogen atoms add to the carbon atoms of a double
bond or triple bond
• a catalyst such as Pt, Ni, or Pd is used to speed up the
reaction
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Hydrogenation of Oils
Adding H2 to double bonds in
vegetable oils produces
• compounds with higher
melting points
• solids at room temperature,
such as margarine, soft
margarine, and shortening
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Hydration
In hydration, an alkene reacts with water, H -- OH,
to form an alcohol, and
• a hydrogen atom (H -- ) from water forms a bond with the
carbon atom in the double bond with more hydrogen atoms
• the -- OH from water forms a bond with the second carbon
atom in the double bond with fewer hydrogen atoms
• is catalyzed by a strong acid such as H2SO4
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Learning Check 6
Predict the product of the addition of H -- OH to the
following alkene:
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Solution 6
Predict the product of the addition of H -- OH to the
following alkene:
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11.8 Aromatic Compounds
In 1825, Michael Faraday
isolated a hydrocarbon
called benzene, which
consists of a six-carbon
ring with alternating double
bonds and has the
molecular formula C6H6 .
Learning Goal Describe the bonding in benzene; name
aromatic compounds and draw their line-angle formulas.
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Aromatic Compounds
Benzene is
• an aromatic compound
• a ring of six C atoms, each bonded to one H atom
• a flat ring structure drawn with three alternating double bonds
• represented by two structures because the electrons are shared
equally among all the C atoms
• represented by a skeletal formula using a circle in the center
instead of the alternating double bonds
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Naming Aromatic Compounds (1 of 3)
Aromatic compounds containing a benzene ring and a single
substituent are named as benzene derivatives. Since the
ring contains only one substituent, the ring is not numbered.
Some common names such as toluene, aniline, and phenol
are allowed by IUPAC rules.
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Naming Aromatic Compounds (2 of 3)
When there are two or more substituents, the benzene ring
is numbered to give the lowest numbers to the substituents.
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Naming Aromatic Compounds (3 of 3)
When toluene, phenol, or aniline has substituents,
• the carbon atom attached to the methyl, hydroxyl, or amine
group is numbered as carbon 1
• the other substituents are named alphabetically
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Identify Aromatics in More Complexed 67
Structures
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