chapter 10 introduction to organic chemistry:...
TRANSCRIPT
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Chapter 10 Introduction to
Organic Chemistry: Alkanes
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Organic Chemistry
An organic compound
• is a compound made from carbon atoms
• has one or more C atoms
• has many H atoms
• may also contain O, S, N, and halogens
• usually has carbon written first
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Organic Compounds
Typical organic compounds
• have covalent bonds
• have low melting points
• have low boiling points
• are flammable
• are soluble in nonpolar solvents
• are not soluble in water
Vegetable oil is an organic compound
and not soluble in water.
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Comparing Organic and
Inorganic Compounds
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Bonding in Organic Compounds
In organic compounds,
• carbon has 4 valence electrons and hydrogen has 1
• carbon achieves an octet by forming four bonds, with each
line representing 2 electrons
CH4, methane
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C + 4 H C HH
H
H
C HH
H
H
C
H
H
H H
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Tetrahedral Structure of Carbon CH4
VSEPR theory predicts that
a carbon atom with four
single, covalent bonds has a
tetrahedral shape.
Methane is represented
using different models:
(a) tetrahedron, (b) ball-and-
stick model, (c) space-filling
model, (d) expanded
structural formula.
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Tetrahedral Structure of Carbon C2H6
In ethane,
• each carbon forms covalent bonds to another carbon and three hydrogen atoms
• each carbon atom retains its tetrahedral shape
Ethane, CH3─CH3
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CH
H
HC
H
H
H CC H
H
H
H
H
H
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In molecules with two or more
carbon atoms, each carbon atom
with four single bonds has a
tetrahedral shape.
Representations of ethane:
(a) tetrahedral shape of each
carbon, (b) ball-and-stick
model, (c) space-filling model,
(d) expanded structural formula.
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Tetrahedral Structure of Carbon C2H6
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Learning Check
In the butane molecule, C4H10, predict the shape around each
carbon atom.
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C
H
H
H C
H
H
C
H
H
C
H
H
H
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Solution
In the butane molecule, C4H10, predict the shape around each carbon atom.
Each carbon atom has four single covalent bonds and therefore a tetrahedral shape.
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C
H
H
H C
H
H
C
H
H
C
H
H
H
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Alkanes
Alkanes are organic molecules
• containing primarily C–C single bonds
• commonly used as fuels for heaters and cooktops
• whose names end in ane
• named by using the number of carbon atoms connected in a continuous chain
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IUPAC Naming of the First Ten Alkanes
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Condensed Structural Formulas
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
• of butane, four carbon atoms are attached in a straight line
CH3CH2CH2CH3 butane
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Condensed Structural Formulas
Alkanes are written with structural formulas that are
• expanded to show each bond
• condensed to show each carbon atom and its attached hydrogen atoms
Expanded Condensed Expanded
Condensed
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C
H
H
H CH3= C
H
H
CH2=
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Writing Structural Formulas
Carbon atoms in a chain
• maintain tetrahedral shape
• are connected in a zigzag pattern
• are drawn as two-dimensional
• can be written in several conformations
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Expanded, Condensed,
and Skeletal Structures
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A hexane molecule can
be represented in several ways:
• a molecular formula
• a ball-and-stick model
• an expanded structural formula
• a condensed structural formula
• a skeletal formula
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Learning Check
Write the condensed structural formula for
A. ethane
B. heptane
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Solution
Write the condensed structural formula for
A. ethane CH3CH3
B. heptane CH3CH2CH2CH2CH2CH2CH3
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Cycloalkanes
Cycloalkanes
• are cyclic alkanes
• have two less hydrogen atoms than the open chain
• 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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H2C
H2C
CH2H3C
H2C
CH3
CnH(2n+2) CnH2n
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Formulas of Cycloalkanes
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Learning Check
Name the following alkanes:
A. CH3CH2CH2CH3
B.
C. CH3CH2CH2CH2CH2CH2CH2CH3
D.
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Solution
Name the following alkanes:
A. CH3CH2CH2CH3 butane
B. cyclopropane
C. CH3CH2CH2CH2CH2CH2CH2CH3 octane
D. cyclohexane
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Substitutions - Isomers
Isomers
• have the same molecular
formula with different atom
arrangements
• of butane (C4H10) are a straight
chain and a branched chain
The isomers of butane have the
same number and type of atoms,
but the atoms are bonded in a
different order.
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Substituents and Alkyl Groups
Substituents are atoms or groups of atoms attached to the
carbon chain and include alkyl and halo groups.
Alkyl groups are
• carbon branches attached to carbon chains
• named with a yl ending
Halo substituents are
• halogens attached to the carbon chain
• named as fluoro, chloro, bromo, or iodo
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Substituents and Alkyl Groups
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Guide to Naming Alkanes
with Substituents
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Write IUPAC Names for Alkanes
with Substituents
Give the IUPAC name for the following compound:
Step 1 Write the alkane name of the longest chain of
carbon atoms.
The longest chain has
five carbons, pentane.
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C
H
H
C
Cl
H
C
H
CH3
CH C
H
H
H
H
H
C
H
H
C
Cl
H
C
H
CH3
CH C
H
H
H
H
H
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Write IUPAC Names for Alkanes with
Substituents
Step 2 Number the carbon atoms starting from the end
nearer a substituent.
Step 3 Give the location and name of each substituent (in
alphabetical order) as a prefix to the name of the main
chain.
2-chloro-3-methylpentane
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C
H
H
C
Cl
H
C
H
CH3
CH C
H
H
H
H
H
1 2 3 4 5
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Learning Check
Give the IUPAC name for the following compound:
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C
H
Br
C
Br
H
C
CH3
H
CH
H
H
H
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Solution
Give the IUPAC name for the following compound:
Step 1 Write the alkane name of the longest chain of
carbon atoms.
The longest chain has
four carbons, butane.
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C
H
Br
C
Br
H
C
CH3
H
CH
H
H
H
C
H
Br
C
Br
H
C
CH3
H
CH
H
H
H
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Solution
Step 2 Number the carbon atoms starting from the end
nearer a substituent.
Step 3 Give the location and name of each substituent (in
alphabetical order) as a prefix to the name of the main
chain.
1,2-dibromo-3-methylbutane
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C
H
Br
C
Br
H
C
CH3
H
CH
H
H
H1 2 3 4
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Naming Cycloalkanes with Substituents
Give the IUPAC name for the following cycloalkane.
Step 1 Write the alkane name of the longest chain
of carbon atoms.
The longest chain is a
six-member ring, cyclohexane.
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CH2CH3
C
C
C
C
C
C CH2CH3
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Solution
Step 2 Number the carbon
atoms starting from the end
nearer a substituent.
Step 3 Give the location and name of each substituent (in
alphabetical order) as a prefix to the name of the main
chain.
For cycloalkanes with just one substituent, there is no need
to give the location of the substituent:
ethylcyclohexane
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C
C
C
C
C
C CH2CH3
1
23
4
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Drawing Formulas for Alkanes
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Draw the structure for 1-chloro-1,2-dimethylheptane
heptane – 7-carbon chain
methyl group on carbon 1 and 2
chlorine on carbon 1
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Guide to Drawing Formulas for Alkanes
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Learning Check
Draw the condensed structural formula for
3-bromo-1-chlorobutane.
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Solution
Draw the condensed structural formula for
3-bromo-1-chlorobutane.
Step 1 Draw the main chain of carbon atoms.
The longest chain in butane has four carbon atoms. CCCC
Step 2 Number chain and place the substituents on the carbons indicated by the numbers. 1 2 3 4
3-bromo: Br goes on carbon 3. CCCC Cl Br 1-chloro: Cl goes on carbon 1.
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Cl
Br
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Solution
Draw the condensed structural formula for
3-bromo-1-chlorobutane.
Step 3 Add hydrogen to complete four bonds to each carbon.
CH2CH2CHCH3
Cl Br 3-bromo-1-chlorobutane
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Cl
Br
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Learning Check
Name each of the following cycloalkanes.
A.
B.
C.
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CH3
Cl
H2C
CH3
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Solution
Name each of the following cycloalkanes.
A. methylcyclopropane
B. ethylcyclobutane
C. chlorocyclopentane
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CH3
Cl
H2C
CH3
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Some Uses of Alkanes 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 highly volatile liquids at room temperature, making them useful in fuels such as gasoline.
pentane, hexane, heptane, octane
Octane has eight carbons:
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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 carbons
• have high molar masses
• are waxy solids at room temperature
• are used in waxy coatings of fruits and vegetables
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Solubility and Density of Alkanes
Alkanes are
• nonpolar
• insoluble in water
• less dense than water
• flammable in air
The crude oil in oil spills floats on top of the water,
forming a thin layer on the surface because it is less dense
than water.
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Combustion of Alkanes
Alkanes
• have strong CC bonds
• react with oxygen gas to make carbon dioxide and
water in combustion reactions
• release energy when CC bonds are broken in
combustion reactions
CH4(g) + 2O2(g) CO2(g) + 2H2O(g) + energy
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Learning Check
Propane is a fuel often used in barbeques. Write a balanced
equation for the complete combustion of propane.
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Solution
Unbalanced equation:
C3H8 + O2 CO2 + H2O
Balance C:
C3H8 + O2 3CO2 + H2O
Balance H:
C3H8 + O2 3CO2 + 4H2O
Balance O:
C3H8 + 5O2 3CO2 + 4H2O (balanced)
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Elements in Organic Compounds
In organic molecules, carbon atoms bond
• with four bonds
• mostly with H and other C atoms
• sometimes to O, N, S
• sometimes to halogens F, Cl, and Br
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Functional Groups
Functional groups are
• a characteristic feature of organic molecules that behave in a predictable way
• composed of an atom or group of atoms
• groups that replace a hydrogen atom in the corresponding alkane
• a way to classify families of organic compounds
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Alkenes, Alkynes, and Aromatic Compounds
Alkenes contain a double bond between adjacent carbon atoms.
Alkynes contain a triple bond.
Aromatic compounds contain a ring of six carbon atoms
called benzene.
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Comparing Alkenes, Alkynes, and Aromatic
Compounds
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Learning Check
50
Identify the following compounds as an alkene, alkyne, or
aromatic compound.
A.
B.
C.
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Solution
51
Identify the following compounds as an alkene, alkyne or
aromatic compound.
A. aromatic
B. alkene
C. alkyne
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Alcohols, Thiols, and Ethers
An alcohol contains the hydroxyl (−OH) functional group.
A thiol contains the thiol (−SH) functional group.
An ether contains an oxygen atom bonded to two carbon atoms (COC) functional group.
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Aldehydes and Ketones
An aldehyde contains a carbonyl
group (C=O), which is a carbon atom
with a double bond to an oxygen atom.
The carbonyl carbon is attached to a
hydrogen.
In a ketone, the carbon
of the carbonyl group (C=O) is
attached to two carbon atoms.
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C
H
O
C
C
C
O
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Carboxylic Acids and Esters
Carboxylic acids contain the
carboxyl group, which is a
carbonyl group attached
to a hydroxyl group.
COOH
An ester contains the
carboxyl group between
carbon atoms.
COOCH3
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C
C
OH
O
C
C
O
O
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Amines
Amines
• have a functional group that
contains a nitrogen atom
• are derivatives of ammonia,
NH3, in which one, two, or
three hydrogen atoms are
replaced with carbons
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H3C N
H
H
H3C N
CH3
H
H3C N
CH3
CH3
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Amides
Amides
• have an amine group instead
of an OH group on the
carbonyl carbon
• are an important biological
functional group, the
simplest amide
being urea
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C
N
O
H2N
C
O
NH2
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Classification of Organic Compounds
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Learning Check
Classify each of the following as an alcohol, ether,
aldehyde, ketone, carboxylic acid, ester, amine, or amide.
A.
B.
C.
D.
E.
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Solution
Classify each of the following as an alcohol, ether,
aldehyde, ketone, carboxylic acid, ester, amine, or amide.
A.
B.
C.
D.
E.
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alcohol
ether
amine
carboxylic acid
ester
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Concept Map – Organic Compounds
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