Transcript cmc chapter 22

Substituted Hydrocarbons and
Their Reactions
Section 22.1 Alkyl Halides and
Aryl Halides
Section 22.2 Alcohols, Ethers,
and Amines
Section 22.3 Carbonyl Compounds
Section 22.4 Other Reactions of
Organic Compounds
Section 22.5 Polymers
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Section 22.1 Alkyl Halides and Aryl Halides
• Define functional group,
and give examples.
• Compare and contrast
alkyl and aryl halide
structures.
• Evaluate the boiling
points of organic halides.
aliphatic compound: a
nonaromatic
hydrocarbon, such as an
alkane, an alkene, or an
alkyne
Section 22.1 Alkyl Halides and Aryl Halides
(cont.)
functional group
plastic
halocarbon
substitution reaction
alkyl halide
halogenation
aryl halide
A halogen atom can replace a
hydrogen atom in some hydrocarbons.
Functional Groups
• In an organic molecule, a functional
group is an atom or group of atoms that
always reacts in a certain way.
• Addition of a functional group to a
hydrocarbon always produces a substance
with different chemical and physical
properties.
• Double and triple bonds between carbon
atoms are considered functional groups.
Functional Groups (cont.)
Organic Compounds Containing Halogens
• Any organic compound that contains a
halogen substituent is called a halocarbon.
• An alkyl halide is an organic compound
containing a halogen atom covalently bonded
to an aliphatic carbon atom.
• An aryl halide is an organic compound
containing a halogen bonded to an aromatic
group.
Organic Compounds Containing Halogens
(cont.)
• In naming halocarbons, a
prefix indicates which
halogen is present.
• If there is more than a
single halogen, they are
listed alphabetically.
Organic Compounds Containing Halogens
(cont.)
• Halocarbons have higher boiling points
because they have an increasing tendency
to form temporary dipoles.
• Dipoles attract each other, and require more
energy to separate.
• A plastic is a polymer that can be heated and
molded while relatively soft.
Organic Compounds Containing Halogens
(cont.)
Substitution Reactions
• Nearly all synthetic organic compounds
begin with petroleum.
• A substitution reaction is one in which one
atom or a group of atoms in a molecule is
replaced by another atom or group of atoms
• Hydrogen atoms in an alkane can be
replaced by atoms of halogens in a process
called halogenation.
Substitution Reactions (cont.)
Substitution Reactions (cont.)
• Once halogenated, alkanes can undergo
further reactions.
• Reacting an alkyl halide with a basic solution
results in replacement of the halogen atom
with an –OH group to form an alcohol.
Section 22.1 Assessment
Which of the following is NOT an alkyl
halide?
A. 2-fluorobutane
B. 1,3-dichlorobenzene
D
A
0%
C
D. bromoethane
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. sodium chloride
Section 22.1 Assessment
An alkane with one or more halogen
substituents is called what?
A. aryl halide
B. metal halide
D
A
0%
C
D. alkyl halide
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. chlorofluorocarbon
Section 22.2 Alcohols, Ethers, and Amines
• Identify the functional
groups that characterize
alcohols, ethers, and
amines.
• Draw the structures of
alcohols, ethers, and
amines.
• Discuss the properties
and uses of alcohols,
ethers, and amines.
miscible: describes two
liquids that are soluble
in each other
Section 22.2 Alcohols, Ethers, and Amines
(cont.)
hydroxyl group
alcohol
denatured alcohol
ether
amine
Oxygen and nitrogen are two of the
most-common atoms found in organic
functional groups.
Alcohols
• Oxygen commonly forms two covalent
bonds to form a stable octet.
• An oxygen-hydrogen group covalently
bonded to a carbon atom is called a hydroxyl
group.
• An organic compound in which a hydroxyl
group replaces a hydrogen is called an
alcohol.
Alcohols (cont.)
Alcohols (cont.)
• Alcohol is polar and mixes
completely with water.
• Denatured alcohol is ethanol
with small amounts of noxious
materials added to it.
• Alcohol names are based on
the alkane names, with the
ending –ol.
Ethers
• An ether is an organic compound
containing an oxygen bonded to two
carbon atoms.
Ethers (cont.)
• Ethers have no hydrogen atoms bonded to
their oxygen atoms, so they cannot form
hydrogen bonds with each other.
• Ethers are volatile and have low boiling
points.
• Ethers with identical chains are named by the
chain followed by the word ether.
• Ethers with different chains are named in
alphabetical order followed by ether.
Amines
• Amines contain nitrogen
atoms bonded to carbon
atoms in aliphatic chains
or aromatic rings.
Amines (cont.)
• Amines are primary, secondary, or tertiary
depending on if there are one, two, or three
hydrogen atoms replaced by organic
groups.
• Amines have the suffix –amine.
Section 22.2 Assessment
Which of the following is an alcohol?
A. cyclohexamine
B. 1-chlorobutanol
C. bromobutene
D
C
A
0%
B
D. butylpropyl ether
A. A
B. B
C. C
0%
0%
0%
D. D
Section 22.2 Assessment
Which functional group is present in an
alcohol?
A. hydroxyl group
B. halogen
D
A
0%
C
D. amino group
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. aromatic ring
Section 22.3 Carbonyl Compounds
• Identify the structures of
carbonyl compounds,
including aldehydes,
ketones, carboxylic
acids, esters, and
amides.
• Discuss the properties
of compounds containing
the carbonyl group.
electronegative:
indicates the relative
ability of an element’s
atoms to attract
electrons in a chemical
bond
Section 22.3 Carbonyl Compounds (cont.)
carbonyl group
carboxyl group
aldehyde
ester
ketone
amide
carboxylic acid
condensation reaction
Carbonyl compounds contain a doublebonded oxygen in the functional group.
Organic Compounds Containing the
Carbonyl Group
• An oxygen atom double-bonded to a
carbon atom is a carbonyl group.
• Aldehydes are organic compounds in which
the carbonyl group is located at the end of the
carbon chain and is bonded to a carbon atom
on one side and a hydrogen on the other
side.
• Aldehydes are named with the suffix –al.
Organic Compounds Containing the
Carbonyl Group (cont.)
Organic Compounds Containing the
Carbonyl Group (cont.)
• A ketone is an organic compound in which
the carbon of the carbonyl group is bonded
to two other carbon atoms.
• Ketones are named by changing the –e at the
end of the alkane name to –one, and
including a number before the name to
indicate the position of the ketone group.
• Ketones and aldehydes share many chemical
and physical properties because their
structures are similar.
Organic Compounds Containing the
Carbonyl Group (cont.)
• Ketones are popular solvents for
moderately polar substances.
• Ketones are somewhat soluble in water.
Organic Compounds Containing the
Carbonyl Group (cont.)
Carboxylic Acids
• Carboxylic acids are organic compounds
that have a carboxyl group.
• Carboxyl groups are carbonyls bonded to a
hydroxyl group
• Carboxylic acids are named by changing the
–ane to –anoic acid.
Carboxylic Acids (cont.)
Carboxylic Acids (cont.)
• Carboxylic groups are represented by
–COOH.
• Carboxylic acids are polar and reactive, and
ionize in water to form acids.
Organic Compounds Derived from
Carboxylic Acids
• An ester is any organic compound with a
carboxyl group in which the hydrogen in
the hydroxyl group is replaced by an alkyl
chain.
Organic Compounds Derived from
Carboxylic Acids (cont.)
• To name an ester, write the alkyl group
followed by the name of the acid with the
–oic acid ending replaced with –oate.
• Esters are polar molecules and many are
volatile and sweet smelling.
• Many esters are found in fruits and flowers.
Organic Compounds Derived from
Carboxylic Acids (cont.)
• An amide group is an organic compound
in which the –OH group of a carboxylic acid
is replaced by a nitrogen atom bonded to
other atoms.
Organic Compounds Derived from
Carboxylic Acids (cont.)
• The amide functional group is found
repeated many times in natural proteins
and some synthetic materials.
Condensation Reactions
• In a condensation reaction, two smaller
organic molecules combine to form a more
complex molecule, accompanied by the
loss of a small molecule such as water.
• Condensation reactions are elimination
reactions that form bonds between two atoms
not previously bonded.
Section 22.3 Assessment
Which of the following is the carbonyl
group?
A. COOH
B. C=O
D
A
0%
C
D. R-O-R′
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. CONH2
Section 22.3 Assessment
Which of the following does NOT contain
a carbonyl group?
A. ketones
B. esters
D
A
0%
C
D. aldehydes
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. amines
Section 22.4 Other Reactions of Organic
Compounds
• Classify an organic reaction into one of five
categories: substitution, addition, elimination,
oxidation-reduction, or condensation.
• Use structural formulas to write equations for
reactions of organic compounds.
• Predict the products of common types of organic
reactions.
catalyst: a substance that increases the rate of a
chemical reaction by lowering activation energies
but is not consumed in the reaction
Section 22.4 Other Reactions of Organic
Compounds (cont.)
elimination reaction
addition reaction
dehydrogenation reaction
hydration reaction
dehydration reaction
hydrogenation reaction
Classifying the chemical reactions of
organic compounds makes predicting
products of reactions much easier.
Classifying Reactions of Organic Substances
• Using combinations of reactions allows
chemical industries to convert simple
molecules from petroleum and natural gas
into large, complex organic molecules.
Classifying Reactions of Organic Substances
(cont.)
• The formation of alkenes from alkanes is
an elimination reaction, a reaction in
which a combination of atoms is removed
from two adjacent atoms forming an
additional bond between the two carbon
atoms.
Classifying Reactions of Organic Substances
(cont.)
• A reaction that eliminates two hydrogen
atoms is called a dehydrogenation
reaction.
Classifying Reactions of Organic Substances
(cont.)
• An elimination reaction in which the atoms
removed form water is called a
dehydration reaction.
Classifying Reactions of Organic Substances
(cont.)
• Addition reactions result when other
atoms bond to two atoms bonded by a
double or triple covalent bonds.
• A hydration reaction is an addition reaction
in which a hydrogen atom and hydroxyl group
from a water molecule add to a double or
triple bond.
Classifying Reactions of Organic Substances
(cont.)
• A hydrogenation reaction involves the
addition of hydrogen to atoms in a double
or triple bond.
• Catalysts are usually needed in
hydrogenation reactions.
• Hydrogenation reactions are commonly used
to convert liquid unsaturated fats into
saturated fats that are solid at room
temperature.
Classifying Reactions of Organic Substances
(cont.)
Classifying Reactions of Organic Substances
(cont.)
• Many organic compounds can be
converted to other compounds by
oxidation-reduction reactions.
Classifying Reactions of Organic Substances
(cont.)
Predicting Products of Organic Reactions
• Each type of reaction—substitution,
addition, elimination, oxidation-reduction,
and condensation—can be used to predict
the products of other organic reactions of
the same types.
Section 22.4 Assessment
Which type of reaction normally produces
an alcohol from an alkene?
A. substitution
B. elimination
D
A
0%
C
D. addition
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. hydration
Section 22.4 Assessment
What type of reaction is the following?
alkyl halide → alkene
A. halogenation
B. elimination
D
A
0%
C
D. substitution
B
C. addition
A. A
B. B
C. C
0%
0%
0%
D. D
Section 22.5 Polymers
• Diagram the relationship
between a polymer and
the monomers from
which it forms.
• Classify polymerization
reactions as addition or
condensation.
• Predict polymer
properties based on their
molecular structures and
the presence of
functional groups.
molecular mass: the
mass of one molecule of
a substance
Section 22.5 Polymers
polymer
(cont.)
monomer
condensation
polymerization
polymerization reaction
thermoplastic
addition polymerization
thermosetting
Synthetic polymers are large organic
molecules made up of repeating units
that are linked together by addition or
condensation reactions.
The Age of Polymers
• Polymers are large molecules consisting
of many repeating structural units.
• The turn of the 20th century saw the advent
of such polymers as rubber and celluloid.
Reactions Used to Make Polymers
(cont.)
• A monomer is a molecule from which a
polymer is made.
• A reaction in which monomer units are
bonded together to form a polymer are called
polymerization reactions.
• In addition polymerization all of the atoms
present in the monomers are retained in the
polymer product.
Reactions Used to Make Polymers
(cont.)
Reactions Used to Make Polymers
(cont.)
Reactions Used to Make Polymers
(cont.)
Reactions Used to Make Polymers
(cont.)
• Condensation polymerization takes
place when monomers containing at least
two functional groups combine with the
loss of a small by-product, usually water.
Properties and Recycling of Polymers
• Polymers are inexpensive and easy to
make.
• Polymers have a wide range of properties.
• They are easy to mold into different shapes.
• Thermoplastic polymers can be melted and
molded repeatedly into shapes that are
retained when cooled.
• Thermosetting polymers can be molded
when first prepared, but cannot be remelted.
Properties and Recycling of Polymers
• As fossil fuel supplies are depleted,
recycling polymers becomes more
important.
(cont.)
Section 22.5 Assessment
The smaller, repeating units that make up
a polymer are called ____.
A. structural units
B. polyunits
D
A
0%
C
D. building blocks
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. monomers
Section 22.5 Assessment
One way polymers are synthesized is
through ____ reactions.
A. condensation
B. elimination
D
A
0%
C
D. dehydration
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. substitution
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Section 22.1 Alkyl Halides and
Aryl Halides
Key Concepts
• The substitution of functional groups for hydrogen in
hydrocarbons creates a wide variety of organic
compounds.
• An alkyl halide is an organic compound that has one or
more halogen atoms bonded to a carbon atom in an
aliphatic compound.
Section 22.2 Alcohols, Ethers,
and Amines
Key Concepts
• Alcohols, ethers, and amines are formed when specific
functional groups substitute for hydrogen in
hydrocarbons.
• Because they readily form hydrogen bonds, alcohols
have higher boiling points and higher water solubilities
than other organic compounds.
Section 22.3 Carbonyl Compounds
Key Concepts
• Carbonyl compounds are organic compounds that
contain the C=O group.
• Five important classes of organic compounds
containing carbonyl compounds are aldehydes,
ketones, carboxylic acids, esters, and amides.
Section 22.4 Other Reactions of
Organic Compounds
Key Concepts
• Most reactions of organic compounds can be
classified into one of five categories: substitution,
elimination, addition, oxidation-reduction, and
condensation.
• Knowing the types of organic compounds reacting can
enable you to predict the reaction products.
Section 22.5 Polymers
Key Concepts
• Polymers are large molecules formed by combining
smaller molecules called monomers.
• Polymers are synthesized through addition or
condensation reactions.
• The functional groups present in polymers can be used
to predict polymer properties.
Aryl halides contain what two groups?
A. nitrogen and aliphatic
hydrocarbon chain
D
0%
A
D. halogen and aliphatic
hydrocarbon chain
C
C. halogen and aromatic
hydrocarbon ring
A. A
B. B
C. C
0%
0%
0%
D. D
B
B. nitrogen and aromatic
hydrocarbon ring
Amines contain which function group?
A. –OH
B. –Br
C. R-O-R′
D
C
A
0%
B
D. –NH2
A. A
B. B
C. C
0%
0%
0%
D. D
Which of the following does NOT contain
the carbonyl group?
A. ketones
B. ethers
D
A
0%
C
D. amides
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. aldehydes
What is an addition reaction in which a
hydrogen atom and hydroxyl group from a
water molecule add to a double or triple
bond called?
A. elimination reaction
A
0%
D
D. hydrogenation reaction
C
C. dehydration reaction
A. A
B. B
C. C
0%
0%
0%
D. D
B
B. hydration reaction
A type of plastic that can be molded only
when first produced is called a ____.
A. thermoplastic
B. polythermal
D
A
0%
C
D. thermosetting
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. setting plastic
What are the products of this reaction?
CH3CH2Br + NaOH → ____
A. CH3CH2Na + BrOH
A
0%
D
D. CH3CH3 + Na3BrO
C
C. CH3CH2OHNaBr
A. A
B. B
C. C
0%
0%
0%
D. D
B
B. CH3CH2OH + NaBr
What type of compound does this formula
represent?
CH3CH2CH2COOH
A. ester
A
0%
D
D. ketone
C
C. carboxylic acid
A. A
B. B
C. C
0%
0%
0%
D. D
B
B. ether
How many carbon atoms are present in
2-ethyl pentane?
A. 2
B. 5
D
A
0%
C
D. 8
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. 7
What are the oxidation numbers of the
elements in H2SO4?
A. H = +1, S = +6, O = –2
B. H = +2, S = +4, O = –4
D
A
0%
C
D. H = +1, S = –10, O = +2
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. H = +1, S = +4, O = –1
Which type of compound is formed when
accepts H+ ions?
A. Brønsted-Lowery base
B. Brønsted-Lowery acid
D
A
0%
C
D. conjugate acid
A. A
B. B
C. C
0%
0%
0%
D. D
B
C. conjugate base
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Table 22.1
Organic Compounds and
Their Functional Groups
Table 22.14
Common Polymers
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