Chemistry: Matter and Change

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Chapter Menu
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
Section 22.1 Alkyl Halides and Aryl Halides

• Define functional group, and give examples.

aliphatic compound a nonaromatic hydrocarbon,
such as an alkane, an alkene, or an alkyne

• Compare and contrast alkyl and aryl halide
  structures.
• Evaluate the boiling points of organic halides.

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Section 22-1
Section 22.1 Alkyl Halides and Aryl Halides
(cont.)
functional group halocarbon alkyl halide aryl
halide
plastic substitution reaction halogenation
A halogen atom can replace a hydrogen atom in
some hydrocarbons.
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Section 22-1
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.

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Section 22-1
Functional Groups (cont.)
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• Functional groups

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Section 22-1
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.

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Section 22-1
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.

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• Do questions 1-3 page 740
• Check your answers on page 950

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Section 22-1
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.

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Section 22-1
Organic Compounds Containing Halogens (cont.)
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Section 22-1
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.

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Section 22-1
Substitution Reactions (cont.)
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Section 22-1
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.

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• Do questions 4-5 page 742

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Section 22-1
Section 22.1 Assessment
Which of the following is NOT an alkyl halide?
A. 2-fluorobutane B. 1,3-dichlorobenzene
C. sodium chloride D. bromoethane

• A
• B
• C
• D

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Section 22-1
Section 22.1 Assessment
An alkane with one or more halogen substituents
is called what? A. aryl halide B. metal halide
C. chlorofluorocarbon D. alkyl halide

• A
• B
• C
• D

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• quiz

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Study Guide 1
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.

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End of Section 22-1
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Section 22-2
Section 22.2 Alcohols, Ethers, and Amines

• Identify the functional groups that characterize
  alcohols, ethers, and amines.

miscible describes two liquids that are soluble
in each other

• Draw the structures of alcohols, ethers, and
  amines.
• Discuss the properties and uses of alcohols,
  ethers, and amines.

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Section 22-2
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.
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Section 22-2
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.

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Section 22-2
Alcohols (cont.)
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Section 22-2
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.

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Section 22-2
Ethers

• An ether is an organic compound containing an
  oxygen bonded to two carbon atoms.

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Section 22-2
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.

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Section 22-2
Amines

• Amines contain nitrogen atoms bonded to carbon
  atoms in aliphatic chains or aromatic rings.

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Section 22-2
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.

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• Do questions 9 and 11 page 746

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Section 22-2
Section 22.2 Assessment
Which of the following is an alcohol?
A. cyclohexamine B. 1-chlorobutanol
C. bromobutene D. butylpropyl ether

• A
• B
• C
• D

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Section 22-2
Section 22.2 Assessment
Which functional group is present in an alcohol?
A. hydroxyl group B. halogen C. aromatic ring
D. amino group

• A
• B
• C
• D

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• Alkyl Halides and Aryl Halides quiz

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Study Guide 2
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.

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End of Section 22-2
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Section 22-3
Section 22.3 Carbonyl Compounds

• Identify the structures of carbonyl compounds,
  including aldehydes, ketones, carboxylic acids,
  esters, and amides.

electronegative indicates the relative ability
of an elements atoms to attract electrons in a
chemical bond

• Discuss the properties of compounds containing
  the carbonyl group.

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Section 22-3
Section 22.3 Carbonyl Compounds (cont.)
carbonyl group aldehyde ketone carboxylic acid
carboxyl group ester amide condensation reaction
Carbonyl compounds contain a double-bonded oxygen
in the functional group.
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Section 22-3
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.

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Section 22-3
Organic Compounds Containing the Carbonyl Group
(cont.)
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Section 22-3
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.

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Section 22-3
Organic Compounds Containing the Carbonyl Group
(cont.)

• Ketones are popular solvents for moderately polar
  substances.

• Ketones are somewhat soluble in water.

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Section 22-3
Organic Compounds Containing the Carbonyl Group
(cont.)
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Section 22-3
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.

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Section 22-3
Carboxylic Acids (cont.)
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Section 22-3
Carboxylic Acids (cont.)

• Carboxylic groups are represented by COOH.

• Carboxylic acids are polar and reactive, and
  ionize in water to form acids.

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Section 22-3
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.

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Section 22-3
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.

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Section 22-3
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.

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Section 22-3
Organic Compounds Derived from Carboxylic Acids
(cont.)

• The amide functional group is found repeated many
  times in natural proteins and some synthetic
  materials.

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Section 22-3
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.

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• Do question 15 page 753

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Section 22-3
Section 22.3 Assessment
Which of the following is the carbonyl group?
A. COOH B. CO C. CONH2 D. R-O-R'

• A
• B
• C
• D

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Section 22-3
Section 22.3 Assessment
Which of the following does NOT contain a
carbonyl group? A. ketones B. esters
C. amines D. aldehydes

• A
• B
• C
• D

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• Self Check Quizzes section 3

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Study Guide 3
Section 22.3 Carbonyl Compounds
Key Concepts

• Carbonyl compounds are organic compounds that
  contain the CO group.

• Five important classes of organic compounds
  containing carbonyl compounds are aldehydes,
  ketones, carboxylic acids, esters, and amides.

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End of Section 22-3
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Section 22-4
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
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Section 22-4
Section 22.4 Other Reactions of Organic
Compounds (cont.)
elimination reaction dehydrogenation
reaction dehydration reaction
addition reaction hydration reaction hydrogenation
reaction
Classifying the chemical reactions of organic
compounds makes predicting products of reactions
much easier.
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Section 22-4
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.

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Section 22-4
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.

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Section 22-4
Classifying Reactions of Organic Substances
(cont.)

• A reaction that eliminates two hydrogen atoms is
  called a dehydrogenation reaction.

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Section 22-4
Classifying Reactions of Organic Substances
(cont.)

• An elimination reaction in which the atoms
  removed form water is called a dehydration
  reaction.

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Section 22-4
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.

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Section 22-4
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.

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Section 22-4
Classifying Reactions of Organic Substances
(cont.)
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Section 22-4
Classifying Reactions of Organic Substances
(cont.)

• Many organic compounds can be converted to other
  compounds by oxidation-reduction reactions.

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Section 22-4
Classifying Reactions of Organic Substances
(cont.)
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Section 22-4
Predicting Products of Organic Reactions

• Each type of reactionsubstitution, addition,
  elimination, oxidation-reduction, and
  condensationcan be used to predict the products
  of other organic reactions of the same types.

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Section 22-4
Section 22.4 Assessment
Which type of reaction normally produces an
alcohol from an alkene? A. substitution
B. elimination C. hydration D. addition

• A
• B
• C
• D

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Section 22-4
Section 22.4 Assessment
What type of reaction is the following? alkyl
halide ? alkene A. halogenation B. elimination
C. addition D. substitution

• A
• B
• C
• D

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Study Guide 4
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.

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End of Section 22-4
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Section 22-5
Section 22.5 Polymers

• Diagram the relationship between a polymer and
  the monomers from which it forms.

molecular mass the mass of one molecule of a
substance

• Classify polymerization reactions as addition or
  condensation.
• Predict polymer properties based on their
  molecular structures and the presence of
  functional groups.

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Section 22-5
Section 22.5 Polymers (cont.)
polymer monomer polymerization reaction addition
polymerization
condensation polymerization thermoplastic thermose
tting
Synthetic polymers are large organic molecules
made up of repeating units that are linked
together by addition or condensation reactions.
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Section 22-5
The Age of Polymers

• Polymers are large molecules consisting of many
  repeating structural units.
• Polyvinyl C2H4n

• Polyvinyl C2H4n
• The turn of the 20th century saw the advent of
  such polymers as rubber and celluloid.

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Section 22-5
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.

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Section 22-5
Reactions Used to Make Polymers (cont.)
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Section 22-5
Reactions Used to Make Polymers (cont.)
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Section 22-5
Reactions Used to Make Polymers (cont.)
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• Polymer animation

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Section 22-5
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.

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Section 22-5
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.

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Section 22-5
Properties and Recycling of Polymers (cont.)

• As fossil fuel supplies are depleted, recycling
  polymers becomes more important.

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Section 22-5
Section 22.5 Assessment
The smaller, repeating units that make up a
polymer are called ____. A. structural units
B. polyunits C. monomers D. building blocks

• A
• B
• C
• D

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Section 22-5
Section 22.5 Assessment
One way polymers are synthesized is through ____
reactions. A. condensation B. elimination
C. substitution D. dehydration

• A
• B
• C
• D

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• Section 5 quiz

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Study Guide 5
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.

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End of Section 22-5
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91
Study Guide 1
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.

92
Study Guide 2
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.

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Study Guide 3
Section 22.3 Carbonyl Compounds
Key Concepts

• Carbonyl compounds are organic compounds that
  contain the CO group.

• Five important classes of organic compounds
  containing carbonyl compounds are aldehydes,
  ketones, carboxylic acids, esters, and amides.

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Study Guide 4
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.

95
Study Guide 5
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.

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Chapter Assessment 1
Aryl halides contain what two groups?
A. nitrogen and aliphatic hydrocarbon chain
B. nitrogen and aromatic hydrocarbon ring
C. halogen and aromatic hydrocarbon ring
D. halogen and aliphatic hydrocarbon chain

• A
• B
• C
• D

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Chapter Assessment 2
Amines contain which function group? A. OH
B. Br C. R-O-R' D. NH2

• A
• B
• C
• D

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Chapter Assessment 3
Which of the following does NOT contain the
carbonyl group? A. ketones B. ethers
C. aldehydes D. amides

• A
• B
• C
• D

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Chapter Assessment 4
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 B. hydration reaction
C. dehydration reaction D. hydrogenation
reaction

• A
• B
• C
• D

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Chapter Assessment 5
A type of plastic that can be molded only when
first produced is called a ____.
A. thermoplastic B. polythermal C. setting
plastic D. thermosetting

• A
• B
• C
• D

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STP 1
What are the products of this reaction? CH3CH2Br
NaOH ? ____ A. CH3CH2Na BrOH B. CH3CH2OH
NaBr C. CH3CH2OHNaBr D. CH3CH3 Na3BrO

• A
• B
• C
• D

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STP 2
What type of compound does this formula
represent? CH3CH2CH2COOH A. ester B. ether
C. carboxylic acid D. ketone

• A
• B
• C
• D

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STP 3
How many carbon atoms are present in 2-ethyl
pentane? A. 2 B. 5 C. 7 D. 8

• A
• B
• C
• D

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STP 4
What are the oxidation numbers of the elements in
H2SO4? A. H 1, S 6, O 2 B. H 2, S
4, O 4 C. H 1, S 4, O 1 D. H 1,
S 10, O 2

• A
• B
• C
• D

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STP 5
Which type of compound is formed when accepts H
ions? A. Brønsted-Lowery base
B. Brønsted-Lowery acid C. conjugate base
D. conjugate acid

• A
• B
• C
• D

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CIM
Table 22.1 Organic Compounds and Their
Functional Groups Table 22.14 Common Polymers
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