Chapter 22: Substituted Hydrocarbons and Their Reactions

Chapter 22: Substituted Hydrocarbons and Their ReactionsChapter 22: Substituted Hydrocarbons and Their Reactions

CHEMISTRY Matter and Change

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 PolymersExit

CHAPTER

22 Table Of Contents

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• 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.

SECTION22.1

Alkyl Halides and Aryl Halides

functional group

halocarbon

alkyl halide

aryl halide

A halogen atom can replace a hydrogen atom in some hydrocarbons.

plastic

substitution reaction

halogenation

SECTION22.1

Alkyl Halides and Aryl Halides

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.

SECTION22.1

Alkyl Halides and Aryl Halides

SECTION22.1

Alkyl Halides and Aryl Halides

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.

SECTION22.1

Alkyl Halides and Aryl Halides

Organic Compounds Containing Halogens (cont.)• Organic molecules containing

functional groups are given IUPAC names based on their main chain alkane structures.

–For alkyl halides, a prefix indicating the halogen as follows: remove ine and add o. Ex. Fluoro, chloro, bromo, etc.

–If there is more than a single halogen, they are listed alphabetically.

SECTION22.1

Alkyl Halides and Aryl Halides

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.

SECTION22.1

Alkyl Halides and Aryl Halides

SECTION22.1

Alkyl Halides and Aryl Halides

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.

SECTION22.1

Alkyl Halides and Aryl Halides

Substitution Reactions (cont.)

SECTION22.1

Alkyl Halides and Aryl Halides

• 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.

SECTION22.1

Alkyl Halides and Aryl Halides

Substitution Reactions (cont.)

Which of the following is NOT an alkyl halide?

A. 2-fluorobutane

B. 1,3-dichlorobenzene

C. sodium chloride

D. bromoethane

SECTION22.1

Section Check

An alkane with one or more halogen substituents is called what?

A. aryl halide

B. metal halide

C. chlorofluorocarbon

D. alkyl halide

SECTION22.1

Section Check

• 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.

SECTION22.2

Alcohols, Ethers, and Amines

hydroxyl group

alcohol

denatured alcohol

ether

amine

Oxygen and nitrogen are two of the most-common atoms found in organic functional groups.

SECTION22.2

Alcohols, Ethers, and Amines

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.

SECTION22.2

Alcohols, Ethers, and Amines

Alcohols (Cont.)

SECTION22.2

Alcohols, Ethers, and Amines

• 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.

SECTION22.2

Alcohols, Ethers, and Amines

Alcohols (Cont.)

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

SECTION22.2

Alcohols, Ethers, and Amines

• 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.

SECTION22.2

Alcohols, Ethers, and Amines

Ethers (Cont.)

Amines• Amines contain nitrogen atoms

bonded to carbon atoms in aliphatic chains or aromatic rings.

SECTION22.2

Alcohols, Ethers, and Amines

• If more than one amino group is present, the prefixes di, tri, tetra, etc. are used.

• Amines have the suffix –amine.

• Amines are primary, secondary, or tertiary depending on if there are one, two, or three hydrogen atoms replaced by organic groups.

Which of the following is an alcohol?

A. cyclohexamine

B. 1-chlorobutanol

C. bromobutene

D. butylpropyl ether

SECTION22.2

Section Check

Which functional group is present in an alcohol?

A. hydroxyl group

B. halogen

C. aromatic ring

D. amino group

SECTION22.2

Section Check

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

electronegative: indicates the relative ability of an element’s atoms to attract electrons in a chemical bond

• Discuss the properties of compounds containing the carbonyl group.

SECTION22.3

Carbonyl Compounds

carbonyl group

aldehyde

ketone

carboxylic acid

Carbonyl compounds contain a double-bonded oxygen in the functional group.

carboxyl group

ester

amide

condensation reaction

SECTION22.3

Carbonyl Compounds

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.

SECTION22.3

Carbonyl Compounds

Organic Compounds Containing the Carbonyl Group (cont.)

SECTION22.3

Carbonyl Compounds

• 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.

SECTION22.3

Carbonyl Compounds

Organic Compounds Containing the Carbonyl Group (cont.)

• Ketones and aldehydes share many chemical and physical properties because their structures are similar.

• Ketones are popular solvents for moderately polar substances.

• Ketones are somewhat soluble in water.

SECTION22.3

Carbonyl Compounds

Organic Compounds Containing the Carbonyl Group (cont.)

SECTION22.3

Carbonyl Compounds

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.

SECTION22.3

Carbonyl Compounds

Carboxylic Acids (cont.)

SECTION22.3

Carbonyl Compounds

• Carboxylic groups are represented by –COOH.

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

SECTION22.3

Carbonyl Compounds

Carboxylic Acids (cont.)

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.

SECTION22.3

Carbonyl Compounds

• 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.

SECTION22.3

Carbonyl Compounds

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.

SECTION22.3

Carbonyl Compounds

Organic Compounds Derived from Carboxylic Acids (Cont.)

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

SECTION22.3

Carbonyl Compounds

Organic Compounds Derived from Carboxylic Acids (Cont.)

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.

SECTION22.3

Carbonyl Compounds

Which of the following is the carbonyl group?

A. COOH

B. C=O

C. CONH2

D. R-O-R′

SECTION22.3

Section Check

Which of the following does NOT contain a carbonyl group?

A. ketones

B. esters

C. amines

D. aldehydes

SECTION22.3

Section Check

• Classify an organic reaction into one of five categories: substitution, addition, elimination, oxidation-reduction, or condensation.

catalyst: a substance that increases the rate of a chemical reaction by lowering activation energies but is not consumed in the reaction

• Use structural formulas to write equations for reactions of organic compounds.

• Predict the products of common types of organic reactions.

SECTION22.4

Other Reactions of Organic Compounds

elimination reaction

dehydrogenation reaction

dehydration reaction

Classifying the chemical reactions of organic compounds makes predicting products of reactions much easier.

addition reaction

hydration reaction

hydrogenation reaction

SECTION22.4

Other Reactions of Organic Compounds

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.

SECTION22.4

Other Reactions of Organic Compounds

• The formation of alkenes from alkanes is an elimination reaction, where a combination of atoms is removed from two adjacent carbon atoms forming an additional bond between the two carbon atoms.

Other Reactions of Organic CompoundsSECTION22.4

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

Other Reactions of Organic CompoundsSECTION22.4

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

Other Reactions of Organic CompoundsSECTION22.4

• Addition reactions result when other atoms bond to two atoms bonded by 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.

Other Reactions of Organic CompoundsSECTION22.4

• 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.

Other Reactions of Organic CompoundsSECTION22.4

Other Reactions of Organic CompoundsSECTION22.4

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

Other Reactions of Organic CompoundsSECTION22.4

Classifying Reactions of Organic Substances (Cont.)

Other Reactions of Organic CompoundsSECTION22.4

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.

Other Reactions of Organic CompoundsSECTION22.4

Which type of reaction normally produces an alcohol from an alkene?

A. substitution

B. elimination

C. hydration

D. addition

SECTION22.4

Section Check

What type of reaction is the following?

alkyl halide → alkene

A. halogenation

B. elimination

C. addition

D. substitution

Section CheckSECTION22.4

• 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.

PolymersSECTION22.5

polymer

monomer

polymerization reaction

addition polymerization

Synthetic polymers are large organic molecules made up of repeating units that are linked together by addition or condensation reactions.

condensation polymerization

thermoplastic

thermosetting

PolymersSECTION22.5

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.

PolymersSECTION22.5

Reactions Used to Make Polymers

• 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.

PolymersSECTION22.5

PolymersSECTION22.5

Reactions Used to Make Polymers (cont.)

PolymersSECTION22.5

Reactions Used to Make Polymers (cont.)

PolymersSECTION22.5

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.

PolymersSECTION22.5

Reactions Used to Make Polymers (cont.)

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.

PolymersSECTION22.5

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

PolymersSECTION22.5

Properties and Recycling of Polymers (Cont.)

The smaller, repeating units that make up a polymer are called ____.

A. structural units

B. polyunits

C. monomers

D. building blocks

SECTION22.5

Section Check

One way polymers are synthesized is through ____ reactions.

A. condensation

B. elimination

C. substitution

D. dehydration

SECTION22.5

Section Check

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Study Guide

Chapter Assessment

Standardized Test Practice

Resources

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

• 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.

Alkyl Halides and Aryl HalidesSECTION22.1

Study Guide

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.

Key Concepts

Alcohols, Ethers, and AminesSECTION22.2

Study Guide

• 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.

Study Guide

Carbonyl CompoundsSECTION22.3

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.

Key Concepts

Study Guide

SECTION22.4

Other Reactions of Organic Compounds

• 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.

Study Guide

SECTION22.5

Polymers

Key Concepts

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

Chapter Assessment

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Amines contain which functional group?

A. –OH

B. –Br

C. R-O-R′

D. –NH2

Chapter Assessment

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Which of the following does NOT contain the carbonyl group?

A. ketones

B. ethers

C. aldehydes

D. amides

Chapter Assessment

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

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

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Chapter Assessment

A type of plastic that can be molded only when first produced is called a ____ .

A. thermoplastic

B. polythermal

C. setting plastic

D. thermosetting

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Chapter Assessment

What are the products of this reaction?

CH3CH2Br + NaOH → ____

A. CH3CH2Na + BrOH

B. CH3CH2OH + NaBr

C. CH3CH2OHNaBr

D. CH3CH3 + Na3BrO

Standardized Test Practice

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

What type of compound does this formula represent?

CH3CH2CH2COOH

A. ester

B. ether

C. carboxylic acid

D. ketone

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Standardized Test Practice

How many carbon atoms are present in 2-ethyl pentane?

A. 2

B. 5

C. 7

D. 8

Standardized Test Practice

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

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

Standardized Test Practice

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

Which type of compound is formed when a base accepts H+ ions?

A. Brønsted-Lowery base

B. Brønsted-Lowery acid

C. conjugate base

D. conjugate acid

Standardized Test Practice

Substituted Hydrocarbons and Their ReactionsCHAPTER

22

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