Ch. 23—Functional Groups Vocabulary to know: functional group, halocarbon, substitution reaction, hydroxyl group, addition reaction, carboxyl group, polymer,

Ch. 23—Functional Groups• Vocabulary to know: functional

group, halocarbon, substitution reaction, hydroxyl group, addition reaction, carboxyl group, polymer, monomer, addition polymer, condensation polymer

• Know table 23.1• Know examples of polymers• Know Organic Molecules labs I

and II

What you need to know for ch. 7-9 and 22 Unit Exam: everything covered in first semester

What you need to know for ch. 22-23 quiz: ch. 22 (more extensive naming of hydrocarbons, drawing and recognizing isomers, combustion reactions), ch. 23 (functional groups with specific examples as in lab; polymers)

Functional Groups

•Organic compounds can be classified according to their functional groups.

–A functional group is a specific arrangement of atoms in an organic compound that is capable of characteristic chemical reactions.

23.1NEED TO KNOW

Functional Groups23.1

NEED TO KNOW THE COMPOUND TYPES

Functional Groups

• The hydrocarbon skeletons in the components of these products are chemically similar. Functional groups give each product unique properties and uses.

23.1

Halogen Substituents–A halocarbon is a carbon-containing compound with a halogen substituent. –Halocarbons are a class of organic compounds containing covalently bonded fluorine, chlorine, bromine, or iodine.

23.1

On the basis of their common names, halocarbons in which a halogen is attached to a carbon of an aliphatic chain are called alkyl halides. Halocarbons in which a halogen is attached to a carbon of an arene ring are called aryl halides.

NEED TO KNOW

Halogen Substituents

23.1

Learned phenyl in ch. 22—remember this

Halogen Substituents

• The figure below shows the IUPAC names, structural formulas, and space-filling models for three simple hydrocarbons.

23.1NEED TO KNOW

Halogen Substituents23.1

Substitution Reactions

• A common type of organic reaction is a substitution reaction, in which an atom, or a group of atoms, replaces another atom or group of atoms.

–A halogen can replace a hydrogen atom on an alkane to produce a halocarbon.

23.1NEED TO KNOW


• A Generalized Equation and a Specific One

23.1NEED TO KNOW


• Treating benzene with a halogen in the presence of a catalyst causes the substitution of a hydrogen atom in the ring.

23.1NEED TO KNOW


• Halogens on carbon chains are readily displaced by hydroxide ions to produce an alcohol and a salt. The general reaction is as follows.

23.1


• Halocarbons also undergo substitution reactions.

23.1

23.1 Section Quiz.1. Organic molecules are classified according to

theira. functional groups.b. longest chain.c. derivatives.d. number of rings.

23.1 Section Quiz

2. What is the correct IUPAC name for the compound CH2BrCH2CH2Br?

a. methylbromoethylbromideb. dibromopropanec. 1,3-dibromopropaned. propyl-1,3-dibromide

23.1 Section Quiz

3. Which reaction will produce a halocarbon?a. hydrogenation of an alkyl halideb.substitution reaction of a halogen with an alkanec.reaction of potassium hydroxide with an aryl halided. reaction of sodium hydroxide with an alkyl halide

23.1 Section Quiz

4. In a substitution reaction, one of the products formed when CH3CH2Br and OH- ions react is

a. CH3CHBrOH.

b. CH3CH2OH.

c. CH3CHBr.

d. CH3CHO.

Alcohols– An alcohol is an organic compound with an — OH group. – The —OH functional group in alcohols is called a hydroxyl group

or hydroxy function.

23.2NEED TO KNOW

Alcohols

– Aliphatic alcohols can be classified into structural categories according to the number of R groups attached to the carbon with the hydroxyl group.

– When using the IUPAC system to name continuous-chain and substituted alcohols, drop the -e ending of the parent alkane name and add the ending -ol.

23.2NEED TO KNOW

Alcohols23.2

Alcohols23.2

Alcohols23.2

Alcohols• Alcohols can have more than one hydroxyl

group.

23.2

Alcohols

• These alcohols contain one, two, or three hydroxyl groups.

23.2

Alcohols• Ethanol (ethyl alcohol) is a

common component of many household products.

23.2NEED TO KNOW

Alcohols

• Aliphatic alcohols are used in many household products, including antiseptics, antifreeze, and cosmetics.

23.2NEED TO KNOW

Properties of Alcohols

– Alcohols of up to four carbons are soluble in water in all proportions. The solubility of alcohols with four or more carbons in the chain is usually much lower.

23.2


• Fermentation is the production of ethanol from sugars by the action of yeast or bacteria. A second reaction product, carbon dioxide, causes bread to rise.

23.2NEED TO KNOW


• Ethanol is the intoxicating substance in alcoholic beverages. It is a depressant that can be fatal if taken in large doses at once.

– Denatured alcohol is ethanol with an added substance to make it toxic (poisonous).

– Denatured alcohol is used as a reactant or as a solvent in industrial processes.

23.2NEED TO KNOW

Addition Reactions

• Addition reactions of alkenes are an important method of introducing new functional groups into organic molecules.

» In an addition reaction, a substance is added at the double or triple bond of an alkene or alkyne.

» Double and triple bonds between carbon atoms are much more reactive than single bonds between carbon atoms.

23.2NEED TO KNOW

Addition Reactions

• Addition Across a Double Bond

23.2NEED TO KNOW

Addition Reactions23.2

Addition Reactions

• The addition of water to an alkene is a hydration reaction.

23.2


Addition Reactions

• The addition of hydrogen to a carbon–carbon double bond to produce an alkane is called a hydrogenation reaction.

23.2



Ethers

– The general structure of an ether is R—O—R. The alkyl groups attached to the ether linkage are named in alphabetical order and are followed by the word ether.

23.2

Ethers

• An ether is a compound in which oxygen is bonded to two carbon groups.

23.2

Ethers23.2

23.2 Section Quiz.1.Choose the correct words for the spaces. The

structure of a secondary alcohol has ___________ attached to the __________ group.

a. two R groups, OH b. two OH groups, R c. one R group, C—OH d. two R groups, C—OH

23.2 Section Quiz.

2.Choose the correct words for the space. Alcohols that are completely soluble in water have _________ carbons in the chain.

a. four or lessb. three or lessc. four or mored. more than four

23.2 Section Quiz.

3.What type of reaction would convert CH2=CH—CH3 into CHBr—CHBr—CH3?

a. substitutionb. hydrogenationc. additiond. hydration

23.2 Section Quiz.

4.Which structure is ethylmethyl ether?a. CH3—CH2—OH—CH2

b. CH3—CH2—CHO

c. CH3CH2—O— CH3

d. CH2CH—CH3—OH

Aldehydes and Ketones

• A carbonyl group is a functional group with the general structure C═O.

– The C═O functional group is present in aldehydes and ketones.

23.3


• An aldehyde is an organic compound in which the carbon of the carbonyl group is always joined to at least one hydrogen.

23.3


• A ketone is an organic compound in which the carbon of the carbonyl group is joined to two other carbons.

23.3

Aldehydes and Ketones23.3


– Properties of Aldehydes and Ketones

23.3

Aldehydes and Ketones– Uses of Aldehydes and Ketones

• Many aldehydes and ketones have distinctive odors.– Aromatic aldehydes are often used as flavoring agents. – Benzaldehyde is known as oil of bitter almond. – Cinnamaldehyde is the source of the odor of oil of cinnamon.

23.3


• Vanillin, an aldehyde, comes from vanilla beans.

23.3


• A solvent used to remove nail polish is acetone, a ketone.

23.3

Carboxylic Acids– A carboxyl group consists of a carbonyl group attached to a

hydroxyl group. – A carboxylic acid is a compound with a carboxyl group.

23.3NEED TO KNOW

Carboxylic Acids• The general formula for a carboxylic acid is RCOOH.

– Carboxylic acids are weak because they ionize slightly in solution to give a carboxylate ion and a hydrogen ion.

23.3NEED TO KNOW

Carboxylic Acids

• Carboxylic acids give a variety of foods—spoiled as well as fresh—a distinctive sour taste.

23.3NEED TO KNOW

Carboxylic Acids– Low-molar-mass carboxylic acids are volatile liquids with

sharp, unpleasant odors. – The higher-mass carboxylic acids are nonvolatile, waxy,

odorless solids with low melting points.– Many continuous-chain carboxylic acids were first isolated

from fats and are called fatty acids. – Stearic acid, an 18-carbon acid obtained from beef fat, is used

to make inexpensive wax candles.

23.3

Carboxylic Acids23.3NEED TO KNOW first four carboxylic acids…see the pattern

Esters

– Esters contain a carbonyl group and an ether link to the carbonyl carbon. The general formula for an ester is RCOOR.

23.3

Esters

• Esters are derivatives of carboxylic acids in which the —OH of the carboxyl group has been replaced by an —OR from an alcohol.

23.3

Esters

• Esters may be prepared from a carboxylic acid and an alcohol.

23.3

Esters23.3

Esters23.3

Esters

• Ethyl ethanoate is a low-molar-mass ester.

23.3

Esters

• Esters impart the characteristic aromas and flavors of many flowers and fruits. Marigolds, raspberries, and bananas all contain esters.

23.3

Oxidation-Reduction Reactions

• The loss of hydrogen is a dehydrogenation reaction. – Dehydrogenation is an oxidation reaction because the loss of

each molecule of hydrogen involves the loss of two electrons from the organic molecule.

23.3

Oxidation-Reduction Reactions23.3




• Energy produced by oxidation reactions is used in both living and nonliving systems.

23.3





• An aldehyde is mixed with Fehling’s reagent (left test tube) and heated. The blue copper(II) ions in Fehling’s reagent are reduced to form Cu2O, a red precipitate (right test tube).

23.3

23.3 Section Quiz

1.Which compound is a ketone?a. CH3COOH

b. CH3CH2OH

c. CH3CHO

d. CH3COCH3

23.3 Section Quiz.

2.The IUPAC name for the structure CH3CH2COOH isa. ethanoic acid.b. acetic acid.c. propanoic acid.d. propionic acid.

23.3 Section Quiz.3.The product of the reaction between an alcohol

and a carboxylic acid is called a. a ketone.b. an ether.c. an ester.d. an aldehyde.

23.3 Section Quiz.4.Choose the correct words for the spaces.

Dehydrogenation is __________ reaction because losing a molecule of hydrogen involves the _______________ electrons from the organic molecule.

a. an oxidation, loss of two b. an oxidation, loss of four c. a reduction, gain of two d. a reduction, gain of four

Addition Polymers– A polymer is a large molecule formed by the covalent bonding

of repeating smaller molecules. – The smaller molecules that combine to form a polymer are

called monomers.

23.4NEED TO KNOW

Addition Polymers

• An addition polymer forms when unsaturated monomers react to form a polymer.

23.4

Addition Polymers

• Polyethylene is used to make many household items, including plastic bottles, bags, and food containers.

23.4NEED TO KNOW

Addition Polymers

• Polypropylene, a stiffer polymer than polyethylene, is used to make plastic utensils and containers, and other items such as this whistle.

23.4NEED TO KNOW

Addition Polymers

• Polypropylene is prepared by the polymerization of propene.

23.4

Addition Polymers• Polystyrene foam is a poor heat conductor, useful for

insulating homes and for molded items such as coffee cups and picnic coolers.

23.4NEED TO KNOW

Addition Polymers

• Polyvinyl chloride (PVC) is used for pipes in plumbing. It is also produced in sheets, sometimes with a fabric backing, for use as a tough plastic upholstery covering.

23.4NEED TO KNOW

Addition Polymers

• Polyvinyl chloride (PVC) is a halocarbon polymer. Vinyl chloride is the monomer of polyvinyl chloride.

23.4

Addition Polymers

• Polytetrafluoroethene (Teflon™or PTFE) is the product of the polymerization of tetrafluoroethene monomers.

23.4

Addition Polymers

• PTFE is very resistant to heat and chemical corrosion. It is used to coat cookware and to insulate wires, cables, motors, and generators.

23.4

Addition Polymers

• Rubber is harvested from tropical plants and is used in a variety of products.

23.4NEED TO KNOW

Addition Polymers

• Polyisoprene, harvested from tropical plants such as a rubber tree, is the polymer that constitutes rubber.

23.4

Condensation Polymers

• Condensation polymers are formed by the head-to-tail joining of monomer units.

23.4NEED TO KNOW

Condensation Polymers• Polyesters are made by linking dicarboxylic acids and

dihydroxy alcohols. The polyester polyethylene terephthalate (PET) is formed from terephthalic acid and ethylene glycol.

23.4NEED TO KNOW


• Woven Dacron (PET fibers) tubing can be used to replace major blood vessels.

23.4


• Polyamides are polymers in which the carboxylic acid and amine monomer units are linked by amide bonds.

23.4


• The representative polymer unit of nylon is derived from 6-aminohexanoic acid, a compound that contains both carboxyl and amino functional groups.

23.4


• Nylon fibers are used for carpeting, tire cord, fishing lines, sheer hosiery, and textiles.

23.4NEED TO KNOW


• Kevlar™is a polyamide made from terephthalic acid and p-phenylenediamine.

23.4NEED TO KNOW


• Kevlar is used extensively where strength and flame resistance are needed. Bulletproof vests are made of Kevlar.

23.4NEED TO KNOW

23.4 Section Quiz.

1. A reactant used to form addition polymers must a. be saturated.b. be unsaturated.c. be an alkane.d. contain only single C-C bonds.

23.4 Section Quiz.2. The physical properties of addition polymers are

controlled by adjusting the a. length of the carbon chain.b. temperature of the reaction.c. catalyst used in the reaction.d. number of substituents.

23.4 Section Quiz.3. When water is produced as a polymer forms, the

polymer is most likely a. a condensation polymer.b. an addition polymer.c. polyethylene.d. a dicarboxylic acid.

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Ch. 23—Functional Groups Vocabulary to know: functional group, halocarbon, substitution reaction, hydroxyl group, addition reaction, carboxyl group, polymer,