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)

23.1 NEED TO KNOW 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.

23.1 NEED TO KNOW THE COMPOUND TYPES Functional Groups

23.1 Functional Groups The hydrocarbon skeletons in the components of these products are chemically similar. Functional groups give each product unique properties and uses. Many consumer products contain hydrocarbon derivatives. The hydrocarbon skeletons in these products are chemically similar. Functional groups give each product unique properties and uses.

Halogen Substituents 23.1 NEED TO KNOW 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. 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.

23.1 Halogen Substituents Learned phenyl in ch. 22—remember this

23.1 NEED TO KNOW Halogen Substituents The figure below shows the IUPAC names, structural formulas, and space-filling models for three simple hydrocarbons. Structural formulas and space-filling models of halocarbons. a) The common name for chloromethane is methyl chloride. b) The common name for chloroethene is vinyl chloride. c) The common name for chlorobenzene is phenyl chloride.

23.1 Halogen Substituents

Substitution Reactions 23.1 NEED TO KNOW 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.

Substitution Reactions 23.1 NEED TO KNOW Substitution Reactions A Generalized Equation and a Specific One

Substitution Reactions 23.1 NEED TO KNOW Substitution Reactions Treating benzene with a halogen in the presence of a catalyst causes the substitution of a hydrogen atom in the ring.

Substitution Reactions 23.1 Substitution Reactions Halogens on carbon chains are readily displaced by hydroxide ions to produce an alcohol and a salt. The general reaction is as follows.

Substitution Reactions 23.1 Substitution Reactions Halocarbons also undergo substitution reactions.

23.1 Section Quiz. 1. Organic molecules are classified according to their a. 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. methylbromoethylbromide b. dibromopropane c. 1,3-dibromopropane d. propyl-1,3-dibromide

23.1 Section Quiz 3. Which reaction will produce a halocarbon? a. hydrogenation of an alkyl halide substitution reaction of a halogen with an alkane reaction of potassium hydroxide with an aryl halide d. 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. NEED TO KNOW 23.2 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.

23.2 NEED 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.

23.2 Alcohols

23.2 Alcohols

23.2 Alcohols

23.2 Alcohols Alcohols can have more than one hydroxyl group.

Alcohols These alcohols contain one, two, or three hydroxyl groups. 23.2 Alcohols These alcohols contain one, two, or three hydroxyl groups. These alcohols contain one, two, or three hydroxyl groups. Classifying Which space-filling model depicts a diol? A triol?

23.2 NEED TO KNOW Alcohols Ethanol (ethyl alcohol) is a common component of many household products. Ethanol (ethyl alcohol) is a common component of many household products.

23.2 NEED TO KNOW Alcohols Aliphatic alcohols are used in many household products, including antiseptics, antifreeze, and cosmetics. Aliphatic alcohols are used in many common household products. a) Isopropyl alcohol is an effective antiseptic. b) Ethylene glycol is the main ingredient in antifreeze. c) Many cosmetic products contain glycerol. Applying Concepts How does antifreeze prevent the water in a car’s radiator from freezing at 0°C and boiling at 100°C?

Properties of Alcohols 23.2 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.

Properties of Alcohols 23.2 NEED TO KNOW Properties of Alcohols 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. Cracker and bread dough are both made primarily of flour and water, but bread dough also contains yeast. Carbon dioxide, a product of sugar fermentation by yeast, causes bread to rise. Inferring What happens to the ethanol that is also produced?

Properties of Alcohols 23.2 NEED TO KNOW Properties of Alcohols 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.

23.2 NEED 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.

23.2 NEED TO KNOW Addition Reactions Addition Across a Double Bond

23.2 Addition Reactions

23.2 Addition Reactions The addition of water to an alkene is a hydration reaction.

23.2 Addition Reactions Bromine can be used to identify unsaturated compounds. a) Bromine has a brownish-orange color. b) A few drops of bromine solution are added to an unsaturated organic compound. c) The bromine reacts to form a colorless halocarbon.

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 Addition Reactions

23.2 Addition Reactions

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 Ethers Ethers are either nonsymmetric or symmetric. Ethylmethyl ether is an example of a nonsymmetric ether. Diphenyl ether is a symmetric ether. Both space-filling and ball-and-stick models of each ether are shown. Interpreting Visuals Describe the differences between a nonsymmetric ether and a symmetric ether.

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 less b. three or less c. four or more d. more than four

23.2 Section Quiz. 3. What type of reaction would convert CH2=CH—CH3 into CHBr—CHBr—CH3? a. substitution b. hydrogenation c. addition d. 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

23.3 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 Aldehydes and Ketones An aldehyde is an organic compound in which the carbon of the carbonyl group is always joined to at least one hydrogen. These low molar-mass carbonyl group compounds are completely soluble in water. a) Methanal is commonly known as formaldehyde. b) Ethanal is commonly known as acetaldehyde.. Interpreting Diagrams Use the structures to explain why these compounds are soluble in water.

23.3 Aldehydes and Ketones A ketone is an organic compound in which the carbon of the carbonyl group is joined to two other carbons. These low molar-mass carbonyl group compounds are completely soluble in water. c) Propanone is commonly known as acetone. Interpreting Diagrams Use the structures to explain why these compounds are soluble in water.

Aldehydes and Ketones 23.3

23.3 Aldehydes and Ketones Properties of Aldehydes and Ketones

Aldehydes and Ketones Uses 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.

Aldehydes and Ketones Vanillin, an aldehyde, comes from vanilla beans. 23.3 Aldehydes and Ketones Vanillin, an aldehyde, comes from vanilla beans. Vanilla beans, the seed pods of the vanilla orchid, are the natural source of this vanilla flavoring for ice cream and other foods.

23.3 Aldehydes and Ketones A solvent used to remove nail polish is acetone, a ketone. Many types of nail polish remover contain acetone, a common ketone.

23.3 NEED TO KNOW 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.

Carboxylic Acids The general formula for a carboxylic acid is RCOOH. 23.3 NEED 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. Carboxylic acids give a variety of foods—spoiled as well as fresh—a distinctive sour taste. Predicting What would you expect the pH range of aqueous solutions containing carboxylic acids to be?

23.3 NEED TO KNOW Carboxylic Acids Carboxylic acids give a variety of foods—spoiled as well as fresh—a distinctive sour taste. Carboxylic acids give a variety of foods—spoiled as well as fresh—a distinctive sour taste. Predicting What would you expect the pH range of aqueous solutions containing carboxylic acids to be?

23.3 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.

NEED TO KNOW first four carboxylic acids…see the pattern 23.3 Carboxylic Acids

23.3 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.

Esters Esters may be prepared from a carboxylic acid and an alcohol. 23.3 Esters Esters may be prepared from a carboxylic acid and an alcohol.

23.3 Esters

23.3 Esters

Esters Ethyl ethanoate is a low-molar-mass ester. 23.3 Ethyl ethanoate, shown with its structural formula and space-filling model, 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. Esters impart the characteristic aromas and flavors of many flowers and fruits. Marigolds, raspberries, and bananas all contain esters.

Oxidation-Reduction Reactions 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.

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions Energy produced by oxidation reactions is used in both living and nonliving systems. Oxidation reactions occur in many daily activities. a) These basketball players are energized by oxidation reactions taking place within the cells of their bodies. b) Much of the world relies on hydrocarbon combustion as a source of energy for vehicles.

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions

Oxidation-Reduction Reactions 23.3 Oxidation-Reduction Reactions 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). When 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). Inferring What is the oxidation state of copper in the product?

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 is a. 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

23.4 NEED TO KNOW 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.

23.4 Addition Polymers An addition polymer forms when unsaturated monomers react to form a polymer.

NEED TO KNOW 23.4 Addition Polymers Polyethylene is used to make many household items, including plastic bottles, bags, and food containers. Polyethylene is used for many familiar household items, including plastic bottles, bags, and food containers.

NEED TO KNOW 23.4 Addition Polymers Polypropylene, a stiffer polymer than polyethylene, is used to make plastic utensils and containers, and other items such as this whistle. Common polymers are used for various applications. Polypropylene is used in the manufacture of a variety of items, such as this whistle.

23.4 Addition Polymers Polypropylene is prepared by the polymerization of propene.

NEED TO KNOW 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.

23.4 NEED 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. Common polymers are used for various applications. Polyvinyl chloride is used for pipes in plumbing.

23.4 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. PTFE is used to coat cookware and to insulate wires, cables, motors, and generators. It also is suspended in motor oils as a friction-reducing agent.

23.4 NEED TO KNOW Addition Polymers Rubber is harvested from tropical plants and is used in a variety of products. Rubber is harvested from tropical plants and is used in a variety of products. Interpreting Photographs What is the source of natural polyisoprene?

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

Condensation Polymers NEED TO KNOW 23.4 Condensation Polymers Condensation polymers are formed by the head-to-tail joining of monomer units.

Condensation Polymers NEED TO KNOW 23.4 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.

Condensation Polymers 23.4 Condensation Polymers Woven Dacron (PET fibers) tubing can be used to replace major blood vessels. Woven Dacron (PET fibers) tubing can be used to replace major blood vessels. a) The blood vessel replacement before surgery. b) The blood vessel after surgery. Applying Concepts What properties of Dacron make it useful for this purpose?

Condensation Polymers 23.4 Condensation Polymers Polyamides are polymers in which the carboxylic acid and amine monomer units are linked by amide bonds.

Condensation Polymers 23.4 Condensation Polymers The representative polymer unit of nylon is derived from 6-aminohexanoic acid, a compound that contains both carboxyl and amino functional groups. Many types of nylon are polyamides. a) Flame-resistant clothing is made of Nomex™, a polyamide with aromatic rings. b) Nylon fishing lines are lightweight, yet very strong.

Condensation Polymers NEED TO KNOW 23.4 Condensation Polymers Nylon fibers are used for carpeting, tire cord, fishing lines, sheer hosiery, and textiles. Many types of nylon are polyamides. Nylon fishing lines are lightweight, yet very strong.

Condensation Polymers 23.4 NEED TO KNOW Condensation Polymers Kevlar™is a polyamide made from terephthalic acid and p-phenylenediamine. Bulletproof vests are made of Kevlar.

Condensation Polymers NEED TO KNOW 23.4 Condensation Polymers Kevlar is used extensively where strength and flame resistance are needed. Bulletproof vests are made of Kevlar. Bulletproof vests are made of Kevlar.

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.