Chapter 23 Functional Groups 23.2 Alcohols, Ethers, and Amines 23.1 Introduction to Functional Groups 23.2 Alcohols, Ethers, and Amines 23.3 Carbonyl Compounds 23.4 Polymers Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

How can organic chemistry cool you down? CHEMISTRY & YOU How can organic chemistry cool you down? Aftershave lotion contains a certain organic compound that imparts a cooling sensation on the skin. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the general formula of an alcohol? Alcohols Alcohols What is the general formula of an alcohol? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What do mouthwash, perfume, and hairspray have in common? Alcohols What do mouthwash, perfume, and hairspray have in common? They all contain an alcohol of some type. An alcohol is an organic compound with an —OH group. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The general formula of an alcohol is ROH. Alcohols The general formula of an alcohol is ROH. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols The —OH functional group in alcohols is called a hydroxy group, sometimes called a hydroxyl group. The oxygen atom in the —OH group has two pairs of electrons, which compress the R—O—H bond angle. As a result, an alcohol molecule has a bent shape. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Aliphatic alcohols can be classified into structural categories according to the number of carbons attached to the carbon with the hydroxy group. If only one carbon (or no carbon) is attached to C—OH, the latter carbon is considered a primary carbon, and the alcohol is a primary alcohol. Only one R group is attached to C—OH of a primary (abbreviated 1°) alcohol. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Aliphatic alcohols can be classified into structural categories according to the number of carbons attached to the carbon with the hydroxy group. If two carbons are attached, the carbon is a secondary carbon, which gives a secondary alcohol. Two R groups are attached to C—OH of a secondary (2°) alcohol. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Aliphatic alcohols can be classified into structural categories according to the number of carbons attached to the carbon with the hydroxy group. If three carbons are attached, the carbon is a tertiary carbon, and a tertiary alcohol. Three R groups are attached to C—OH of a tertiary (3°) alcohol. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Naming Alcohols Both IUPAC and common names are used for alcohols. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols To name aliphatic alcohols using the IUPAC system, drop the -e ending of the parent hydrocarbon name and add the ending -ol. The parent hydrocarbon is the longest continuous chain of carbons that includes the carbon attached to the hydroxy group. Ethanol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols To name aliphatic alcohols using the IUPAC system, drop the -e ending of the parent hydrocarbon name and add the ending -ol. The parent hydrocarbon is numbered so the position of the hydroxy group is given the lowest possible number. 2-propanol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Some alcohols have more than one hydroxy group. Naming Alcohols Some alcohols have more than one hydroxy group. To name these alcohols using the IUPAC system, simply add the ending -diol or -triol to the parent hydrocarbon name if the alcohol has two or three hydroxy groups, respectively. 1,2-ethanediol 1,2,3-propanetriol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols The common names of aliphatic alcohols are written in the same way as those of halocarbons. The alkyl group ethyl, for example, is named and followed by the word alcohol, as in ethyl alcohol. Ethyl alcohol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols The common names of aliphatic alcohols are written in the same way as those of halocarbons. The alkyl group ethyl, for example, is named and followed by the word alcohol, as in ethyl alcohol. The common name for an alcohol with two hydroxy groups is glycol. Ethyl alcohol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols When the hydroxy group is attached directly to an aromatic ring, the compound is called a phenol. To assign the IUPAC name, phenol is used as the parent hydrocarbon. 2-methylphenol Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Naming Alcohols When the hydroxy group is attached directly to an aromatic ring, the compound is called a phenol. To assign the IUPAC name, phenol is used as the parent hydrocarbon. Cresol is the common name for the o, m, and p constitutional isomers of methylphenol. 2-methylphenol (o-cresol) Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Interpret Data Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Properties of Alcohols Alcohols are capable of intermolecular hydrogen bonding, which is reflected in their physical properties. Alcohols boil at higher temperatures than alkanes and halocarbons containing a comparable number of atoms. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Properties of Alcohols Because alcohols are derivatives of water, they are somewhat soluble in water. Alcohols with up to four carbons are completely soluble in water. The solubility of alcohols with more than four carbons in the chain is usually much lower. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Properties of Alcohols Alcohols consist of two parts—the carbon chain and the hydroxy group. The carbon chain part is nonpolar and is not attracted to water. The hydroxy group is polar and strongly interacts with water through hydrogen bonding. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Properties of Alcohols Alcohols consist of two parts—the carbon chain and the hydroxy group. For alcohols of up to four carbons, the polarity of the hydroxy group overpowers the nonpolarity of the carbon chain. As a result, these alcohols are soluble in water. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Properties of Alcohols Alcohols consist of two parts—the carbon chain and the hydroxy group. For alcohols of up to four carbons, the polarity of the hydroxy group overpowers the nonpolarity of the carbon chain. As a result, these alcohols are soluble in water. As the number of carbon atoms increases, the nonpolarity of the carbon chain dominates, and the solubility of the alcohol decreases. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Uses of Alcohols 2-propanol, which is more familiarly known as rubbing alcohol, is often used as an antiseptic. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Alcohols Uses of Alcohols 1,2,3-propanetriol is highly soluble in water because it has three hydroxy groups. It has a tendency to absorb water from its surroundings. This quality makes it a valuable moistening agent in cosmetics, foods, and pharmaceuticals. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Some antifreezes use 1,2-ethanediol as the main ingredient. Alcohols Uses of Alcohols Some antifreezes use 1,2-ethanediol as the main ingredient. This alcohol has a high boiling point, 197°C, which helps prevent vehicle engines from overheating. Its advantages over liquids with high boiling points are its solubility in water and its low freezing point, –17.4°C. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Most ethanol is produced by yeast fermentation of sugar. Alcohols Uses of Alcohols Most ethanol is produced by yeast fermentation of sugar. Fermentation is the production of ethanol from sugars by the action of yeasts or bacteria. The enzymes of the yeasts or bacteria serve as catalysts for the transformation. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Bread rises because of fermentation. Alcohols Uses of Alcohols Bread rises because of fermentation. Glucose molecules in the dough are broken down by the following fermentation reaction. C6H12O6(aq) → 2CH3CH2OH(aq) + 2CO2(g) Glucose Ethanol Carbon dioxide Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What functional group do all alcohols contain? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What functional group do all alcohols contain? All alcohols contain an —OH functional group. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

How are addition reactions used in organic chemistry? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Addition Reactions The carbon-carbon single bonds in alkanes are not easy to break. In an alkene, however, one of the bonds in the double bond is somewhat weaker. This bond is easier to break than a carbon-carbon single bond. So, it is sometimes possible for a compound of general structure X—Y to add to a double bond. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Addition Reactions The carbon-carbon single bonds in alkanes are not easy to break. In an alkene, however, one of the bonds in the double bond is somewhat weaker. In an addition reaction, a substance is added at the double or triple bond of an alkene or alkyne. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Addition Reactions Addition reactions are an important method of introducing new functional groups to organic molecules. They are also used to convert alkenes to alkanes. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Addition Reactions In the general addition reaction shown below, X and Y represent the two parts of the compound that are added to the alkene. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The addition of water to an alkene is a hydration reaction. Addition Reactions Hydration Reactions The addition of water to an alkene is a hydration reaction. A hydration reaction results in the formation of an alcohol. The addition of water to ethane to form ethanol is a typical hydration reaction. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Halogenation Reactions Addition Reactions Halogenation Reactions When the reagent X—Y is a halogen molecule, the product of the reaction is a disubstituted halocarbon. The addition of bromine to ethene to form the disubstituted halocarbon 1,2-dibromoethane is an example. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Halogenation Reactions Addition Reactions Halogenation Reactions The addition of bromine to carbon-carbon multiple bonds is often used as a chemical test for unsaturation in an organic molecule. Bromine has an orange color, but most bromine-substituted organic compounds are colorless. After mixing, if the solution remains colorless, the compound is positive for unsaturation. If the solution remains orange, the compound is negative for unsaturation. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Halogenation Reactions Addition Reactions Halogenation Reactions Hydrogen halides, such as HBr or HCl, can also add to a double bond. Because the product contains only one substituent, it is called a monosubstituted halocarbon. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Hydrogenation Reactions Addition Reactions Hydrogenation Reactions The addition of hydrogen to a carbon-carbon double bond to produce an alkane is called a hydrogenation reaction. The manufacture of margarine or spreads from various oils is a common application of hydrogenation. Saturated fats have higher melting points than unsaturated fats. This is why margarine remains solid at room temperature. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Hydrogenation Reactions Addition Reactions Hydrogenation Reactions The hydrogenation of a double bond is a reduction reaction. Ethene is reduced to ethane. Cyclohexene is reduced to cyclohexane. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

How are hydration and hydrogenation reactions similar How are hydration and hydrogenation reactions similar? How are they different? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

How are hydration and hydrogenation reactions similar How are hydration and hydrogenation reactions similar? How are they different? Both hydration and hydrogenation reactions are addition reactions. Hydration is the addition of water to an alkene, and results in the formation of an alcohol. Hydrogenation is the addition of hydrogen, and results in the formation of an alkane. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the general formula of an ether? Ethers Ethers What is the general formula of an ether? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the general formula of an ether? Ethers Ethers What is the general formula of an ether? An ether is an organic compound in which oxygen is bonded to two carbon groups. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The general formula of an ether is ROR. Ethers The general formula of an ether is ROR. Like an alcohol, an ether molecule is bent because of the unshared pairs of electrons on the oxygen atom. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Ethers To name an ether using the IUPAC system, first you need to identify the two R groups. The smaller R group is treated as part of the substituent, and the -ane and -ene endings are replaced with -oxy. The larger R group is the parent hydrocarbon. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Ethers In the common names of ethers, both R groups are treated as substituents. The -ane or -ene endings are replaced with -yl for both R groups. List the names of the two R groups in alphabetical order and follow with the word ether. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

CHEMISTRY & YOU Menthol is the common name of the organic compound responsible for the cooling sensation in many consumer products. Menthol is a cyclohexanol with two alkyl substituents. Is menthol an alcohol or an ether? How can you tell? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

CHEMISTRY & YOU Menthol is the common name of the organic compound responsible for the cooling sensation in many consumer products. Menthol is a cyclohexanol with two alkyl substituents. Is menthol an alcohol or an ether? How can you tell? Menthol is an alcohol. The ending -ol always indicates an alcohol. An ether is indicated by the ending -oxy or by the word “ether.” Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

When both R groups are the same, the ether is symmetric. Ethers When both R groups are the same, the ether is symmetric. The common names of symmetric ethers use the prefix di-. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Diethyl ether was the first reliable general anesthetic. Ethers Diethyl ether was the first reliable general anesthetic. However, because diethyl ether is highly flammable and often causes nausea, it was eventually replaced by other anesthetics. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Ethers can form hydrogen bonds with water. Ethers usually have lower boiling points than alcohols of comparable molar mass, but higher boiling points than comparable hydrocarbons and halocarbons. Unlike alcohols, ethers are not capable of forming hydrogen bonds with other ether molecules. Ethers can form hydrogen bonds with water. Ethers are more soluble in water than hydrocarbons and halocarbons, but less soluble than alcohols because they form fewer hydrogen bonds. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the key difference between a symmetric ether and an asymmetric ether? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the key difference between a symmetric ether and an asymmetric ether? A symmetric ether has two of the same R groups attached to the oxygen atom; an asymmetric ether has two different R groups. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the general formula of an amine? Amines Amines What is the general formula of an amine? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What is the general formula of an amine? Amines Amines What is the general formula of an amine? An amine is an organic compound in which nitrogen is bonded to a carbon group. Amines are similar to ammonia (NH3). Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The general formula of an amine is RNH2, R2NH, or R3N. Amines The general formula of an amine is RNH2, R2NH, or R3N. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Amine Amines can be classified according to the number of R groups attached to the nitrogen atom. An amine with the general formula RNH2 is a primary amine because one R group is attached to the nitrogen atom. Amines with two or three R groups attached to the nitrogen atom are secondary or tertiary amines, respectively. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Amines The IUPAC system for naming primary amines is similar to that of alcohols. The -e ending of the parent hydrocarbon is changed to -amine. Ethanamine is used to make plastics, pharmaceuticals, and pesticides. Benzenamine is used to make furniture foam and some of the dyes that give clothes their colors. Benzenamine Ethanamine Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The common names of primary amines are similar to the IUPAC names. The alkyl or aryl group is named and followed by -amine. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Like alcohols, primary amines form intermolecular hydrogen bonds. Because nitrogen is less electronegative than oxygen, the hydrogen bonds in amines are not as strong as those in alcohols. As a result, primary amines have lower boiling points than alcohols with a comparable number of carbons. Amines can also hydrogen bond with water. Smaller amines are soluble in water, but as the number of carbons increase, the solubility in water decreases. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What functional group is characteristic of primary amines? Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

What functional group is characteristic of primary amines? Primary amines are characterized by having an —NH2 group. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

The general formula of an alcohol is ROH. Key Concepts The general formula of an alcohol is ROH. Addition reactions are an important method of introducing new functional groups to organic molecules. They are also used to convert alkenes to alkanes. The general formula of an ether is ROR. The general formula of an amine is RNH2, R2NH, or R3N. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

hydroxy group: the —OH functional group in alcohols Glossary Terms alcohol: an organic compound having an —OH (hydroxy) group; the general structure is R—OH hydroxy group: the —OH functional group in alcohols fermentation: the production of ethanol from sugars by the action of yeast or bacteria addition reaction: a reaction in which a substance is added at the double bond of an alkene or at the triple bond of an alkyne Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

hydration reaction: a reaction in which water is added to an alkene Glossary Terms hydration reaction: a reaction in which water is added to an alkene hydrogenation reaction: a reaction in which hydrogen is added to a carbon-carbon double bond to produce an alkane ether: an organic compound in which oxygen is bonded to two carbon groups; the general formula is R—O—R amine: an organic compound in which nitrogen is bonded to a carbon group Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

Carbon Chemistry and Reactions BIG IDEA Carbon Chemistry and Reactions Chemical reactions can be used to change the structure of organic molecules, often by introducing a new functional group. Addition reactions are commonly used in organic chemistry. Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.

END OF 23.2 Copyright © Pearson Education, Inc., or its affiliates. All Rights Reserved.