Lecture Presentation Chapter 12 Organic Compounds Karen C Timberlake General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter Introduction to Organic Chemistry: Hydrocarbons Firefighters/emergency medical technicians are first responders to fires, accidents, and other emergency situations They are required to have an emergency medical technician certification in order to be able to treat seriously injured people General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter 12 Readiness Core Chemistry Skills • • • Drawing Lewis Structures (6.6) Predicting Shape (6.8) Balancing a Chemical Equation (7.1) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc 12.1 Organic Compounds Organic chemistry is the study of carbon compounds Organic compounds such as vegetable oil contain carbon and hydrogen and are not soluble in water Learning Goal Identify properties characteristic of organic or inorganic compounds General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Organic Compounds An organic compound • • • Always contains carbon and hydrogen atoms May also contain other nonmetals such as oxygen, sulfur, nitrogen, phosphorus, or a halogen is often found in common products such as gasoline, medicines, shampoos, plastics, and perfumes We organize organic compounds by their functional groups, which are groups of atoms bonded in a specific way Compounds that contain the same functional group have similar physical and chemical properties General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Properties of Organic Compounds Organic compounds typically • • • Have covalent bonds have low melting and boiling points are flammable and undergo combustion • are not soluble in water Vegetable oil is a mixture of organic compounds and is not soluble in water General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Organic and Inorganic Compounds Many inorganic compounds have high melting and boiling points Inorganic compounds that are ionic are usually soluble in water, and most not burn in air Propane, C3H8, is an organic compound used as a fuel NaCl, + − salt, is an inorganic compound composed of Na and Cl ions General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Properties of Organic and Inorganic Compounds General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Identify each characteristic as most typical of compounds that are inorganic or organic A It has a high melting point B It is not soluble in water C It contains carbon and hydrogen atoms D It has the formula MgCl2 E It burns easily in air General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Solution Identify each characteristic as most typical of compounds that are inorganic or organic A It has a high melting point inorganic B It is not soluble in water organic C It contains carbon and hydrogen atoms D It has the formula MgCl2 E It burns easily in air General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake organic inorganic organic © 2016 Pearson Education, Inc Benzene, an Aromatic Compound Benzene is • • • • • an aromatic compound a ring of six C atoms, each bonded to one H atom a flat ring structure drawn with three alternating double bonds represented by two structures, because the electrons are shared equally among all the C atoms represented by a line-angle structural formula using a circle in the center instead of the alternating double bonds General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Aromatic Compounds Some common examples of aromatic compounds that we use for flavor are anisole from anise, estragole from tarragon, and thymol from thyme General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Benzene • Each carbon atom uses three valence electrons to bond to the hydrogen atom and two adjacent carbons The fourth valence electron was thought to be shared in a double bond with an adjacent carbon • In 1865, August Kekulé proposed that the carbon atoms in benzene were arranged in a flat ring with alternating single and double bonds between the adjacent carbon atoms General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Aromatic Compounds • • • Aromatic compounds containing a benzene ring and a single substituent are named as benzene derivatives Since the ring contains only one substituent, the ring is not numbered Some common names such as toluene, aniline, and phenol are allowed by IUPAC rules General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Aromatic Compounds • When a benzene ring is a substituent, — C6H5, it is named as a phenyl group General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Aromatic Compounds • When there are two or more substituents, the benzene ring is numbered to give the lowest numbers to the substituents General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Aromatic Compounds • When a common name such as toluene, phenol, or aniline can be used, • • the carbon atom attached to the methyl, hydroxyl, or amine group is numbered as carbon prefixes are used to show the position of the two substituents General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Aromatic Compounds • The common name xylene is used for the isomers of dimethylbenzene • If three or more substituents are attached to the benzene ring, they are numbered in the direction to give the lowest set of numbers and then named alphabetically General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Common Aromatic Compounds Toluene is used as a reactant to make drugs, dyes, and explosives such as TNT (trinitrotoluene) The benzene ring is also found in some amino acids (the building blocks of proteins) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Common Aromatic Compounds The benzene ring is found in pain relievers such as aspirin, acetaminophen, and ibuprofen; and in flavorings such as vanillin General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Properties of Aromatic Compounds The flat, symmetrical structure of benzene allows for interactions between the cyclic structures, which contributes to the higher melting points and boiling points of benzene and its derivatives General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Properties of Aromatic Compounds • Aromatic compounds are less dense than water, although they are usually more dense than other hydrocarbons • • • Halogenated benzene compounds are denser than water Aromatic hydrocarbons are insoluble in water and are used as solvents for other organic compounds Only aromatic compounds containing strongly polar functional groups such as — OH or — COOH will be somewhat soluble in water • Benzene and other aromatic compounds are resistant to reactions that break up the aromatic system, although they are flammable General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Select the correct name for each compound A chlorocyclohexane B chlorobenzene C 1-chlorobenzene A 1,2-dimethylbenzene B 1,4-dimethylbenzene C 1,3-dimethylbenzene General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Solution Select the correct name for each compound B chlorobenzene C 1,3-dimethylbenzene General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Concept Map General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc ... bonds and, therefore, a tetrahedral shape General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc General, Organic, and Biological Chemistry: ... H3C General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake CH3 H2C CH2 © 2016 Pearson Education, Inc Formulas of Cycloalkanes General, Organic, and Biological Chemistry: ... Goal Write the IUPAC names and draw the condensed structural formulas and skeletal formulas for alkanes and cycloalkanes General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen