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Chapter 22: Substituted Hydrocarbons and Their Reactions

CHEMISTRY Matter and Change. Chapter 22: Substituted Hydrocarbons and Their Reactions. Table Of Contents. CHAPTER 22. Section 22.1 Alkyl Halides and Aryl Halides Section 22.2 Alcohols, Ethers, and Amines Section 22.3 Carbonyl Compounds

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Chapter 22: Substituted Hydrocarbons and Their Reactions

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  1. CHEMISTRY Matter and Change Chapter 22: Substituted Hydrocarbons and Their Reactions

  2. Table Of Contents CHAPTER22 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 22.5Polymers Click a hyperlink to view the corresponding slides. Exit

  3. Alkyl Halides and Aryl Halides SECTION22.1 • 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.

  4. Alkyl Halides and Aryl Halides SECTION22.1 functional group halocarbon alkyl halide aryl halide plastic substitution reaction halogenation A halogen atom can replace a hydrogen atom in some hydrocarbons.

  5. Alkyl Halides and Aryl Halides SECTION22.1 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.

  6. Alkyl Halides and Aryl Halides SECTION22.1 Functional Groups (Cont.)

  7. Alkyl Halides and Aryl Halides SECTION22.1 Organic Compounds Containing Halogens • Any organic compound that contains a halogen substituent is called a halocarbon. • An alkyl halideis an organic compound containing a halogen atom covalently bonded to an aliphatic carbon atom. • An aryl halideis an organic compound containing a halogen bonded to an aromatic group.

  8. Alkyl Halides and Aryl Halides SECTION22.1 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.

  9. Alkyl Halides and Aryl Halides SECTION22.1 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 plasticis a polymer that can be heated and molded while relatively soft.

  10. Alkyl Halides and Aryl Halides SECTION22.1 Organic Compounds Containing Halogens(cont.)

  11. Alkyl Halides and Aryl Halides SECTION22.1 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.

  12. Alkyl Halides and Aryl Halides SECTION22.1 Substitution Reactions(cont.)

  13. Alkyl Halides and Aryl Halides SECTION22.1 Substitution Reactions(cont.) • 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.

  14. Section Check SECTION22.1 Which of the following is NOT an alkyl halide? A.2-fluorobutane B.1,3-dichlorobenzene C.sodium chloride D.bromoethane

  15. Section Check SECTION22.1 An alkane with one or more halogen substituents is called what? A.aryl halide B.metal halide C.chlorofluorocarbon D.alkyl halide

  16. Alcohols, Ethers, and Amines SECTION22.2 • 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.

  17. Alcohols, Ethers, and Amines SECTION22.2 hydroxyl group alcohol denatured alcohol ether amine Oxygen and nitrogen are two of the most-common atoms found in organic functional groups.

  18. Alcohols, Ethers, and Amines SECTION22.2 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.

  19. Alcohols, Ethers, and Amines SECTION22.2 Alcohols (Cont.)

  20. Alcohols, Ethers, and Amines SECTION22.2 Alcohols (Cont.) • Alcohol is polar and mixes completely with water. • Denatured alcoholis ethanol with small amounts of noxious materials added to it. • Alcohol names are based on the alkane names, with the ending –ol.

  21. Alcohols, Ethers, and Amines SECTION22.2 • An ether is an organic compound containing an oxygen bonded to two carbon atoms.

  22. Alcohols, Ethers, and Amines SECTION22.2 Ethers (Cont.) • 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.

  23. Alcohols, Ethers, and Amines SECTION22.2 Amines • Aminescontain nitrogen atoms bonded to carbon atoms in aliphatic chains or aromatic rings. • Amines are primary, secondary, or tertiary depending on if there are one, two, or three hydrogen atoms replaced by organic groups. • Amines have the suffix –amine. • If more than one amino group is present, the prefixes di, tri, tetra, etc. are used.

  24. Section Check SECTION22.2 Which of the following is an alcohol? A.cyclohexamine B.1-chlorobutanol C.bromobutene D.butylpropyl ether

  25. Section Check SECTION22.2 Which functional group is present in an alcohol? A.hydroxyl group B.halogen C.aromatic ring D.amino group

  26. Carbonyl Compounds SECTION22.3 • 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.

  27. Carbonyl Compounds SECTION22.3 carbonyl group aldehyde ketone carboxylic acid carboxyl group ester amide condensation reaction Carbonyl compounds contain a double-bonded oxygen in the functional group.

  28. Carbonyl Compounds SECTION22.3 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.

  29. Carbonyl Compounds SECTION22.3 Organic Compounds Containing the Carbonyl Group(cont.)

  30. Carbonyl Compounds SECTION22.3 Organic Compounds Containing the Carbonyl Group(cont.) • 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. • Ketones and aldehydes share many chemical and physical properties because their structures are similar.

  31. Carbonyl Compounds SECTION22.3 Organic Compounds Containing the Carbonyl Group(cont.) • Ketones are popular solvents for moderately polar substances. • Ketones are somewhat soluble in water.

  32. Carbonyl Compounds SECTION22.3 Organic Compounds Containing the Carbonyl Group(cont.)

  33. Carbonyl Compounds SECTION22.3 Carboxylic Acids • Carboxylic acidsare 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.

  34. Carbonyl Compounds SECTION22.3 Carboxylic Acids (cont.)

  35. Carbonyl Compounds SECTION22.3 Carboxylic Acids (cont.) • Carboxylic groups are represented by –COOH. • Carboxylic acids are polar and reactive, and ionize in water to form acids.

  36. Carbonyl Compounds SECTION22.3 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.

  37. Carbonyl Compounds SECTION22.3 Organic Compounds Derived from Carboxylic Acids (Cont.) • 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.

  38. Carbonyl Compounds SECTION22.3 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.

  39. Carbonyl Compounds SECTION22.3 Organic Compounds Derived from Carboxylic Acids (Cont.) • The amide functional group is found repeated many times in natural proteins and some synthetic materials.

  40. Carbonyl Compounds SECTION22.3 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.

  41. Section Check SECTION22.3 Which of the following is the carbonyl group? A.COOH B.C=O C.CONH2 D.R-O-R′

  42. Section Check SECTION22.3 Which of the following does NOT contain a carbonyl group? A.ketones B.esters C.amines D.aldehydes

  43. Other Reactions of Organic Compounds SECTION22.4 • Classify an organic reaction into one of five categories: substitution, addition, elimination, oxidation-reduction, or condensation. • Use structural formulas to write equations for reactions of organic compounds. • Predict the products of common types of organic reactions. catalyst: a substance that increases the rate of a chemical reaction by lowering activation energies but is not consumed in the reaction

  44. Other Reactions of Organic Compounds SECTION22.4 elimination reaction dehydrogenation reaction dehydration reaction addition reaction hydration reaction hydrogenation reaction Classifying the chemical reactions of organic compounds makes predicting products of reactions much easier.

  45. Other Reactions of Organic Compounds SECTION22.4 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.

  46. Other Reactions of Organic Compounds SECTION22.4 • 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.

  47. Other Reactions of Organic Compounds SECTION22.4 • A reaction that eliminates two hydrogen atoms is called a dehydrogenation reaction.

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