Unit 12: Organic Chemistry

1. Unit 12: Organic Chemistry Chapter 22-24 Pre-AP Chemistry 1 Edmond North High School

2. Organic Chemistry • Organic chemistry is the chemistry of compounds containing carbon. • Carbon has the ability to form long chains. • Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form.

3. The Bonding of Carbon • Because carbon has four valence electrons, it can form four covalent bonds. • Carbon forms single, double, and triple bonds to achieve a filled octet. • A unique feature of carbon is its ability to bond with other carbons to form long chains or rings of various length.

4. Structure of Carbon Compounds • There are three hybridization states and geometries found in organic compounds: • sp3 Tetrahedral • sp2 Trigonal planar • sp Linear

5. Hydrocarbons • The 3 hybridization states of carbon give rise to four basic types: • Alkanes • Alkenes • Alkynes • Aromatic hydrocarbons

6. A hydrocarbon in which all the carbon atoms are connected to each other by single bonds is called a saturated hydrocarbon. Another name for a saturated hydrocarbon is an alkane. Although burning alkanes for fuel is their most common use, they are also used as solvents in paint removers, glues, and other products. Alkanes are the simplest hydrocarbons. Saturated Hydrocarbons

7. The carbons in an alkane can be arranged in a chain or a ring, and both chains and rings can have branches of other carbon chains attached to them. This means they are hydrocarbon chains where all the bonds between carbons are single bonds. Alkanes that have no branches are called straight-chain alkanes. Alkanes

8. Alkanes • The structural formulas for the first four straight-chain (or normal) alkanes are shown below. methane ethane propane butane

9. Some alkanes have a branched structure. In these compounds, a chain of one or more carbons is attached to a carbon in the longest continuous chain, which is called the parent chain. Alkanes

10. The carbon atoms in alkanes can also link up to form closed rings. The most common rings contain five or six carbons. The structures of these compounds can be drawn showing all carbon and hydrogen atoms. Alkanes

11. Structural diagrams can be simplified by using straight lines to represent the bonds between atoms in the rings. In these ring diagrams, each corner represents a carbon atom. Alkanes

12. Structural diagrams of straight- and branched-chain hydrocarbons also can be written in a simplified way by leaving out some of the bonds. For example, the formula for propane can be written as CH3—CH2—CH3. In this type of shorthand structure, the bonds between C and H are understood. In an even more simplified type of shorthand, the condensed structural formula for propane can be written as CH3CH2CH3. Here, the bonds both between C and C and between C and H are understood. Alkanes

13. To name a branched alkane, you must be able to answer three questions about its structure. How many carbons are in the longest continuous chain of the molecule? How many branches are on the longest chain and what is their size? To which carbons in the longest chain are the branches attached? For convenience, the carbon atoms in organic compounds are given position numbers. In straight-chain hydrocarbons, the numbering can begin at either end. It makes no difference. In branched hydrocarbons, the numbering begins at the end closest to the branch. Naming Alkanes

14. Name the compound pictured. Four carbons are in the longest continuous chain, so butane is the parent chain and will be part of the compound’s name. There is only one branch, and it contains one carbon. Instead of calling this a methane branch, change the -ane in methane to -yl. Thus, this is a methyl branch. Because the methyl branch is attached to the second carbon of the butane chain, this compound has the name 2-methylbutane. Naming Alkanes

15. Compounds that have the same formula but different structures are called isomers. Butane and 2-methylpropane are known as structural isomers. Each has the molecular formula C4H10, but they have different structural formulas because the carbon chains have different shapes. Isomers

16. Properties are affected by the structure or arrangement of atoms present in a molecule. Another factor that affects properties of alkanes is chain length. In general, the more carbons present in a straight-chain alkane, the higher its melting and boiling points. A property shared by all alkanes is their relative unreactivity. Because alkanes don’t have any polar bonds, they undergo only a small number of reactions and will dissolve only those organic compounds that are nonpolar or that have low polarity, such as oils and waxes. Properties of Alkanes

17. Cycloalkanes • The cycloalkanes are ringed, saturated hydrocarbons. • Five- and six-membered rings are most stable.

18. Unsaturated Hydrocarbons • A hydrocarbon that has one or more double or triple bonds between carbons is called an unsaturated hydrocarbon. • In saturated hydrocarbons, carbon atoms share only one pair, whereas in unsaturated hydrocarbons, the carbon atoms participating in double or triple bonds share two or three pairs.

19. A hydrocarbon in which one or more double bonds link carbon atoms together is called an alkene. Alkenes are named using the root names of the alkanes, with the -ane ending changed to -ene. Alkenes

20. Naming Alkenes • Use the following steps in naming alkenes. • Count the number of carbons in the longest continuous chain that contains the double bond, and assign the appropriate alkene name. • Number the carbons consecutively in the longest chain, starting at the end of the chain that will result in the lowest possible number for the first carbon to which the double bond is attached. • Write the number corresponding to the first carbon in the double bond, followed by a hyphen and then the alkene name. • Name: CH2 = CHCH2CH3

21. Double bonds prevent the carbons from rotating. If two different groups are attached to the carbons, the alkene can have two different structures called geometric isomers. In a cis- isomer, the similar groups are on the same side of the double bond. In a trans- isomer, the similar groups are on opposite sides of the double bond. Alkenes

22. Alkenes are more reactive than alkanes because the two extra electrons in the double bond are not held as tightly to the carbons as are the electrons in a single bond. Alkenes readily undergo synthesis reactions in which smaller molecules or ions bond to the atoms on either side of the double bond. An unsaturated alkene can be converted into a saturated alkane by adding hydrogen to the double bond. This reaction is called hydrogenation. Alkenes

23. Another type of unsaturated hydrocarbon, called an alkyne, contains a triple bond between two carbon atoms. Alkynes

24. Nomenclature of Alkynes 4-methyl-2-pentyne • Analogous to naming of alkenes. • Suffix is -yne rather than –ene.

25. Another group of unsaturated hydrocarbons has distinctive, six-carbon ring structures and are called aromatic hydrocarbons. The simplest compound in this group is benzene, with the molecular formula C6H6. Benzene contains six carbons joined together in a flat ring. Aromatic hydrocarbons were originally named because most of them have distinctive aromas. Aromatic Hydrocarbons

26. Aromatic hydrocarbons usually contain benzene rings-six membered rings of carbon atoms with alternating C-C single and C=C double bonds. In this hexagon, each corner represents a carbon atom. The circle in the middle of the structure represents the cloud of six electrons that are shared equally by the six carbon atoms in the molecule. Benzene

27. Aromatic Nomenclature • Many aromatic hydrocarbons are known by their common names.

28. Substituted hydrocarbons have a structure the same as hydrocarbons except for the substitution of atoms of another element for part of the hydrocarbons. The part of a molecule having a specific arrangement of atoms that is largely responsible for the chemical behavior of the parent molecule is called a functional group. Functional groups can be atoms, groups of atoms, or bond arrangements. Substituted Hydrocarbons

29. Carbon atoms can also form strong covalent bonds with other elements, the most common of which are oxygen, nitrogen, fluorine, chlorine, bromine, iodine, sulfur, and phosphorus. Atoms of these elements occur in organic substances as parts of functional groups. A functional group in an organic molecule is an atom or group of atoms that always reacts in a certain way. The addition of a functional group to a hydrocarbon structure always produces a substance with physical and chemical properties that differ from those of the parent hydrocarbon. Functional Groups

30. The symbols R and R′ represent any carbon chains or rings bonded to the functional group. And * represents a hydrogen atom, carbon chain, or carbon ring. Functional Groups

31. Organic Compounds and Their Functional Groups • The simplest functional groups can be thought of as substituent groups attached to a hydrocarbon. • The elements in group 7A of the periodic table—fluorine, chlorine, bromine, and iodine—are the halogens. • Any organic compound that contains a halogen substituent is called a halocarbon. • If you replace any of the hydrogen atoms in an alkane with a halogen atom, you form an alkyl halide.

32. An aryl halide is an organic compound containing a halogen atom bonded to a benzene ring or other aromatic group. The structural formula for an aryl halide is created by first drawing the aromatic structure and then replacing its hydrogen atoms with the halogen atoms specified. Organic Compounds Containing Halogens

33. An oxygen-hydrogen group covalently bonded to a carbon atom is called a hydroxyl group (—OH). An organic compound in which a hydroxyl group replaces a hydrogen atom of a hydrocarbon is called an alcohol. The general formula for an alcohol is ROH. Alcohols are named from parent hydrocarbon; suffix changed to -oland number designates carbon to which hydroxyl is attached. Alcohols are more acidic than other hydrocarbons. Alcohols

34. An ether is an organic compound containing an oxygen atom bonded to two carbon atoms. Ethers have the general formula ROR′. The simplest ether is one in which oxygen is bonded to two methyl groups. Note the relationship between methanol and methyl ether in the following diagram. Tend to be quite unreactive. Therefore, they are good polar solvents. Found in many fruits and perfumes Ethers

35. Another class of organic compounds contains nitrogen. Amines contain nitrogen atoms bonded to carbon atoms in aliphatic chains or aromatic rings and have the general formula RNH2. Generally have strong, unpleasant odors. Amines

36. The arrangement in which an oxygen atom is double-bonded to a carbon atom is called a carbonyl group. This group, which can be represented as shown below, is the functional group in organic compounds known as aldehydes and ketones. The Carbonyl Group

37. An aldehyde is an organic compound in which a carbonyl group located at the end of a carbon chain is bonded to a carbon atom on one side and a hydrogen atom on the other. Aldehydes have the general formula *CHO, where * represents an alkyl group or a hydrogen atom. Aldehydes

38. A carbonyl group also can be located within a carbon chain rather than at the end. A ketone is an organic compound in which the carbon of the carbonyl group is bonded to two other carbon atoms. Ketones have the general formula shown to the right. Ketones

39. A carboxylic acid is an organic compound that has a carboxyl group. A carboxyl group consists of a carbonyl group bonded to a hydroxyl group. Thus, carboxylic acids have the general formula shown to the right. Tart tasting. Carboxylic acids are weak acids. Carboxylic Acids

40. Several classes of organic compounds have structures in which the hydrogen or the hydroxyl group of a carboxylic acid is replaced by a different atom or group of atoms. The two most common classes are esters and amides. Organic Compounds Derived From Carboxylic Acids

41. An ester is any organic compound with a carboxyl group in which the hydrogen of the hydroxyl group has been replaced by an alkyl group, producing the following arrangement. Ester

42. An amide is an organic compound in which the —OH group of a carboxylic acid is replaced by a nitrogen atom bonded to other atoms. The general structure of an amide is shown to the right. Amides

43. A large molecule that is made up of many smaller, repeating units is called a polymer. A polymer forms when hundreds or thousands of these small individual units, which are called monomers, bond together in chains. The monomers that bond together to form a polymer may all be alike, or they may be different. Monomers and Polymers

44. A reaction in which the monomer units are bonded together to from a polymer is called a polymerization reaction. The repeating group of atoms in the monomer is called the structural unit of the polymer. The letter n is used to represent the number of structural units. The properties of a polymer are different from those of the monomers that formed it. Polymers

45. Polymers can have a wide variety of properties. Some, called plastics, can be heated and molded while relatively soft. A thermoplastic polymer is one that can be melted and molded repeatedly into shapes that are retained on cooling. A thermosetting polymer is one that can be molded when first prepared but when cool cannot be remelted. Polymers

46. Polymerization is a type of chemical reaction in which monomers are linked together one after another to make large chains. The two main types of polymerization reactions are addition polymerization and condensation polymerization. Polymerization Reactions

47. Another process that often occurs in combination with addition or condensation reactions is the linking together of many polymer chains. This is called cross-linking, and it gives additional strength to a polymer. In 1844, Charles Goodyear discovered that heating the latex from rubber trees with sulfur can cross-link the hydrocarbon chains in the liquid latex. The solid rubber that is formed can be used in tires and rubber balls. Rubber

48. In an addition reaction, monomers that contain double bonds add onto each other, one after another, to form long chains. The product of an addition polymerization reaction contains all of the atoms of the starting monomers. Addition Reactions

49. When monomers are added onto each other in addition polymerization, the double bonds are broken. Thus, all of the carbons in the main chain of an addition polymer are connected by single bonds. Addition Reactions

50. A hydration reaction is an addition reaction in which a hydrogen atom and a hydroxyl group from a water molecule add to a double or triple bond. A reaction that involves the addition of hydrogen to atoms in a double or triple bond is called a hydrogenation reaction. When H2 adds to the double bond of an alkene, the alkene is converted to an alkane. Addition Reactions