Chapter 11. Introduction to Organic Chemistry

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1 hapter 11 Introduction to rganic hemistry

2 Properties of arbon and its compounds 2

3 Properties of arbon and its compounds 3

4 Properties of arbon and its compounds 4

5 Properties of arbon and its compounds 5

6 Saturated ydrocarbons ydrocarbons are chemical compounds that contain only and atoms. Saturated hydrocarbons contain only single bonds. There are no double or triple bonds in these compounds. The primary source of hydrocarbons is petroleum and natural gas. 6

7 Alkanes The simplest saturated hydrocarbons are called alkanes. Methane, 4, is the simplest alkane. The alkanes form a series. Each member of the series differs by a specific number and kind of atoms. or 4 7

8 Naming Saturated ydrocarbons The International Union of Pure and Applied hemistry (IUPA) names for the first 12 "straight-chain" or "normal" alkanes are given in this table. Number of carbon atoms in chain Name Methane Ethane Propane Butane 5 6 Pentane exane 8

9 Naming Saturated ydrocarbons Number of carbon atoms in chain Name eptane ctane Nonane Decane Unidecane Dodecane 9

10 Alkanes The alkanes differ from each other by a 2 or methylene group. The boiling points of the alkanes increase with molecular weight. All alkanes have this general formula. n 2n+2 For example ethane, 2 6, and propane, 3 8, are the next two family members

11 Alkanes Isomers are chemical compounds that have the same molecular formulas but different structures. Two alkanes have the molecular formula They are a specific type of isomer called structural (constitutional) isomers. n-butane 2-methylpropane 11

12 Alkanes Three alkanes have the formula There are three structural isomers of pentane n-pentane 2-methylbutane 2,2-dimethylpropane The number of structural isomers increases rapidly with increasing numbers of carbon atoms. 12

13 Alkanes There are five isomeric hexanes, You draw them! n-hexane 13

14 onstitutional Isomers There are five isomeric hexanes, n-hexane 2-methylpentane 3-methylpentane ,2-dimethylbutane 2,3-dimethylbutane 14

15 Naming Saturated ydrocarbons ther organic compounds are named as derivatives of the alkanes. Branched-chain alkanes are named by the following rules. 1. hoose the longest continuous chain of carbon atoms which gives the basic name or stem. 15

16 Naming Saturated ydrocarbons 2 Number each carbon atom in the basic chain, starting at the end that gives the lowest number to the first group attached to the main chain (substituent). 3 For each substituent on the chain, we indicate the position in the chain (by an Arabic numeric prefix) and the kind of substituent (by its name). The position of a substituent on the chain is indicated by the lowest number possible. The number precedes the name of the substituent. 16

17 Naming Saturated ydrocarbons 4 When there are two or more substituents of a given kind, use prefixes to indicate the number of substituents. di = 2, tri = 3, tetra = 4, penta = 5, hexa = 6, hepta = 7, octa = 8, and so on. 5 The combined substituent numbers and names serve as a prefix for the basic hydrocarbon name. 6 Separate numbers from numbers by commas and numbers from words by hyphens. Words are "run together". 17

18 Naming Saturated ydrocarbons Alkyl groups (represented by the symbol R) are common substituents. Alkyl groups are fragments of alkanes in which one atom has been removed for the connection to the main chain. Alkyl groups have the general formula n 2n+1. In alkyl groups the -ane suffix in the name of the parent alkane is replaced by -yl. A one carbon group is named methyl. A two carbon group is named ethyl. A three carbon group is named propyl. 18

19 Unsaturated ydrocarbons The three classes of unsaturated hydrocarbons are: 1. alkenes, n 2n 2. alkynes, n 2n-2 3. aromatic hydrocarbons 19

20 Alkenes The simplest alkenes contain one = bond per molecule. The general formula for simple alkenes is n 2n. The first two alkenes are: ethene,

21 Alkenes The simplest alkenes contain one = bond per molecule. The general formula for simple alkenes is n 2n. The first two alkenes are: and propene,

22 Alkenes The systematic naming system for alkenes uses the same stems as alkanes. In the IUPA system, the -ane suffix for alkanes is changed to -ene. ommon names for the alkenes have the same stem but use the suffix -ylene is used. In chains of four or more atoms, a numerical prefix shows the position of the lowest-numbered doubly bonded atom. Always choose the longest chain that contains the = bond. 22

23 Alkynes Alkynes contain bonds. The simplest alkyne is 2 2, ethyne, or acetylene. Alkynes with only one bond have the formula n 2n-2. 23

24 Alkynes Alkynes are named like the alkenes except that the suffix -yne is used with the characteristic stem The alkyne stem is derived from the name of the alkane with the same number of carbon atoms. 3-heptyne 2-octyne 24

25 Aromatic ydrocarbons istorically, aromatic was used to describe pleasant smelling substances. Now it refers to benzene, 6 6, and derivatives of benzene. ther compounds that have similar chemical properties to benzene are also called aromatic. 25

26 Benzene The structure of benzene, 6 6, is: 26

27 Functional Groups Functional groups are groups of atoms that represent potential reaction sites. ompounds that contain a given functional group usually undergo similar reactions. Functional groups influence physical properties as well. 27

28 rganic alides A halogen atom may replace almost any hydrogen atom in a hydrocarbon. The functional group is the halide (-X) group. Examples include: chloroform, l 3 l l l 28

29 rganic alides 1,2-dichloroethane, l 2 2 l l l 29

30 Alcohols and Phenols The functional group in alcohols and phenols is the hydroxyl (-) group. Alcohols can be considered derivatives of hydrocarbons in which one or more atoms have been replaced by - groups. Alcohols are considered neutral compounds because they are only very slightly acidic. Alcohols can behave as acids but only in the presence of very strong bases. 30

31 Alcohols and Phenols Ethyl alcohol (ethanol), 2 5, is the most familiar alcohol. 31

32 Alcohols Alcohols can be classified into three classes: 1. Primary (1 ) alcohols like ethanol have the - group attached to a atom that has one bond to another atom

33 Alcohols and Phenols 2. Secondary(2 ) alcohols have the group attached to a atom that has bonds to 2 other atoms. For example,2-propanol:

34 Alcohols and Phenols 3. Tertiary (3 ) alcohols have the group attached to a atom that is bonded to 3 other atoms. For example, 2-methyl-2-propanol

35 Alcohols and Phenols The stem for the parent hydrocarbon plus an -ol suffix is the systematic name for an alcohol. A numeric prefix indicates the position of the - group in alcohols with three or more atoms. ommon names are the name of the appropriate alkyl group plus alcohol. 35

36 Alcohols pentanol 1-pentyl alcohol 2-pentanol 2-pentyl alcohol 3-pentanol 3-pentyl alcohol 36

37 Alcohols butanol 2-butanol methyl-1-propanol 2-methyl-2-propanol 37

38 Alcohols Because the - group is quite polar, the properties of alcohols depend upon the number of - groups per molecule and the size of the organic group. The boiling points of alcohols increase with increasing molecular weight. The solubility of alcohols in water decrease with increasing molecular weight 38

39 Ethers Ethers may be thought of as derivatives of water in which both atoms have been replaced by alkyl or aryl groups water an alcohol an ether 39

40 Ethers Ethers are not very polar and not very reactive. They are excellent solvents. ommon names are used for most ethers ethylmethyl ether dimethyl ether diethyl ether 40

41 Aldehydes and Ketones The functional group in aldehydes and ketones is the carbonyl group. R1 R2 or carbonyl group 41

42 Aldehydes and Ketones Except for formaldehyde, aldehydes have one atom and one organic group bonded to a carbonyl group. 3 ethanal or acetaldehyde methanal or formaldehyde 3 2 propanal or propionaldehyde 42

43 Aldehydes and Ketones Ketones have two organic groups bonded to a carbonyl group propanone or acetone 3 2-butanone or ethylmethylketone pentanone or diethylketone 43

44 Aldehydes and Ketones ommon names for aldehydes are derived from the name of the acid with the same number of atoms. IUPA names are derived from the parent hydrocarbon name by replacing -e with -al pentanal or pentyl aldehyde ,3-dimethylproponal or 2,3-dimethylpropionaldehyde 44 benzanal or benzyl aldehyde

45 Aldehydes and Ketones The IUPA name for a ketone is the characteristic stem for the parent hydrocarbon plus the suffix -one. A numeric prefix indicates the position of the carbonyl group in a chain or on a ring hexanone or methyl pentyl ketone 3-hexanone or ethyl propyl ketone acetophenone or methyl phenyl ketone 45

46 Amines Amines are derivatives of ammonia in which one or more atoms have been replaced by organic groups (aliphatic or aromatic or a mixture of both). There are three classes of amines. N 3 N 3 N 3 3 N 3 3 ammonia primary amine secondary amine tertiary amine 46

47 arboxylic Acids arboxylic acids contain the carboxyl functional group. 47

48 arboxylic Acids IUPA names for a carboxylic acid are derived from the name of the parent hydrocarbon. The final -e is dropped from the name of the parent hydrocarbon The suffix -oic is added followed by the word acid. Many organic acids are called by their common (trivial) names which are derived from Greek or Latin. 48

49 arboxylic Acids methanoic acid or formic acid 3 ethanoic acid or acetic acid propanoic acid or propionic acid butanoic acid or butyric acid 49

50 Esters Esters are usually called by their common names. Many simple esters occur naturally and have pleasant odors. Esters are frequently used in fragrances and as artificial 3 2 flavors ethyl butanoate or ethyl butyrate odor of pineapples octyl ethanoate or octyl acetate odor of oranges 50

51 Amides Amides are derivatives of organic acids and primary or secondary amines. The functional groups of amides are: R1 N or R1 N R2 or R1 N R2 R3 51

52 Some Derivatives of arboxylic Acids Amides are also named as derivatives of carboxylic acids. The suffix -amide is substituted for -ic acid or -oic acid. 3 N N 2 ethanamide or acetamide benzamide 52

53 verview of Functional Groups 53

54 verview of Functional Groups 54

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