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1、1Chapter 11 Introduction to Organic Chemistry: Alkanes11.1 Organic CompoundsCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 2Organic CompoundsAn organic compound Is a compound made from carbon atoms.Has one or more C atoms. Has many H atoms.May also contain O, S, N, P, and

2、halogens.3Elements in Organic CompoundsIn organic molecules, C atoms form bondsMostly with H and other C atoms.Sometimes atoms of O, N, S, P and halogens F, Cl, and Br.TABLE 11.8Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 4Organic vs. InorganicPropane, C3H8, is an organ

3、ic compound used as a fuel.NaCl, salt, is an inorganic compound composed of Na+ and Cl ions. Why is propane anorganic compound, butNaCl is not?Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 5Organic Compounds with More Carbon Atoms In organic molecules with more carbon ato

4、ms, Valence electrons are shared.Covalent bonds form between carbon and carbon atoms.Covalent bonds form between carbon and hydrogen atoms. H H H H H C C HH C C H H H H Hethane, CH3CH36Chapter 11 Introduction to Organic Chemistry: Alkanes11.2 AlkanesCopyright 2007 by Pearson Education, Inc. Publishi

5、ng as Benjamin Cummings 7AlkanesAlkanes contain only single carbon-carbon bonds (not double or triple)The names of alkanes Are determined by the IUPAC (International Union of Pure and Applied Chemistry) system.Use a prefix to indicate the number of carbons in a chain.End in ane.8IUPAC Names for Alka

6、nesCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings TABLE 11.29Structural FormulasAlkanes are written with structural formulas that areExpanded to show each bond.Condensed to show each carbon atom and its attached hydrogen atoms. Line to show bonds as lines and omit hydrogen

7、s 10Expanded and Condensed StructuresTABLE 11.3Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 11Line-Bond FormulasBecause each C atom has a tetrahedral arrangement, the order of atoms is not a straight line, but a zigzag pattern.A line-bond formula abbreviates the carbon a

8、toms and shows only the zigzag pattern of bonds from carbon atom to carbon atom.12ConformationsThe groups attached to a C-C single bond Rotate around the bond,Give different relative arrangements called conformations. Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings13Some St

9、ructures for ButaneTABLE 11.3Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 14CycloalkanesCycloalkanesHave 2H fewer than the open chain.Are named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.15CycloalkanesThe structura

10、l formulas of cycloalkanes are usually represented by geometric figures,Cyclopropane CH2 CH2 CH2CyclobutaneCH2 CH2CH2 CH216More CycloalkanesCyclopentane CH2 CH2 CH2CH2 CH2Cyclohexane CH2CH2 CH2CH2 CH2 CH217CycloalkanesCyclopropane and cyclobutane are slightly unstable and relatively rare in nature (

11、bad bond angle)Cyclopentane and cyclohexane are very stable and highly common in nature (good bond angle)Carbon wants 109.5 degrees bond angle18Chapter 11 Introduction to Organic Chemistry: Alkanes11.3 Alkanes with Substituents Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cumming

12、s 19Groups and SubstituentsOrganic molecules often have two parts:The base structure (generally a ring or chain)The groups (also known as substituents) which are attached to this base structure20IsomersIsomersHave the same molecular formula.Have different atom arrangements.Isomers of C4H10 Copyright

13、 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings branch21Alkyl groups Alkyl groups areAlkanes that are missing one H. Substituents attached to carbon chains or rings.Named with a yl ending. HH C CH3methyl H H H H C C CH3CH2ethyl H H22Naming SubstituentsIn the IUPAC system,A carbon br

14、anch is named as an alkyl group.Halogen atoms are named as halo.TABLE 11.5Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 23Alkanes with Alkyl Groups CH3CH3 CH CH3 methylpropanemethyl groups CH3 CH3CH3 CH CH2 CH CH3 2,4-dimethylpentane24Naming Alkanes with SubstituentsCopyr

15、ight 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 25Guide to Naming AlkanesGive the name of CH3 CH3 CH3CHCHCH3STEP 1 Longest chain is butane. STEP 2 Number chain. CH3 CH3 CH3CHCHCH3 1 2 3 4STEP 3 Locate substituents and name. 2,3-dimethylbutane26Learning CheckWrite the IUPAC name

16、for Cl CH3 CH3CH2CHCHCH327SolutionSTEP 1 Longest chain is pentane.STEP 2 Number chain from end that give the lowest numbers in the name. Cl CH3 (nearest end) CH3CH2CHCHCH3 5 4 3 2 1STEP 3 Locate substituents and name alphabetically. 3-chloro-2-methylpentane28Drawing Alkane StructuresCopyright 2007 b

17、y Pearson Education, Inc. Publishing as Benjamin Cummings 29What is In A Name?The structural formula is drawn from the IUPAC name.2, 4-dimethylhexane2, 4 dimethyl hexaneLocation of Two CH3- groups 6 carbon main chainbranches on attachedwith single C-C bondsmain chain30Learning CheckDraw the condense

18、d structural formula for 2-bromo-4-chlorobutane. Subquestion! What mistake did the textbook writers make in this problem?31SolutionSTEP 1 Longest chain has 4 carbon atoms.CCCCSTEP 2 Number chain and add substituents. Br C C C C Cl 1 2 3 4STEP 3 Add hydrogen to complete 4 bonds to each C. Br CH3CHCH2

19、CH2Cl32Naming Cycloalkanes with SubstituentsThe name of a substituent is placed in front of thecycloalkane name. CH3methylcyclobutane Number ring with two substituents1-bromo-2-chlorocyclopentane Br Cl33Learning CheckName each of the following: 1. CH3 CH2CH32. Cl34SolutionName each of the following:

20、 1. methylcyclopropane2. 1-chloro-3-ethylcyclohexane 35Write three isomers of C5H12 and name each.Learning Check36A chain of 5 carbon atoms CH3CH2CH2CH2CH3 pentaneA chain of 4 carbon atoms and 1 carbon branch CH3 CH3CHCH2CH3 2-methylbutaneA chain of 3 carbon atoms and 2 carbon branches CH3 CH3CCH3 2

21、,2-dimethylpropane CH3Solution37Chapter 11 Introduction to Organic Chemistry: Alkanes11.4 Properties of AlkanesCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 38Some Properties of AlkanesThe properties of alkanes includebeingNonpolar.Insoluble in water.Less dense than water

22、Flammable in air.Relatively unreactive.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 39Alkanes with 1-4 Carbon Atoms Alkanes with 1-4 carbon atoms areMethane, ethane, propane, and butane.Gases at room temperature.Used as heating fuels.Copyright 2007 by Pearson Education,

23、Inc. Publishing as Benjamin Cummings 40Alkanes with 5-17 Carbon Atoms Alkanes with 5-8 carbon atoms areLiquids at room temperature.Pentane, hexane, heptane, and octane.Very volatile.Used to make gasoline.Alkanes with 9-17 carbon atoms Are liquids at room temperatureHave higher boiling points.Are fou

24、nd in kerosene, diesel, and jet fuels.41Alkanes with 18 or more Carbon Atoms Alkanes with 18 or more carbon atomsHave high molar masses.Are waxy solids at room temperature.Used in waxy coatings of fruits and vegetables.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 42Crude

25、 OilThe hydrocarbons incrude oil areSeparated by boiling points.Heated to higher temperatures to produce gases that can be removed and cooled.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 43Combustion of AlkanesAlkanes Undergo combustion by reacting with oxygen to produce

26、 carbon dioxide, water, and energy. Are typically not very reactive due to strong C-C single bonds. alkane + O2 CO2 + H2O + energyCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 44Write the equationC5H12 + O2 CO2 + H2OBalance C C5H12 + O2 5CO2 + H2OBalance H C5H12 + O2 5CO2

27、 + 6H2OBalance O with O2 C5H12 + 8O2 5CO2 + 6H2O balancedBalancing A Combustion Equation45Classification of Carbon AtomsThe classification of carbon atoms indicates the number of carbon atoms attached.A primary carbon (1) bonds to one carbon atom.A secondary carbon (2) bonds to two carbon atoms.A te

28、rtiary carbon (3) bonds to three carbon atoms. CH3 |CH3 CH2CH2CH3 CH3CHCH3primary secondary tertiary46Free Radical HalogenationWhen alkanes react with halogens:One or more hydrogens will be replaced with halogensHalogens prefer to go to the more substituted (location with more surrounding carbons) l

29、ocationTertiary is more reactive than secondary which is more reactive than primaryLight or heat is required to form the radicalsRadicals have unpaired electrons and violate the octet rule (reactive)47Free Radical HalogenationSome examples of free radical halogenation:48Free Radical Halogenation Mec

30、hanism49Predicting the Major Product of Free Radical HalogenationHalogens prefer more substituted location on moleculeTertiary is more reactive than secondary which is more reactive than primaryReactivity depends on ease of forming radicalBelow radicals listed from easiest to form to hardest50Predic

31、t the Major Product51Predict the Major Product52Chapter 11 Organic Chemistry11.5 Functional GroupsCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 53Functional groups areAttached to the main chain or ring of an organic molecule. Used to classify types of organic molecules.Co

32、mpounds with similar functional groups often have similar properties.Functional Groups54Some Functional Groups Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings TABLE 11.955Alkenes and AlkynesAlkenes contain a double bond between adjacent carbon atoms.Alkynes contain a triple

33、 bond.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 56Alcohols and EthersAn alcohol contains the hydroxyl (-OH) functional group.In an ether, an oxygen atom is bonded to two carbon atoms COC . Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 57Mor

34、e Functional GroupsCopyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 58Aldehydes and KetonesAn aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom, attached to at least one hydrogen.In a ketone, the carbon of the carbonyl grou

35、p is attached to two other carbon atoms.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 59Carboxylic Acids and EstersCarboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group. O COHAn ester contains the carboxyl group between carbon

36、 atoms.Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 60Amines and AmidesIn amines, the functional group is a nitrogen atom. | N In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group.Copyright 2007 by Pearson Education, Inc. Publishing as Benja

37、min Cummings 61Functional Groups in Everyday Items Methyl amine (fish)Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings62Learning CheckClassify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine.1)CH3CH2CH2OH2) CH3OCH2CH33) CH3CH2NH2 O

38、 O | | 4) CH3COH 5) CH3COCH363SolutionClassify each of the following as alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine.1)CH3CH2CH2OH 2) CH3OCH2CH3 alcohol ether3) CH3CH2NH2 amine O O | | 4) CH3COH 5) CH3COCH3 carboxylic acid ester64Classification of Organic ReactionsMost organic reactions fit into one of three types:Substitution - one atom or group on a molecu