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Fundamentals of General, Organic and Biological Chemistry 6th Edition Chapter Twelve Introduction to Organic Chemistry: Alkanes James E. Mayhugh Copyright © 2010 Pearson Education, Inc. 1 12.1 The Nature of Organic Molecules ► Organic chemistry: The study of carbon compounds. ► Carbon ALWAYS forms four bonds. 2 ► Carbon’s 4 bonds can be any combination of single, double and triple bonds 3 12.4 Drawing Organic Structures Condensed structure: A shorthand way of drawing structures in which C-C and C-H bonds are understood rather than shown. 4 12.4 Drawing Organic Structures Line structure: An even shorter notation: 5 12.2 Families of Organic Molecules: Functional Groups ► Organic compounds are put into families (categories) according to ►The types of atoms attached to the carbons ►The types of bonds between the carbons ►Single, double, triple 6 7 Organic Nomenclature ► Basic naming system (nomenclature): 8 Hydrocarbon Nomenclature ► The simplest group of Families are the hydrocarbons… compounds containing only carbon and hydrogen ►All carbon-carbon single bonds: alkanes ►At least one C=C double bond: alkenes ►At least one C C triple bond: alkynes 9 Hydrocarbon Nomenclature ► Hydrocarbons can be ►“straight” chain 10 Hydrocarbon Nomenclature ► Hydrocarbons can be ►“straight” chain ► branched chain 11 Hydrocarbon Nomenclature ► Hydrocarbons can be ►“straight” chain ► branched chain ► cyclic 12 12.6 Naming Alkanes ► Suffix: -ane ► Parent : based on # of Carbons in longest, continuous chain 13 1 carbon 2 carbons 3 carbons 4 carbons 5 carbons 6 carbons 7 carbons 8 carbons 9 carbons 10 carbons methethpropbutpenthexheptoctnondec14 12.6 Naming Alkanes ►Examples of “Straight chain” alkanes: CH3CH2CH3 15 ► Branched-chain alkanes (Rules are on following slides) 16 ► What is the chemical formula of this molecule? 17 ► Branched-chain alkanes (Rules are on following slides) 18 12.6 Naming Branched-Chain Alkanes ► Branched-chain alkanes have “substituents” branching off of the main chain. ► For hydrocarbons, these substituents (or “branches”) are also hydrocarbons ►# of carbons in branch: normal prefix ►Suffix of hydrocarbon branch: -yl ►Name must include WHICH carbon of the main chain the branch is connected to. 19 12.6 Naming Branched Alkanes ► STEP 1: Name the main chain (parent + suffix). Find the longest continuous chain of carbons! ► STEP 2: Number the carbon atoms in the main chain. Begin at the end nearer the first branch point ► STEP 3: Identify the branching substituents, and number each according to its point of attachment to the main chain ► STEP 4:Write the name as a single word, ►If two or more identical substituents are present, use one of the prefixes di-, tri-, tetra►If two or more different substituent groups are present, cite them in alphabetical order 20 21 12.9 Naming Cyclic Alkanes 22 12.9 Naming Cyclic Alkanes ► Naming rules are mostly the same as for other alkanes ► Additional Rules: ►The ring is ALWAYS the main chain ►The prefix “cyclo” is added to the name of the main chain ►If only 1 branch, it doesn’t need to be numbered ►If more than one branch, number the carbons in the ring to get the lowest combination of numbers of branch locations. 23 End of Chapter 12 24 Fundamentals of General, Organic and Biological Chemistry 6th Edition Chapter Thirteen Alkenes andAlkynes James E. Mayhugh Copyright © 2010 Pearson Education, Inc. Chapter Seven 25 13.2 Naming Alkenes and Alkynes (rules on following slides) 26 13.2 Naming Alkenes and Alkynes 27 13.2 Naming Alkenes and Alkynes 28 13.2 Naming Alkenes and Alkynes ► Very similar rules as for alkanes ► Additional rules: ►Choose longest chain that contains the double or triple bond ►Suffix for alkenes: -ene ►Suffix for alkynes: -yne ►Include a number with the parent to indicate which carbon the double/triple bond starts on. 29 ►3-methylcylclopentene 30 ► Cyclic alkene special rules ►Carbons 1 and 2 MUST go “through” the double bond ►If there is more than one double bond, number the ring to give the double bonds the lowest numbers… then worry about branches. 31 ►5-ethyl-1,3-cylclohexene 32 Isomers ► 2 or more molecules with the same number of each atom, but are connected differently. ► These molecules will have different names. 33 Isomers 34 End of Chapter 13 35 Fundamentals of General, Organic and Biological Chemistry 6th Edition Chapter Fourteen Some Compounds With Oxygen or a Halogen James E. Mayhugh Copyright © 2010 Pearson Education, Inc. Chapter Seven 36 14.1 Alcohols and Ethers ► An alcohol has an –OH covalently bonded to a carbon chain. ► These compounds are NOT basic. ► An ether has an O in the midst of a carbon chain. 37 14.3 Naming Alcohols (rules on following slides) 4-methyl-1-cyclohexanol 1-propanol methanol (only 3 carbons, not 4) 38 14.3 Naming Alcohols ► 1. Number the longest carbon chain starting at the end that gets you to the OH the quickest. ► 2. Suffix: replace the “e” at the end of the normal name for the main chain with “ol” ► 3. Denote location of the OH the same way you show the location of a double or triple bond ► 4. Name and slow location of any hydrocarbon branches. 39 14.8 Ethers Ethers are named by identifying the two carbon “branches” attached to the oxygen atom (in alph. order) and adding the word ether. 40 14.8 Ethers Butyl propyl ether 41 14.10 Halogen Containing Compounds 42 14.10 Halogen Containing Compounds ► Halogens: Fluorine, chlorine, bromine, iodine ►As a branch: fluoro, chloro, bromo, iodo ► Halogen branches are given “numbering preference” over hydrocarbon branches ►But NOT over any substituent that determines the family of the compound (like alcohols, double bonds, etc.) 43 End of Chapter 14 44 Fundamentals of General, Organic and Biological Chemistry 6th Edition Chapter Sixteen Aldehydes and Ketones James E. Mayhugh Copyright © 2010 Pearson Education, Inc. Chapter Seven 45 16.1 The C=O group ► Both aldehydes and ketones contain a C=O group ► They are NOT alkenes… alkenes have C=C bonds ► The difference between aldehydes and ketones is the placement of the C=O group. 46 16.2 Aldehydes CH3CHO 47 16.2 Aldehydes Propanal 3-methylbutanal CH3CHO Ethanal methanal (common name: formaldehyde) 48 16.1 Aldehydes ►Aldehydes: ►The Carbon of the C=O group is one of the end carbons ►Suffix: -al ►No need to show its number… it’s ALWAYS “1” if it’s an aldehyde. 49 16.2 Ketones CH3COCH2CH2CH3 (how can you know it’s not an ether??) 50 16.2 Ketones 2-butanone 4-methyl-3-hexanone CH3COCH2CH2CH3 (how can you know it’s not an ether??) 2-pentanone cyclohexanone 51 16.1 Ketones ►Ketones: ►The Carbon in the C=O group is one of the INTERIOR carbons ►Suffix: -one ►Location of the =O must be numbered (except for propanone and butanone) 52 End of Chapter 16 53 Fundamentals of General, Organic and Biological Chemistry 6th Edition Chapter Seventeen Carboxylic Acids James E. Mayhugh Copyright © 2010 Pearson Education, Inc. Chapter Seven 54 17.1 Carboxylic Acids ► Carboxylic acids look like a combination of an alcohol and an aldehyde … on the same carbon. 55 17.1 Carboxylic Acids methanoic acid (common name: formic acid) CH3CO2H ethanoic acid (common name: acetic acid) 56 17.3 Acidity of Carboxylic Acids Carboxylic acids are weak acids (ethanoic acid) 57 17.1 Carboxylic Acids ► Carboxylic acids ►Suffix: -oic acid ►No need to number the acid group… it has to be on an end carbon, so it is automatically “1-” propanoic acid 58 End of Chapter 17 59 It may be hard to believe, but… 60 61