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1. NOMENCLATURE OF ORGANIC COMPOUNDS BY Namile .SHYAM PRASAD 2. INTRODUCTION Carbon is special because a single carbon atom is capable of combining with up to four…
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  • 1. NOMENCLATURE OF ORGANIC COMPOUNDS BY Namile .SHYAM PRASAD
  • 2. INTRODUCTION Carbon is special because a single carbon atom is capable of combining with up to four other atoms (valence of four = maximum of four bonds). Carbon can combine with many other carbon atoms making large molecules. This means that carbon atoms can form chains and rings onto which other atoms can be attached. In Chemistry, an organic compound is one carbon atoms containing.
  • 3. Chains of Carbon Atoms The simplest Organic compounds are made up of only carbon and hydrogen atoms only and are called hydrocarbons. Names of simple chains of hydrocarbons are given names based on the number of carbon atoms in the molecule. Prefixes are used to denote the number carbon atoms. Alkane hydrocarbons consist of carbon and hydrogen atoms linked together with single bonds.
  • 4. CLASSIFICATION OF ORGANIC COMPOUNDS Open chain compounds or acyclic compounds Closed chain or ring compounds or cyclic compounds Saturated or Unsaturated Homocyclic or carbocyclic Heterocyclic Alicylic OR Aromatic Benzenoid Non-benzenoid
  • 5. Aliphatic compounds: open-chain compounds and ring compounds that are chemically similar to open-chain compounds. Alkanes, alkenes, alkynes, dienes, alicyclics, etc. Aromatic compounds: unsaturated ring compounds that are far more stable than they should be and resist the addition reactions typical of unsaturated aliphatic compounds. Benzene and related compounds.
  • 6. 6 Six Step Process 1) Find the longest carbon chain 2) Name it 3) Determine any ending 4) Number the carbon atoms 5) Separate and name side/substituent groups 6) List side/substituent groups alphabetically
  • 7. IUPAC Rules for NomenclatureIUPAC Rules for Nomenclature  1.1. Find and name the longest continuous carbon chain. This is calledFind and name the longest continuous carbon chain. This is called thethe parent chainparent chain.. 2.2. Number the chain consecutively, starting at the end nearest anNumber the chain consecutively, starting at the end nearest an attached group)attached group) 3.3. Identify and name groups attached to this chain.Identify and name groups attached to this chain. 4.4. Designate the location of each substituent group with the number ofDesignate the location of each substituent group with the number of the carbon parent chain on which the group is attached. Place a dashthe carbon parent chain on which the group is attached. Place a dash between numbers and letters.between numbers and letters. 5.5. Assemble the name, listing groups in alphabetical order.Assemble the name, listing groups in alphabetical order. The prefixes di, tri, tetra etc., used to designate several groupsThe prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when alphabetizing. Place aof the same kind, are not considered when alphabetizing. Place a comma between multiple numbers.comma between multiple numbers.
  • 8. Step 1: Find the longest carbon chain Find the longest, uninterrupted, continuous carbon chain. It is not required that in the picture or drawing of the carbon chain that atoms all are in line only that it is the longest continuous carbon chain
  • 9. Step 2: Name it Butane Ethane Octane Count the number of carbons in the chain and select the appropriate root name based on the number of carbon atoms on the chain
  • 10. Step 3: Determine any ending Butane Ethanol Octane Determine if any ending needs to be added to the base name This is determined by the presence of a functional group on any of the carbon atoms A list of functional groups and their structure can be found on next slide
  • 11. Priority of functional groups •Decreasing priority of the functional group —COOH, —SO3H, —COOR, —COCl, —CONH2, —CN, —CHO, >CO, —OH, —NH2, >C=C<, —C≡C—. If more than one functional group is present then we decide the the parent functional group on the basis of the following priority basis.
  • 12. Step 4: Number the carbon atoms Butane 1 2 3 4 1 2 Octane 3 4 5 6 7 8 Ethanol 12 •Start at both ends of the carbon chain, naming the first carbon 1, the next and so on •Find which end leads to or arrives at a side group first •That end then becomes the carbon 1 end •Number each carbon continuously through to the other end of the main chain starting with 1
  • 13. C methane C-C ethane C-C-C propane C-C-C-C butane C-C-C-C-C pentane C-C-C-C-C-C hexane C-C-C-C-C-C-C heptane I. Alkane Hydrocarbons
  • 14. C-C-C-C-C-C-C-C octane C-C-C-C-C-C-C-C-C nonane C-C-C-C-C-C-C-C-C-C decane C-C-C-C-C-C-C-C-C-C-C undecane C-C-C-C-C-C-C-C-C-C-C-C dodecane Alkane Hydrocarbans
  • 15. Prefixes for of CarbonsPrefixes for of Carbons S.NO 11 PRIFIXPRIFIX METMET 66 HexHex 22 EthEth 77 HeptHept 33 PropProp 88 OctOct 44 ButBut 99 NonNon 55 PentPent 1010 DecDec
  • 16. Types of Carbon AtomsTypes of Carbon Atoms • Primary carbon (1Primary carbon (1oo )) – a carbon bonded toa carbon bonded to one other carbonone other carbon • Secondary carbon (2Secondary carbon (2oo )) – a carbon bonded toa carbon bonded to two other carbonstwo other carbons • Tertiary carbon (3Tertiary carbon (3oo )) – aa carbon bonded tocarbon bonded to three other carbonsthree other carbons C C C H H H C C H C C C C H H C C H H C C H C C C C H H C C H H C C C H C C C H H H C C H
  • 17. 17 Step 4: Number the carbon atoms  If both ends of the chain come to a side group with the same number of carbons, then the side with the more complex group (contains more atoms) becomes the end that receives the label on its end carbon – If that also is a tie then the next tie breaker is alphabetizing the side groups – The higher order or first occurring alphabetical character side group becomes carbon 123456
  • 18. 18 Some Substituent Groups
  • 19. 19 Step 5: Separate and name substituent groups • Separate out and individually name all the substituent side groups or chains, sometimes referred to as pendent groups • The common names for side groups are – Cl = chloro – F = fluoro – Br = bromo – OH = hydroxy – NH2 = amino – CN = cyano – NO2 = nitro Substituent group = Side group 1, 3 - dibromo - 2 - butanone
  • 20. 20 Step 6: List substituent chains in alphabetical order • The convention requires a parenthesis to be placed around the substituent chains or groups if it is more than a single atom or molecule • Commas are placed between numbers and dashes are placed between numbers and letters and in front of the parenthesis • A group of atoms appearing in the brackets is alphabetized by the real first letter of the group, whereas, normal convention does not treat the di’s or tri’s as part of the alphabetizing process
  • 21. IUPAC NOMENCLATURE OF SPIRO BYCYCLIC HYDROCARBONS  Spiro bicyclic contain two rings consisting of carbon atoms only and the two rings are linked by a common carbons,these compounds are named by placing prifix ‘spiro’ before the name of the acyclic parent  Hydrocarbon with same number of skelital carbon atoms, the number of skeltal atoms linked to the spiro at are indicated by arabic numbers ,seprately by afull stop  The numbers are written in ascending order and enclosed squre bractes numbering of spiro bicyclic hydrocarbon starts with a ring carbon next to the spiro atom and proceeds frist through the smaller ring and then through the spiro atom and around the secondary
  • 22. IUPAC NOMENCLATURE OF BRIDGED BYCYCLIC HYCARBONS  Saturated bicyclic system having two or more atoms in common are named by prefixing bicyclo to the name the cyclic parent hydrocarbon system containing the the total number of carbon atoms in the skleton  Then numbar of carbon atims in each of the three bridges connecting the two tertiary carbon atoms is indicated inarenthese in descending order and arabic numbers are used to indicate the number of carbon atoms and then numbers are seperated by full stops
  • 23. 23 Root Names Number of Carbon Atoms Root Name Number of Carbon Atoms Root Name 1 meth 11 undec 2 eth 12 dodec 3 prop 13 tridec 4 but 14 tetradec 5 pent 15 pentadec 6 hex 20 icos 7 hept 21 henicos
  • 24. Compound Class Ending Functional Group Alkanes -ane None Haloalkanes -ane ―X Alcohols -ol ―OH Ethers ether ―O― Alkenes -ene Alkynes -yne ―C≡C― Aldehydes -al Ketones -one Carboxylic Acids -oic acid Esters -oate Anhydrides anhydride Amides -ide Nitriles -ile ―C≡N Amines -amine
  • 25. Aldehydes and Ketones
  • 26. Nomenclature: Aldehydes, common names: Derived from the common names of carboxylic acids; drop –ic acid suffix and add –aldehyde. CH3 CH3CH2CH2CH=O CH3CHCH=O butyraldehyde isobutyraldehyde (α-methylpropionaldehyde)
  • 27. Aldehydes, IUPAC nomenclature: Parent chain = longest continuous carbon chain containing the carbonyl group; alkane, drop –e, add –al. CH3 CH3CH2CH2CH=O CH3CHCH=O butanal 2-methylpropanal H2C=O CH3CH=O methanal ethanal
  • 28. Ketones, common names: Special name: acetone “alkyl alkyl ketone” or “dialkyl ketone” H3C C CH3 O CH3CH2CCH3 O CH3CH2CCH2CH3 O ethyl methyl ketone diethyl ketone CH3CCH2CH2CH3 O methyl n-propyl ketone
  • 29. Ketones: IUPAC nomenclature: Parent = longest continuous carbon chain containing the carbonyl group. Alkane, drop –e, add –one. Prefix a locant for the position of the carbonyl using the principle of lower number. CH3CH2CCH3 O CH3CH2CCH2CH3 O 2-butanone 3-pentanone CH3CCH2CH2CH3 O 2-pentanone
  • 30. 30 Nomenclature of Ethers Common name - Name(s) of alkyl group(s) listed first followed by the word “ether”
  • 31. Chapter 2 31 Nomenclature of Ethers • IUPAC name - The smaller alkyl group is converted to an “alkoxy” name and used as a substituent
  • 32. Chapter 2 32 Nomenclature of Alcohols • Common name - Name of the Alkyl group followed by the word “alcohol”
  • 33. Chapter 2 33 Nomenclature of Alcohols • IUPAC name - The OH group is a site of reactivity (a functional group) Functional group is denoted by the suffix, “ol” CH3OH CH3CH2OH methanol ethanol
  • 34. Chapter 2 34 IUPAC Nomenclature of Alcohols • Parent Hydrocarbon is the longest continuous chain that contains the OH • Number the chain in direction that gives functional group the lowest number • If both a substituent and a functional group are present, the functional group gets the lower number
  • 35. 35 IUPAC Nomenclature of Alcohols • If the functional group gets the same number when counted from both directions, use direction which gives the substituent the lower number • If there is more than one substituent, cite substituents in alphabetical order
  • 36. 36 IUPAC Nomenclature of Alcohols • System is summarized as [Substituent] [Parent Hydrocarbon] [Functional Group]
  • 37. Aromatic compounds
  • 38. Nomenclature of Aromatic Compounds 1. Mono substituted Benzenes a. IUPAC name ClCH2CH3C(CH3)3 NO2 t-Butylbenzene Ethylbenzene Nitrobenzene Chlorobenzene CH2 Benzyl group C O OH CH=CH2 CH3 OH C O H Toluene Styrene Phenol Benzaldehyde Benzoic acid NH2 Aniline CH2 Cl Benzyl chloride b. Common name
  • 39. Thank you
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