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New Way Chemistry for Hong Kong A-Level Book 3A1 Systematic Nomenclature 26.1Nomenclature of Hydrocarbons 26.2Nomenclature of the Derivatives of Hydrocarbons.

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Presentation on theme: "New Way Chemistry for Hong Kong A-Level Book 3A1 Systematic Nomenclature 26.1Nomenclature of Hydrocarbons 26.2Nomenclature of the Derivatives of Hydrocarbons."— Presentation transcript:

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2 New Way Chemistry for Hong Kong A-Level Book 3A1 Systematic Nomenclature 26.1Nomenclature of Hydrocarbons 26.2Nomenclature of the Derivatives of Hydrocarbons 26.3Nomenclature of the Derivatives of Aromatic Hydrocarbons Chapter 26

3 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.34) Nomenclature: naming of compounds The formal system of nomenclature is proposed by the International Union of Pure and Applied Chemistry (IUPAC) Fundamental principle of IUPAC system of nomenclature: Each different compound should have a different name.

4 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.35) Number of carbon atoms Stem name Number of carbon atoms Stem name Meth- Eth- Prop- But- Pent Hex- Hept- Oct- Non- Dec- Straight-Chain Acyclic Hydrocarbons 1.The naming of organic compounds is based on the parent hydrocarbon they derived from. The number of carbon atoms in hydrocarbons is represented by stem names.

5 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.35) Condensed structural formula Name CH 4 CH 3 CH 3 CH 2 CH 3 CH 3 (CH 2 ) 2 CH 3 CH 3 (CH 2 ) 3 CH 3 CH 3 (CH 2 ) 4 CH 3 CH 3 (CH 2 ) 5 CH 3 CH 3 (CH 2 ) 6 CH 3 CH 3 (CH 2 ) 7 CH 3 CH 3 (CH 2 ) 8 CH 3 Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane 2.(a) The suffix ‘ane’ is used for saturated hydrocarbons.

6 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.36) (b)The suffix ‘ene’ is used for unsaturated hydrocarbons with a double bond. e.g.CH 2 = CH 2 ethene CH 3 CH = CH 2 propene (c)The suffix ‘yne’ is used for unsaturated hydrocarbons with a triple bond. e.g.CH  CHethyne CH 3 CH  CHpropyne

7 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.36) 3.The lowest possible number is assigned to the carbon atoms of the multiple bond. The number is written before the suffix to indicate the position of the carbon atom of the multiple bond e.g.CH 3 CH 2 CH = CH 2 but-1-ene (not but-3-ene) CH 3 C  CCH 2 CH 3 pent-2-yne (not pent-3-yne)

8 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.36) 4.If a compound contains more than one double or triple bond, the prefixes like ‘di-’, ‘tri-’, are used to indicate its number of occurrence. An ‘a’ is added to the corresponding stem name. e.g. CH 3 CH 2 CH = CHCH = CH 2 hexa-1,3-diene 5.If a double or triple bond is not named in the ending of a name, the suffix ‘-en-’ and ‘-yn-’ are used respectively in the name. e.g. CH 2 = CHOHethenol

9 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.36) 6.The geometric isomers of an alkene are specified by the word of ‘cis-’ or ‘trans-’ before their names. e.g.

10 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.36) Branched-Chain Acyclic Hydrocarbons 1.Select and name the parent hydrocarbon (a)For saturated hydrocarbons, Parent chain: longest possible straight chain branched chain: all remaining e.g,

11 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.37) (b)For unsaturated hydrocarbons, Parent chain: longest possible straight chain which contains the maximum number of multiple bonds (c)The parent hydrocarbon is named as described in the naming of straight-chain acyclic hydrocarbons

12 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.37) 2.Name the branched chains (a)The number of carbon atoms in a branched chain is indicated by the stem names (b)The suffix ‘-yl’ is added to the corresponding stem names for branched chains containing only single bonds. e.g.– CH 3 methyl – CH 2 CH 2 CH 3 propyl – CH 2 (CH 2 ) 2 CH 3 butyl

13 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.37) 3.Numbering carbon atoms in the parent hydrocarbon (a)For saturated hydrocarbons, the parent hydrocarbon is numbered beginning with the end of the chain nearer the branched chain. e.g.

14 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.37) 3.(b)For unsaturated hydrocarbons, the parent hydrocarbon is numbered so as to include both carbon atoms of the double or triple bond. The numbering begins with the end of the chain nearer the double or triple bond. e.g.

15 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.38) 4.Use the numbers to designate the position of the branched chain. The parent name is placed last, and the branched chain, preceded by the number designating its position on the parent chain, is placed first. e.g.

16 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.38) 5.When two or more branched chains are present, a number corresponding to its position on the parent hydrocarbon is given to each branched chain so as to give the lowest possible numbers to the branched chains. The branched chains are listed alphabetically (i.e. ethyl before methyl). Multiplying prefixes such as ‘di’ and ‘tri’ are ignored when deciding the alphabetical order. e.g.

17 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.38) 6.When two branched chains are present on the same carbon atom, use that number twice. e.g.

18 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.39) 7.When two or more branched chains are identical, indicate this by the use of the prefixes ‘di-’, ‘tri-’, ‘tetra-’, and so on. Commas are used to separate numbers from each other. e.g.

19 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.39) Cyclic Hydrocarbons Simple cyclic hydrocarbons are named by adding prefix ‘cyclo-’ to the names of their corresponding acyclic counterparts. e.g.

20 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.39) Aromatic Hydrocarbons 1.Some aromatic hydrocarbons possess specific names.

21 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Hydrocarbons (SB p.39) 2.In substituted benzenes, the benzene ring is numbered so as to give the lowest possible numbers to the substituents. When more than two substituents are present and the substituents are different, they are listed in alphabetical order. e.g.

22 New Way Chemistry for Hong Kong A-Level Book 3A21 Example 26-1 Give the structural formula for each of the following compounds: (a)2-methylbutane (b)2,2,3-trimethylpentane (c)3-ethyl-2-methylhexane (d)3-methylbut-1-ene (e)2-propylpent-1-ene (f)3-ethylhex-1-yne (g)1,2-dimethylbenzene (h)cyclopentane 26.1 Nomenclature of Hydrocarbons (SB p.40) Answer

23 New Way Chemistry for Hong Kong A-Level Book 3A22 Solution: (a)(b) (c)(d) 26.1 Nomenclature of Hydrocarbons (SB p.40)

24 New Way Chemistry for Hong Kong A-Level Book 3A23 Solution: (e)(f) (g)(h) 26.1 Nomenclature of Hydrocarbons (SB p.40)

25 New Way Chemistry for Hong Kong A-Level Book 3A24 Check Point 26-1 Give the IUPAC name for each of the following compounds: (a)(b) (c)(d)(e) Answer 26.1 Nomenclature of Hydrocarbons (SB p.41) (a)Dimethylpropane (b)2,4-Dimethylhex-2-ene (c)3-Methylpent-1-yne (d)1-Methylcyclohexene (e)Ethylbenzene

26 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of the Derivatives of Hydrocarbons (SB p.41) Nomenclature of Compounds with One Type of Functional Group Compounds with functional groups that must be designated as prefixes fluoro- chloro- bromo- iodo- alkoxy- (e.g. methoxy-) azo- nitro- methyl phenyl — F — Cl — Br — I — OR — N = N — — NO 2 e.g. — CH 3 fluoride chloride bromide iodide ether azo nitro alky or aryl substituents PrefixFormulaGroup

27 New Way Chemistry for Hong Kong A-Level Book 3A26 1.The carbon chains are named and numbered in the usual way. Numbers are assigned to functional groups in the same way as the alkyl substituents. e.g Nomenclature of the Derivatives of Hydrocarbons (SB p.42)

28 New Way Chemistry for Hong Kong A-Level Book 3A27 2.When the parent chain has both alkyl groups and other substituents, the chain is numbered from the end nearer the first substituent, regardless of what substituents are. All the prefixes are then arranged in alphabetical order. e.g Nomenclature of the Derivatives of Hydrocarbons (SB p.42)

29 New Way Chemistry for Hong Kong A-Level Book 3A28 3.When two or more substituents are identical, indicate this by the use of the prefixes ‘di-’, ‘tri-’, ‘tetra-’, and so on. e.g Nomenclature of the Derivatives of Hydrocarbons (SB p.43)

30 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.43) Compounds with functional groups that may be designated as prefixes or suffixes alkanamide-amideRCONH 2 Amide alkanoyl chloride-oyl chlorideROClAcyl chloride alkyl alkanoate-oateRCO 2 R’Ester alkanoic acid-oic acidRCO 2 HCarboxylic acid Structural formula Systematic nameSuffix General formula Group

31 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.43) alkanal-alRCHOAldehyde alkanol-olROHAlcohol alkanone-oneRCOR’Ketone Structural formula Systematic nameSuffix General formula Group Compounds with functional groups that may be designated as prefixes or suffixes

32 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.44) Principal functional group is the functional group expressed as a suffix and has priority over unsaturated centres. Parent carbon chain is chosen to include the longest possible carbon chain and maximum number of principal functional groups. The carbon chain is numbered to give the principal functional group the lower number. The position of the principal functional group is indicated by using this number, and the positions of other substituents are indicated by using the numbers corresponding to their positions along the parent carbon chain.

33 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.44) 1.Alcohols (ending ‘-ol’)

34 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.44) 2.Aldehydes (ending ‘-al’) and ketones (ending ‘-one’) The carbon atom of the carbonyl group (i.e.) is included in the parent carbon chain.

35 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.45) 3.Carboxylic acids (ending ‘-oic acid’) The carbon atom of the carboxyl group (i.e.) is included in the parent carbon chain.

36 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.45) 4.Acyl chlorides (ending ‘-yl chloride’) The carbon atom of the group is included in the parent carbon chain.

37 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.45) 5.Amides (ending ‘-amide’) The carbon atom of the amide group (i.e.) is included in the parent carbon chain. Alkyl groups on the nitrogen atom of amides are named as substituents and the named substituent is preceded by N- or N,N-.

38 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.45) 6.Ester (ending ‘-oate’) The name of ester is derived from the names of the alcohol (with the ending ‘-yl’) and the carboxylic acid (with the ending ‘-oate’) forming the ester. The portion of the name derived from the alcohol comes first, and then the carboxylic acid.

39 New Way Chemistry for Hong Kong A-Level Book 3A38 Example 26-2 Give the structural formula for each of the following compounds: (a)2-methylhexane (b)4-methylheptan-2-ol (c)pentan-2-one (d)5-methylhexanoic acid (e)methyl 2,2-dimethylpentanoate (f)N-ethyl-N-propylethanamide Answer 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.46)

40 New Way Chemistry for Hong Kong A-Level Book 3A39 Solution: (a)(b) (c)(d) 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.46)

41 New Way Chemistry for Hong Kong A-Level Book 3A40 Solution: (e)(f) 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.46)

42 New Way Chemistry for Hong Kong A-Level Book 3A41 Check Point 26-2 Give the IUPAC name for each of the following compounds: (a)(b) (c)(d) Answer 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.46) (a)3,4-Dimethylpentanoic acid (b)Pentan-2-ol (c)3,4-Dimethylhexanal (d)N,N-Dimethylpropanamide

43 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.47) Nomenclature of Compounds with More than One Type of Functional Group 1.Only one of the functional groups can be designated as the ending of the name. This is the principal functional group. The priority of choosing principal functional group in decreasing order is listed in the following table. The group that is highest in the list precedes all other groups and become the principal functional group in the compound to be named.

44 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.47) GroupFormulaPrefixSuffix Carboxylic acidcarboxy-oic acid Sulphonic acidsulpho-sulphonic acid Ester—-oate Acyl halide—-oyl halide Amide—-amide

45 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.47) GroupFormulaPrefixSuffix Nitrilecyano-nitrile Aldehydeoxo-al Ketoneoxo-one Alcoholhydroxy-ol Amineamino-amine

46 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.48) 2.The principal functional group has priority in the selection of the longest possible carbon chain and the choice of lowest number. Other groups are designated as prefixes and listed in alphabetical order.

47 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.48) Example 1: Principal functional group: Parent chain: 4-chloro-4-methylpentanal

48 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.48) Example 2: Principal functional group: Parent chain: 2-bromo-3-methylbut-2-enoic acid

49 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.49) Example 3: Principal functional group: Parent chain: 3-chloro-2-iodobutanamide

50 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.49) Example 4: Principal functional group: Parent chain: 3,4-dichloro-5-hydroxy-4-methylpentan-2-one

51 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Hydrocarbons (SB p.50) Example 5: Principal functional group: Parent chain: 4-amino-2-phenylhexanal

52 New Way Chemistry for Hong Kong A-Level Book 3A51 Example 26-3 Give the structural formula for each of the following compounds: (a)3-oxobutanoic acid (b)5-hydroxypentanal (c)2-hydroxy-4-oxohexanal (d)1,8-dihydroxyoctan-3-one Answer 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.51) Solution: (a)(b) (c)(d)

53 New Way Chemistry for Hong Kong A-Level Book 3A52 Example 26-4 A student has given the wrong names for the following organic compounds. Given the structural formulae and the correct names for these compounds. (a)3-hydroxy-3-ethylbutanoic acid (b)2-chloro-3-cyano-1-methylpropane (c)propoxyethane Answer 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.51) Solution: (a) 3-Hydroxy-3-methylpentanoic acid

54 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of the Derivatives of Hydrocarbons (SB p.52) Solution: (b) 3-Chloropentanenitrile (c) Ethoxypropane

55 New Way Chemistry for Hong Kong A-Level Book 3A54 Check Point 26-3 Give the IUPAC name for each of the following compounds: (a)(b) (c)(d) Answer 26.2 Nomenclature of the Derivatives of Hydrocarbons (SB p.52) (a)3-Chlorobutanone (b)1-Ethoxyethanol (c)2-Amino-3-hydroxypentanoic acid (d)4-Hydroxy-2-methylpentanamide

56 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.53) Monosubstituted Aromatic Hydrocarbons 1.Some monosubstituted aromatic hydrocarbons can be named by adding the name of the substituents as prefixes to the name of the aromatic hydrocarbon. e.g.

57 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.53) 2.For other monosubstituted aromatic hydrocarbons, the substituent and the benzene ring taken together may form a new parent name. e.g.

58 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.53)

59 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.54) Polysubstituted Aromatic Hydrocarbons 1.When two or more substituents are identical, indicate this by the use of the prefixes ‘di-’, ‘tri-’, ‘tetra-’ and so on. The benzene ring is numbered so as to give the lowest possible numbers to the substituents. e.g.

60 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.54) 2.When the substituents are different, they are listed in alphabetical order. e.g.

61 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of Derivatives of Aromatic Hydrocarbons (SB p.54) 3.When a substituent is one that when taken together with the benzene ring to give a new parent name, that substituent is assumed to be in position 1 and the new parent name is used. e.g.

62 New Way Chemistry for Hong Kong A-Level Book 3A61 Example 26-5 Give the structural formula for each of the following compounds: (a)1,4-dichlorobenzene (b)3-nitrobenzoic acid (c)4-bromotoluene (d)3,5-dinitrophenol Answer 26.3 Nomenclature of the Derivatives of Aromatic Hydrocarbons (SB p.55) Solution: (a)(b) (c)(d)

63 New Way Chemistry for Hong Kong A-Level Book 3A Nomenclature of the Derivatives of Aromatic Hydrocarbons (SB p.51) Check Point 26-4 Give the IUPAC name for each of the following compounds: (a)(b) (c)(d) Answer (a)2-Bromo-1,4-dichlorobenzene (b)5-Bromo-2-chlorobenzoic acid (c)2,4-Difluorobenzenesulphonic acid (d)4-Hydroxybenzoic acid

64 New Way Chemistry for Hong Kong A-Level Book 3A63 The END


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