Nomenclature Of Organic Compounds 2 03-07-12 - Kar
O Organic i chemistry h i Nomenclature of Organic compounds Bridge course
Nomenclature of organic compounds Th are two There t systems t off naming i 1 Trivial system 1. 2. IUPAC system y
Trivial system: When a few organic g compounds p were known,, they were named on the basis of their history or source. source Eg: HCOOH –Formic acid (red ants) CH3COOH‐Aceticacid COOH A ti id (acetum‐vinegar) ( t i )
IUPAC system: (International Union of Pure and Applied Chemistry) By using B i this thi system t one can name any complex organic compound easily. The name assigned to an organic compound p on the basis of latest IUPAC rules is known as systematic name.
W iti IUPAC name off a compound Writing d y The IUPAC name of the compound p built from 4 parts y Prefix y word root y primary suffix y secondary suffix
Prefix y It denotes the substituent group if p present in the organic g compound p Substituent group prefix ‐F Fluoro l ‐Cl Cl chloro ‐Br Bromo
substituent ‐I ‐NO2 NO2 ‐CH3 ‐C2H5 ‐C3H7 3 7 prefix Iodo Nitro Methyl Ethyl Propyl py
Word root y It indicates the number of carbon atoms in the longest possible chain. N off carbon No. b atoms 1 2 3 word d root meth‐ eth‐ prop‐
No.of carbon atoms Word root 4 but‐ 5 6 7 8 9 10 pent‐ hex‐ hept‐ p 0ct‐ non‐ dec‐
Primary Suffix yIt denote the nature of carbon to carbon bond compounds. yane: b d bond yene: bond yyne: bond in the organic
S Secondary d suffix ffi It represents the functional group if present in an organic molecule and is attached h d to the h primary i suffix ffi while hil writing the IUPAC name.
Class of compounds Alcohol Aldehydes Ketones Carboxylic acids Amines E t Esters functional group ‐OH ‐CHO C O ‐COOH COOH ‐NH2 ‐COOR COOR secondaryy suffix ‐ol ‐al ‐one ‐oic oic acid ‐amine ‐0ate t
Writing W ii IUPAC name off an aliphatic compound IUPAC prefix IUPAC fi (es) word ( ) d roott primary i suffix secondary suffix
Eg: g H3C 3 Word root root-:: prop CH 2 CH3 H2 C 1 OH Prefix -: methyl Pi Primary suffix-: ffi -ane Secondary suffix-: -ol IUPAC name- 2-Methyl-1-propanol (terminal ‘e’ of the p-suffix is dropped if the sec-suffix begins with ith a,e,i,o,u) i )
IUPAC rules for naming organic compounds 1.Longest chain rule: Select the longest continuous chain of carbon atoms known as “parent” chain 1 2 3 4 5 3 4 5 6 CH3-CH-CH2-CH2-CH3 CH3-CH-CH2-CH2-CH3 CH2-CH CH3 CH2-CH CH3 2 1 2-Ethylpentane 2 Ethylpentane 33-Methyl Methyl hexane (wrong) (correct)
2.Lowest number rule The carbon chain selected is numbered from the end nearest to the side chain or substituent so as to give the lowest number to the carbon carrying the side chain. 1 2 3 4 4 3 2 1 CH3-CH-CH2-CH3 CH3-CH-CH2-CH3 CH3 C CH3 C 2‐Methylbutane ( correct)) 3‐Methylbutane ( (wrong) )
Lowest sum rule: Where there are more than one substituent, numbering of the chain is done in such a way that the sum of the numbers assigned to the substituents is minimum. “The e te term Locant oca t iss used to de denote ote tthe e number u be indicating the substituent attached”. CH3 CH3 CH3 CH3 1 2 3 4 5 5 4 3 2 1 CH3-C-CH2-CH-CH3 CH3-CH-CH2-CH-CH3 CH3 CH3 2,2,4‐trimethylpentane 2,2,4 trimethylpentane 2,4,4‐trimethylpentane 2,4,4 trimethylpentane Set of locants 2 2 4 8 set of locants 2 4 4 10 (correct) (wrong)
3 Arrangement of Prefixes 3. If more than one group is attached to the carbon chain, these groups should be arranged alphabetically. When two or more identical substituents are present prefixes like di, tri, tetra, etc. are used. However these prefixes are not considered for alphabetical order. 1 2 3 4 5 6 CH3-CH-CH2-CH-CH2-CH3 CH3 CH CH2 CH CH2 CH3 CH3 CH2 CH3 2-Methyl-4-ethylhexane (wrong) 1 2 3 4 5 6 CH3-CH-CH2-CH-CH2-CH3 CH3 CH CH2 CH CH2 CH3 CH3 CH2 CH3 4-Ethyl-2-methylhexane (right)
y If two different groups are located at the equivalent positions, the h numbering b should h ld be b done d in such h a way that alkyl group which comes first in the alphabetical p order g gets the lowest p position. 1 2 3 4 5 6 CH3-CH C C 2-CH-CH-CH C C C 2-CH C 3 C2H5 CH3 3-Ethyl-4-methylhexane
4: Lowest Number to the Functional Group p y In case there is a functional group in a molecule, the parent chain is numbered such that the f functional ti l group gets t the th lowest l t number, b even if the lowest number rule is violeted. CH3 H3C 1 C 2 CH3 CH3 H2 C 3 H C 4 CH3 5 OH 2,2-Dimethylpentan-4-ol 2,2 Dimethylpentan 4 ol wrong H3C 5 C 4 CH3 H2 C 3 H C 2 CH3 1 OH 4,4-Dimethylpentan-2-ol , e y pe o Right
5 Presence of Identical groups If an organic molecule has more than one functional group, prefixes fi like lik di, di tri, i tetra are used d before b f the h suffix indicating the functional group. However, the ‘e’ e of the corresponding alkane is retained retained. 4 H3C 3 CH OH 2H C 1 CH2 OH OH Butane-1,2,3-triol 2 1 H2C CN H2C CN 4 3 Butane-1,4-dinitrile
Nomenclature of unsaturated hydro carbons a) H 3C 4 H2 C C H2 CH2 H3C 1 1 3 But-1-ene c) b) C C CH3 2 3 4 But-2-yne 5 4 3 2 1 H3C C H C H C H CH2 Penta-1,3-diene
IUPAC nomenclature of poly functional compound In case of polyfunctional compounds one of the functional group chosen as the principal group and d the th compound d is i named d on that basis.
The order of decreasing priority for functional groups g p Sulphonicacid carboxylic acid ester acid chloride amide nitrile aldehyde y ketone alcohol amine doublebond triple bond ether other substituents (X NO2 R) OHC H2 C H2 C H2 C COOH 4 3 2 1 principal functional group substituent group 4-Formylbutanoicacid
The IUPAC name of an alicyclic compounds is prefixed with “cyclo”. NO2 1 3 2 2 a)) b) c) 1 Cyclohexane y 3 3-Nitrocyclohexene y 1-Methyl-3-propylcyclohexane
Nomenclature of Aromatic compounds NH2 6 5 a) O2N Cl 1 2 4 3 1 b) NO2 CH3 6 2 5 3 4 C2H5 1-Chloro-2,4-dinitrobenzene 4-Ethyl-2-methylaniline
IUPAC names of organic compounds by b bond b d line li notation i b a But-2-ene 2,3-Dimethylbuta-1,3-diene d c 2,2-Dimethylbutane 3,3-Diethylpentane
THANK YOU BRIDGE COURSE‐2012
Class of functional secondary compounds group suffix . IUPAC rules for naming organic compounds 1.Longest chain rule: Select the longest continuous chain of carbon atoms known as "parent" chain 12345 3456 CH3-CH-CH2-CH2-CH3 CH3-CH-CH2-CH2-CH3
4.3 More complex nomenclature systems, 49 4.4 Coordination nomenclature, an additive nomenclature, 51 4.5 Substitutive nomenclature, 70 4.6 Functional class nomenclature, 96 5 ASPECTS OF THE NOMENCLATURE OF ORGANOMETALLIC COMPOUNDS, 98 5.1 General, 98 5.2 Derivatives of Main Group elements, 98 5.3 Organometallic derivatives of transition .
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meth-eth-prop-but-pent-6 8 7 9 10 hex-hept-oct-non-dec-5 3.2 Naming Organic Compounds Organic H 3C CH 2 CH 2 CH 3 H 2C CH2 H 2C CH CH 2 3.3 Naming Organic Compounds Organic H 3C CH CH CH2 H3C CH CH3 CH3 CH 3 CH 3 CH 3 3.4 Naming Organic Compounds Organic Name all
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