Organicnomenclature

Organic Chemistry Nomenclature

1. Hydrocarbonso Alkanes o Alkenes o Alkyneso Unsaturated hydrocarbonso Cyclohydrocarbonso Aromatic compounds

2. Other functional groupso Alkyl Halideso Amineso Etherso Alcoholso Aldehides & ketoneso Carboxilic acido Salts o Esterso Amideso Nitriles

3. Isomery Patricio Gómez Lesarri

1. Introduction

Substances which consist of carbon & hydrogen (hydrocarbons)

Heteroatoms: O, N, S, P, Halogens, alkalines, etc.

Carbon tetravalence

C-C bond intensity and length (350 kJ/mol)

Chains and polymers

1.1. AlkanesSingle bond: saturated

hydrocarbons

Primary carbon: - CH3

Secondary carbon: -CH2-

Tertiary carbon: -CH-

Nomenclature: Stem + ane

General formula: CnH2n+2

1.1. Substituted alkanesMain chain: longest chain of atoms of carbon

Substituent: branch chain attached to the main chain It is named with suffix -yl

Nomenclature: branch + main chain

1.1. Branches & substituents

Branchs + main chain

Locants: numbers which precedes a substituent and show its position.

Hyphen between locant and name. Comma between two locants

Chain numbered in order to get lowest locants as possible

Substituents alphabetically ordered

Prefixes: di-, tri- tetra- for several branches

1.1. Branched alkanes

When some main chains of the same length are identified, we choose one which has greater number of branches

1.1. Branched alkanes

When there are several main chains of the same length and number of substituents, the main chain is one which has the lowest locants

1.1. Branched alkanes

1.2. AlkenesDouble bond

Nomenclature: Stem + ene

General formula: CnH2n

Locant just before the suffix –ene

Lowest locant as possible for double bonds

1.2. Branched alkenes

Prefixes di, tri, are used preceding suffix –ene

Main chain: one which has all the double bonds

Locant so as to give the place of branches and double bonds

2-methyl-3-sec-pentylpent-1,3-diene

2-ethyl-3,4-dimethylhex-1,3-diene

1.3. Alkynes

Nomenclature: Stem + yne

General formula: CnH2n-

2

Locant just before the suffix –yne

Lowest locant as possible for the triple bond

1.3. Branched alkynes

Prefixes di, tri, are used before suffix –yne

Main chain: one which has all the triple bonds

Use of locant so as to give the place of branches and triple bonds

CH3-CC-CCH

pent-1,3-diyne

1.3. Unsaturated hydrocarbons

Nomenclature: Stem + en + yne

Use of locants so as to give the position of unsaturations

Lowest locant as possible for all the unsaturations

When there are two choices lower locants are assigned to doubles bonds

1.4. CycloalkanesHydrocarbons with closed

chains: “rings”

Nomenclature: prefix Cyclo –

General formula: CnH2n

Locant for unsaturations or substituents

1.5. ArenesBenzen derivatives

Substituent: phenyl

DisubstitutedOrtho (1, 2)Meta (1, 3)Para (1, 4)

2. Other functional groupsFunctional group: group

of atmos or chemical bonds which give certain chemical properties to a molecule

Homogous serie: all the chemical substances which have the same functional group onjunto de compuestos con el mismo grupo funcional

Priority order

Name Functional group

Suffix(Main chain)

Prefix(substituent)

Carboxilic acid R-COOH - oic acid Carboxy -

Salts R-COO-M Metal - oate  

Esters R-COO-R Alkyl - oate  

Amides R-CONH2 - amide  

Nitriles R-CN - nitrile Cyano -

Aldehides R-CHO - al Oxo -

Ketones R-CO-R - one Oxo -

Alcohols R-OH - ol Hidroxi -

Amines R-NH2 -amine Amino -

Ethers R-O-R - ether Alkoxi -

Alkenes C=C - ene  

Alkynes CC - ine  

Halogen R-X - Halogen -

Alkyl R - ane - yl

2. Priority order

2.1.1 Alkyl halidesFunctional group:

halogen

General formula R-X

Nomenclatur:Alkyl halideSubstituent: halogen -

2.1.2 Ethers

Functional group: ether

General formula: R-O-R´

Nomenclature:Suffix ether:

AlkylalkyletherSubstituent: alkoxy

2.1.3 AminesFunctional group: amino

General formula: R-NH2

Nomenclature: Substituent amino -Sufix amina: Alquilamina

Types:Primary, Secondary,

Tertiary

2.1.4 AlcoholsFunctional group:

hydroxylGeneral formula: R-OHNomenclature:

Suffix –ol Substituent: hidroxi – Phenol

2.2.1 Aldehides

Functional group : carbonyl

Fórmula general: R-CHO

Nomenclature:Suffix: - alSubstituent: oxo –

2.2.2 Ketones

Functional group: carbonyl

General formula: R-CO-R´

Nomenclature: Suffix: - oneSuffix: alkylalkylketoneSubstituent : oxo -

2.2. Aldehides & ketones

2.3.1 Carboxilic acidsFunctional group: carboxyl

General formula: R-COOH

Nomenclature:Suffix: – oic acidSubstituent: carboxy -

2.3.2 Salts

Functional group: carboxyl

General formula: R-COO-M

Nomenclature: Suffix: Metal - oate

2.3.3 EstersFuncional group: ester

General formula: R-COO-R´

Nomenclature: Suffix: –alkyl - oate

2.3.4 Amides

Functional group: amide

General formula: R-CONH2

Nomenclature: Suffix: -amideSubstituent: carbamoil-

2.3.5 Nitriles

Functional group: nitrile

Fórmula general: R-CN

Nomenclature: Suffix: - nitrileSubstituent: cyano –HCN Cianhidric

acid/methanenitrile CN- cyanide