* Advanced Organic Chemistry Revision on the NAMING & STRUCTURE of AROMATIC COMPOUNDS at Doc Brown's
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Doc Brown's Chemistry REVISING ORGANIC CHEMISTRY Notes on the Molecular Structure and Nomenclature-naming of Aromatic Compounds - Arenes and substituted products Examples of displayed formula of aromatic compounds, graphic formula, molecular formula, skeletal formula, structural formula and please note that some 'old' names are quoted in () though their use should be avoided if possible, however, many are still used - just put one into Google! Most names are based on the generic hexagonal 'benzene' ring with modifications to this based on the highest functional group attached to the ring (i.e. a ring substituent replacing a hydrogen) Revision notes for GCE Advanced Subsidiary Level AS Advanced Level A2 IB Revise AQA GCE Chemistry OCR GCE Chemistry Edexcel GCE Chemistry Salters Chemistry CIE Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and Honours/honors level courses) KEYWORDS: fast track to nomenclature examples of ... Hydrocarbons (Arenes) ... Halo-Aromatics ... Phenols ... Aldehydes and Ketones ... Carboxylic Acids and Derivatives ... Amines (prim/sec/tert) ... Amides ... Diazonium Salts and azo dyes ... Nitro-Aromatics ... Sulphonic Acids Type in name QUIZ * Functional Group Tests * Summary of FUNCTIONAL GROUPS * EMAIL query?comment See ALKANES page for comparison with aliphatic and alicyclic compounds The shapes and bond angles of simple molecules - section on bond angles in organic molecules
Aromatic Hydrocarbons (Arenes) benzene C6H6,
methylbenzene (toluene) C7H8, C6H5CH3
ethylbenzene
phenylethene
('styrene'), the C6H5- aromatic ring grouping is called a phenyl group when quoted as a substituent prefix. So phenylethene is named as a derivative of ethene.
1,2-dimethylbenzene (once called xylenes, ortho, meta and para-xylene)
1-ethyl-2-methylbenzene 1-ethyl-3-methylbenzene
1,2-diethylbenzene
1-methyl-2-propylbenzene 1-methyl-3-propylbenzene 1-methyl-4-propylbenzene
1-ethyl-4-propylbenzene 4-ethyl-1,2-dimethylbenzene:
Halo-arenes - aryl 'halides' or aryl halide, aromatic halogen compounds, the halogen is directly attached to the benzene ring.
chlorobenzene
chloro-2-methylbenzene, chloro-3-methylbenzene and chloro-4-methylbenzene,or 1-chloro-2-methylbenzene, 1-chloro-3-methylbenzene and 1-chloro-4-methylbenzene (old names 0-chlorotoluene, m-chlorotoluene and p-chlorotoluene). These are true aryl halides with the halogen attached directly to the benzene ring and they are isomeric with (chloromethyl)benzene above.
2,3-dichloromethylbenzene
Phenols - aryl hydroxy compounds If the OH group (hydroxy) is directly attached to a benzene ring, the molecule is classified as a 'phenol'. If not, the molecule is classified as an aliphatic alcohol. This difference is illustrated below with molecules containing a benzene ring (Phenols ROH, R=aryl only)
Phenols form salts with strong bases e.g. the alkali sodium hydroxide gives ....
which is oxidised to
If the OH is not attached to a benzene ring you get an aliphatic alcohol which is isomeric with a phenols or an ether.
which is isomeric with
methylphenols and the ether,
Aromatic aldehydes and ketones True aromatic aldehydes, R-CHO, have the aldehyde group -CHO directly attached to the ring e.g.
Ketones, R2C=O, are often 'mixed' aliphatic-aromatic in the sense that one R group is alkyl and the other is aryl e.g. 1-phenylethanone (acetophenone, methyl phenyl ketone) Diphenylmethanone (diphenyl
ketone),
Aromatic acids and their derivatives Note: quite a few of the 'old' names are still used and accepted
(primary, 2 H's and only one R group attached to the N of the amine group, R-NH2 where R = alkyl or aryl) The amino (prefix) or amine (suffix) group is directly attached to the aromatic benzene ring e.g. the simplest is C6H5NH2,
phenylamine
2-
or 3-
or 4-chlorophenylamine
1,3-diaminobenzene,
2-methylphenylamine, methyl-2-phenylamine, 1-amino-2-methylbenzene
This is isomeric with
benzylamine
Secondary AROMATIC amines (secondary, one H and two R groups attached to the N of the amine group, R2NH where R = alkyl or aryl) N-methylphenylamine
and diphenylamine
(tertiary, no H and three R groups attached to the N of the amine group, R3N where R = alkyl or aryl) N,N-dimethylphenylamine
and triphenylamine
(primary, no alkyl/aryl R group and 2H's on the N of amide group) The simplest primary aromatic acid amide is
benzamide
or benzenecarboxamide,
(secondary, 1 alkyl/aryl R group and 1H on the N of amide group) N-phenylethanamide, N-methylbenzamide,
Are secondary amides formed in a condensation reaction between a carboxylic acid and an amine. Water is eliminated between the two 'monomers' to give the secondary, polyamide (polymer) linkage ... -COOH
+ H2N-
==> -CO-NH- + H2O
KEVLAR is an aromatic polyamide formed from benzene-1,4-dicarboxylic acid and 1,4-diaminobenzene
Tertiary amides would have no H and 2 aryl/alkyl groups on N of amide group. N,N-dimethylbenzamide,
DIAZONIUM SALTS and AZO DYES: Diazonium salts are formed when primary aromatic amines reaction with nitrous acid e.g. C6H5NH2(aq) + HNO2(aq) + H+(aq) ==> C6H5N2+(aq) + 2H2O(l) The diazonium cation has a nitrogen-nitrogen triple bond system directly attached to the benzene ring e.g. (1) (2) (3)
In alkaline solution these diazonium salts couple with phenols and aromatic amines to form azo dyes. These dyes have benzene rings linked with an azo -N=N- bond system e.g. reacting (1) with phenol gives reacting (1) with phenylamine gives reacting (2) with phenol gives reacting (2) with phenylamine gives
These have the nitro -NO2 group directly attached to the ring. On reduction they form primary aromatic amines. nitrobenzene,
1-chloro-2-nitrobenzene
methyl-2-nitrobenzene, and the two other positional structural isomers
methyl-3-nitrobenzene,
and
methyl-4-nitrobenzene,
3-nitrobenzoic acid,
Sulphonic Acids (sulfonic acids) These molecules have a strongly mono-basic acidic group -SO2OH directly attached to the benzene ring e.g.
benzenesulphonic acid,
2-, 3- or
4-methylbenzenesulfonic acid,
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| (korean) 브라운 박사는 화학 화학 개정 화합물의 아로마틱 노트에 마 그 분자 구조 명명 및 은 및 대체 제품 공식 골격 수식, 분자 예의 표시 수식의 방향족 화합물, 그래픽 분유, 구조적 수식과주십시오 일부 '늙은'의 이름이 사용 아직도 따온에서 피해야 ()되어야 사용하는 그들의 생각하는 경우 가능, 그러나 있으며, 많은 - 그냥 에 총알을 박아! 대부분의 이름)은 수소에서 가장 높은 그룹 기능이 첨부된 기반으로하는 수정을 기반으로 일반 반지 '육각형'벤젠 대체 반지 (예은 반지 * (portuguese) Doc Brown REVISÃO Química Química Orgânica Notas sobre a t ele Molecular Estrutura e Nomenclatura de nomeação de compostos aromáticos - Arenes e substituídos os produtos Exemplos de fórmulas indicadas de compostos aromáticos, fórmula gráfica, a fórmula molecular, fórmula esquelético, fórmula estrutural e, por favor, note que alguns "velhos" nomes são citados em (), embora seu uso deve ser evitado, se possível, no entanto, muitos ainda são utilizados - apenas colocar um no Google! A maioria dos nomes são baseados no hexagonal do benzeno "genérico anel com modificações para isso com base na maior grupo funcional ligado ao anel (isto é, um substituinte substituir um anel de hidrogênio) Revisão de notas Subsidiária Nível Avançado Rever Química CIE revisão cursos para estudantes pré-universitários (igual E.U. grau 11 e grau 12 e Títulos / nível de cursos de honras) PALAVRAS-CHAVE: acelerado a nomenclatura exemplos de ... Hidrocarbonetos (Arenes) ... Halo aromáticos ... Fenóis ... aldeídos e cetonas ... Ácidos Carboxílicos e Derivados ... Aminas (prim / seg / terc). .. Amidas ... diazônio sais e corantes azo ... Nitro-Aromatics ... sulfónico Ácidos * (spanish) REVISION Química Orgánica Notas sobre el l Estructura Molecular y nomenclatura de denominación de compuestos aromáticos - Arenes y sustituido productos just put one into Google! Ejemplos de la fórmula muestra de compuestos aromáticos, fórmula desarrollada, fórmula molecular, la fórmula del esqueleto, fórmula estructural y tenga en cuenta que algunos de los antiguos "los nombres son citados en () aunque su uso debe evitarse en lo posible, sin embargo, muchos todavía se usan - sólo poner uno en Google! La mayoría de los nombres se basan en la hexagonal de benceno »« genérica el anillo con las modificaciones a esta basado en el más alto grupo funcional unido al anillo (es decir, un sustituyente del anillo sustituir un hidrógeno) * (french) Doc Brown Chimie RÉVISION CHIMIE ORGANIQUE Notes sur les t-il la structure moléculaire et de la nomenclature de nommage des composés aromatiques - Arènes et remplacé par des produits. Exemples de formule affichée de composés aromatiques, d'une formule graphique, formule moléculaire, la formule du squelette, la formule développée et s'il vous plaît noter que certains «anciens» les noms sont indiqués en () si leur utilisation devrait être évitée si possible, cependant, beaucoup sont encore utilisés - tout mettre un dans Google! La plupart des noms sont basés sur hexagonale du benzène »l'anneau du générique, avec les adaptations de la présente base sur la plus haute du groupe fonctionnel lié à un cycle (par exemple un anneau de remplacement d'un substituant l'hydrogène) MOTS-CLÉS: voie rapide à la nomenclature des exemples de ... Hydrocarbures (Arènes) ... Halo-aromatiques ... Phénols ... aldéhydes et des cétones ... Acides carboxyliques et dérivés ... Amines (prim / sec / tert). .. Amides ... sels de diazonium et les colorants azoïques ... Nitro-aromatiques ... Acides sulfoniques * |