* Revision Notes on the NAMING & STRUCTURE of ORGANIC NITROGEN COMPOUNDS at Doc Brown's

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 Doc Brown's Chemistry

The Classification, Molecular Structure and Nomenclature-naming of Organic compounds containing Nitrogen in the molecules

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)

Examples of displayed formula of molecules, graphic formula, molecular formula, skeletal formula, structural formula of these homologous series. Some 'old' names are quoted in (), but their use should be avoided if possible.

Fast track to nomenclature examples of .. Primary amines .. Secondary amines .. Tertiary Amines .. Quaternary ammonium salts .. Amino acids and zwitterions .. Primary acid amides .. Secondary acid amides .. Polyamides (nylons) & polypeptides .. Tertiary acid amides ... Diazonium salts and azo dyes .. Nitro-aromatics .. Nitriles

summary of functional groups and homologous series * organic chemical identity tests

 

m/c quiz on structure/names of N compounds * type in name quiz on N compounds

Intermolecular forces & boiling points of primary aliphatic amines & amides compared to other organic molecules

The shapes and bond angles of simple molecules - section on bond angles in organic molecules


PRIMARY AMINES

These have two hydrogen atoms and one alkyl or aryl group attached to the nitrogen to form the amine or amino group -NH2.

ALIPHATIC: methylamine (aminomethane), (c) doc b, (c) doc b, (c) doc b, (c) doc b

ethylamine (aminoethane), (c) doc b, (c) doc b, (c) doc b, (c) doc b

propylamine, (1-aminopropane), (c) doc b,(c) doc b, (c) doc b

2-aminopropane, (c) doc b, (c) doc b

butylamine, (1-aminobutane), (c) doc b, (c) doc b

2-aminobutane, (c) doc b, (c) doc b 

1-aminopentane, (pentylamine) (c) doc b, (c) doc b

2-aminopentane, (c) doc b, (c) doc b

3-aminopentane, (c) doc b, (c) doc b

1-aminohexane, (hexylamine), (c) doc b, (c) doc b

2-aminohexane, (c) doc b, (c) doc b

3-aminohexane, (c) doc b, (c) doc b

examples of primary diamines:

1,2-diaminoethane, (c) doc b, (c) doc b, (c) doc b

1,3-diaminopropane, (c) doc b, (c) doc b

1,4-diaminobutane, (c) doc b, (c) doc b

1,5-diaminopentane, (c) doc b, (c) doc b

2,3-diaminopentane, (c) doc b, (c) doc b

2,4-diaminopentane, (c) doc b, (c) doc b

1,4-diaminohexane, (c) doc b, (c) doc b

1,6-diaminohexane, (c) doc b, (c) doc b

examples of primary cyclo-amines: e.g.

cyclopentylamine, aminocyclopentane, (c) doc b ,(c) doc b

aminocyclohexane, cyclohexylamine, (c) doc b, (c) doc b

TOP links sub-indexbenzylamine, (c) doc b aliphatic, NOT aromatic, compare with one of its isomers 2-methylphenylamine below.

examples of primary AROMATIC amines where the amino or amine group is directly attached to the aromatic benzene ring ....

e.g. the simplest is C6H5NH2 phenylamine (aniline) (c) doc b

1,3-diaminobenzene,  (c) doc b 3-aminobenzoic acid,  (c) doc b

2-methylphenylamine, methyl-2-phenylamine, 1-amino-2-methylbenzene (c) doc b ,

this is isomeric with phenylmethylamine or benzylamine, which is a primary aliphatic amine because the amine group is NOT directly attached to the benzene ring.

(note: that many 'amino acids' are 'primary' amines - see below)

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SECONDARY AMINES

These have one hydrogen atom and two alkyl or aryl groups attached to the nitrogen

ALIPHATIC: dimethylamine, (c) doc b,(c) doc b, (c) doc b

ethylmethylamine, (c) doc b, (c) doc b

diethylamine, (c) doc b, (c) doc b

methylpropylamine, (c) doc b, (c) doc b

ethylpropylamine, (c) doc b, (c) doc b

dipropylamine, (c) doc b(c) doc b

examples of cyclo-secondary amines: e.g.

piperidine, (c) doc b, (c) doc b

N-methylcyclopentylamine, (c) doc b, (c) doc b

examples of secondary AROMATIC amines: e.g.

N-methylphenylamine(c) doc b, N-ethylphenylamine(c) doc b

and  diphenylamine(c) doc b

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TERTIARY AMINES

These have no hydrogen atom and three alkyl or aryl groups attached to the nitrogen

ALIPHATIC: trimethylamine, (c) doc b ,(c) doc b

ethyldimethylamine, (c) doc b, (c) doc b

diethylmethylamine, (c) doc b ,(c) doc b

triethylamine, (c) doc b, (c) doc b

two examples of cyclo-tertiary amines:

N-methylpyrrolidine, (c) doc b ,(c) doc b

and N-methylpiperidine, (c) doc b, (c) doc b

examples of tertiary AROMATIC amines: e.g.

N,N-dimethylphenylamine (c) doc b, N,N-diethylphenylamine (c) doc b

and triphenylamine (c) doc b

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QUATERNARY AMMONIUM SALTS

If all for hydrogens of an ammonium ion are replaced with alkyl or aryl groups then an ionic quaternary salt is formed.

e.g. the simplest is tetramethylammonium chloride, (CH3)4N+ Cl-

tetrapropylammonium chloride, (CH3CH2CH2)4N+ Cl-

and the R groups can be mixed e.g. [(CH3CH2CH2)3NC6H5]+ Cl-

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AMINO ACIDS and ZWITTERIONS

The primary suffix name for an aliphatic carboxylic acid is based on the "longest carbon chain name *" for the -COOH bond system e.g.  ethanoic acid, propanoic  acid etc. The amino group -NH2, with its C-atom position number, is added as a prefix. [* without the end 'e'] Many amino-acids in aqueous solution, or in the crystalline state, exist as 'zwitterions' where the proton migrates from the acidic -COOH group to the basic -NH2  group to form the ionic groups -NH3+ and -COO- BUT within the same 'molecule'.

aminoethanoic acid, (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b

2-aminopropanoic acid , (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b

 3-aminopropanoic acid ,(c) doc b ,(c) doc b , (c) doc b, (c) doc b

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PRIMARY ACID AMIDES

The primary suffix name for an aliphatic acid amide is based on the "longest carbon chain name *" + "amide" for the CONH2 bond system at the end of the carbon chain e.g. methanamide, ethanamide etc. [* without the end 'e'] There are two hydrogens on the N of the amide group.

methanamide,(c) doc b,(c) doc b,(c) doc b

ethanamide , (c) doc b,(c) doc b ,(c) doc b , (c) doc b

propanamide , (c) doc b, (c) doc b, (c) doc b

butanamide , (c) doc b, (c) doc b, (c) doc b

pentanamide , (c) doc b, (c) doc b, (c) doc b

benzamide,(c) doc b, (c) doc b,(c) doc b, (the simplest primary aromatic acid amide)

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SECONDARY ACID AMIDES

These have one hydrogen and one alkyl or aryl group on the N of the amide group.

N-methylethanamide, (c) doc b; N-phenylethanamide, (c) doc b

N-methylbenzamide, (c) doc b; N-phenylbenzamide, (c) doc b 

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POLYAMIDES and POLYPEPTIDES 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) or polypeptide (if in proteins) linkage ...

-COOH + H2N- ==> -CO-NH- + H2O (c) doc b is the basic condensation 'polymeric' process.

(1) KEVLAR is formed from benzene-1,4-dicarboxylic acid and 1,4-diaminobenzene

(c) doc b

(2) in proteins, amino acids link together  in a condensation reaction to form peptides e.g. Alanine (Ala, 2-aminopropanoic acid) links with Glycine (Gly, aminoethanoic acid) to form the dipeptide AlaGly (in 'biochemical' shorthand!)  (c) doc b displayed graphical formula

or the skeletal formula  (c) doc b

Proteins are built up in this way to form long chains of amino-acid residues after the elimination of water ...

i.e. nH2NCH(R)COOH ==> -(-NH-CH(R)-CO-)n- + n H2O

where R is the variable 'sidechain' from the original amino acid

(3) NYLONS are formed by condensing together a dicarboxylic acid and a diamine (nylon-x,y) OR polymerising an amino carboxylic acid (nylon-y). [x = length carbon atoms in amine, y = length of carbon atoms in carboxylic acid]

nylon-5 (c) doc b, (c) doc b

nylon-6 (c) doc b, (c) doc b

nylon-7 (c) doc b, (c) doc b

nylon-8 (c) doc b, (c) doc b

nylon-9 (c) doc b, (c) doc b

nylon 10 (c) doc b, (c) doc b

nylon-3,7 (c) doc b, (c) doc b

nylon-4,6 (c) doc b, (c) doc b

nylon-4,8 (c) doc b, (c) doc b

nylon-5,7 (c) doc b, (c) doc b

nylon-6,6 (c) doc b, (c) doc b

nylon-7,7 (c) doc b, (c) doc b

nylon-7,9 (c) doc b, (c) doc b

nylon-7,11 (c) doc b, (c) doc b

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TERTIARY ACID AMIDES

These have two alkyl or aryl groups attached to the N of the amide group.

N,N-dimethylethanamide, (c) doc b, (c) doc b

N,N-dimethylbenzamide, (c) doc b

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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) (c) doc bfrom phenylamine+

(2) (c) doc bfrom 4-methylphenylamine

(3) (c) doc bfrom 2-aminobenzoic acid. In alkaline solution these diazonium salts couple with phenols and aromatic amines to form azo dyes which have benzene rings linked with an azo -N=N- bond system e.g.

reacting (1) with phenol gives (c) doc b

reacting (1) with phenylamine gives (c) doc b

reacting (2) with phenol gives(c) doc b 

reacting (2) with phenylamine gives (c) doc b

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NITRO-AROMATICS

These have the nitro -NO2 group directly attached to the ring. On reduction they form primary aromatic amines.

nitrobenzene, (c) doc b; 1,3-dinitrobenzene, (c) doc b

methyl-2-nitrobenzene, (c) doc b; 3-nitrobenzoic acid, (c) doc b

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NITRILES

The nitrile functional group consists of a carbon to nitrogen triple bond. The name is based on the longest carbon chain, including the C of the nitrile group.

methanenitrile (methanonitrile, hydrogen cyanide), (c) doc b, (c) doc b, (c) doc b

ethanenitrile (ethanonitrile, acetonitrile), (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b

propanenitrile (propanonitrile, ethyl cyanide), (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b, (c) doc b

 

(indonesia) Doc Brown Kimia Klasifikasi, M Struktur olecular dan Nomenklatur-penamaan senyawa organik yang mengandung Nitrogen dalam molekul Contoh formula ditampilkan molekul, rumus grafis, rumus molekul, rumus kerangka, struktur formula dari seri homolog. Some 'old' names are quoted in (), but their use should be avoided if possible. Beberapa "lama" nama yang dikutip dalam (), tetapi penggunaannya harus dihindari jika mungkin. Nitriles Cepat melacak tata-nama, contoh .. amina Primer .. amina sekunder .. Amina tersier .. Kuarter garam amonium .. asam amino dan zwitterions .. asam Primer Amida .. asam Sekunder Amida .. poliamida (nilon) & polipeptida .. Tersier Amida asam ... Diazonium garam dan pewarna azo .. -Nitro aromatik .. Nitril * (bulgarian) Док Браун химия Класификацията, M olecular Структура и номенклатура-именуване на органични съединения, съдържащи азот в молекулата Примери на показаната формула на молекулата, графични формула, молекулната формула, скелетни формула, структурна формула на тези хомоложна серия. Някои "стари" имена са цитирани в (), но тяхната употреба трябва да се избягва, ако е възможно. Бърза писта за номенклатура примери за .. Първичен амини .. Средно амини .. третични амини .. кватернерни амониеви соли .. аминокиселини и zwitterions .. Първичен киселина амиди .. Средно киселина амиди .. Полиамиди (найлонови чорапи) & полипептиди .. Терциер киселина амиди ... Diazonium соли и азо багрила .. нитро-ароматните нитрили * (japanese) ドックは、ブラウンの化学 分類は、構造と命名法は、分子の命名の窒素を含む有機化合物 式骨格表示式の例の分子、グラフィック式、分子式、同族これらの構造式の。 Some 'old' names are quoted in (), but their use should be avoided if possible. 一部の名前の古い'はしかし、いる引 用符で()の使用は可能な場合は避けるべきです。 高速トラックが...の例を命名する プライマリアミン .. 二級アミン .. 三級アミン .. 第四アンモニウム塩 .. アミノ酸と双性イオン .. プライマリ酸アミド .. 二酸アミド .. ポリアミド(ナイロン)&ポリペプチド .. 第三紀酸アミド ... ジアゾニウム塩とアゾ染料 .. ニトロ芳香族化合物 .. ニトリル * (spanish) Doc Brown de Química La Clasificación, M olecular Estructura y nomenclatura de denominación de compuestos orgánicos que contienen nitrógeno en las moléculas La revisión nota de la CME Nivel Avanzado Subsidiario Avanzado Nivel del Revisar CME Química Química revisión cursos para estudiantes de pre-universitario (equivalente al grado 11 y EE.UU. 12 º grado y honores / cursos de honores). Ejemplos de la fórmula muestra de moléculas, fórmula desarrollada, fórmula molecular, la fórmula del esqueleto, la fórmula estructural de estas series homólogas. Algunos son viejos "nombres se citan en (), pero su uso debe evitarse en lo posible. Nitriles vía rápida a la nomenclatura .. ejemplos de aminas primarias .. aminas secundarias .. aminas terciarias .. sales de amonio cuaternario .. Aminoácidos y zwitteriones .. ácido Primaria amidas .. ácido Secundaria amidas .. Poliamidas (nylon) y polipéptidos .. Terciario amidas del ácido ... diazonio sales y colorantes azoicos .. aromáticos Nitro .. Nitrilos *

TOP links sub-indexCopyright © Dr W P Brown 2000-2010 All rights reserved on the revision notes pages, quizzes, worksheets, x-words etc.

(indonesia) Doc Brown Kimia Klasifikasi, M Struktur olecular dan Nomenklatur-penamaan senyawa organik yang mengandung Nitrogen dalam molekul Contoh formula ditampilkan molekul, rumus grafis, rumus molekul, rumus kerangka, struktur formula dari seri homolog. Some 'old' names are quoted in (), but their use should be avoided if possible. Beberapa "lama" nama yang dikutip dalam (), tetapi penggunaannya harus dihindari jika mungkin. Nitriles Cepat melacak tata-nama, contoh .. amina Primer .. amina sekunder .. Amina tersier .. Kuarter garam amonium .. asam amino dan zwitterions .. asam Primer Amida .. asam Sekunder Amida .. poliamida (nilon) & polipeptida .. Tersier Amida asam ... Diazonium garam dan pewarna azo .. -Nitro aromatik .. Nitril * (bulgarian) Док Браун химия Класификацията, M olecular Структура и номенклатура-именуване на органични съединения, съдържащи азот в молекулата Примери на показаната формула на молекулата, графични формула, молекулната формула, скелетни формула, структурна формула на тези хомоложна серия. Някои "стари" имена са цитирани в (), но тяхната употреба трябва да се избягва, ако е възможно. Бърза писта за номенклатура примери за .. Първичен амини .. Средно амини .. третични амини .. кватернерни амониеви соли .. аминокиселини и zwitterions .. Първичен киселина амиди .. Средно киселина амиди .. Полиамиди (найлонови чорапи) & полипептиди .. Терциер киселина амиди ... Diazonium соли и азо багрила .. нитро-ароматните нитрили * (japanese) ドックは、ブラウンの化学 分類は、構造と命名法は、分子の命名の窒素を含む有機化合物 式骨格表示式の例の分子、グラフィック式、分子式、同族これらの構造式の。 Some 'old' names are quoted in (), but their use should be avoided if possible. 一部の名前の古い'はしかし、いる引 用符で()の使用は可能な場合は避けるべきです。 高速トラックが...の例を命名する プライマリアミン .. 二級アミン .. 三級アミン .. 第四アンモニウム塩 .. アミノ酸と双性イオン .. プライマリ酸アミド .. 二酸アミド .. ポリアミド(ナイロン)&ポリペプチド .. 第三紀酸アミド ... ジアゾニウム塩とアゾ染料 .. ニトロ芳香族化合物 .. ニトリル * (spanish) Doc Brown de Química La Clasificación, M olecular Estructura y nomenclatura de denominación de compuestos orgánicos que contienen nitrógeno en las moléculas La revisión nota de la CME Nivel Avanzado Subsidiario Avanzado Nivel del Revisar CME Química Química revisión cursos para estudiantes de pre-universitario (equivalente al grado 11 y EE.UU. 12 º grado y honores / cursos de honores). Ejemplos de la fórmula muestra de moléculas, fórmula desarrollada, fórmula molecular, la fórmula del esqueleto, la fórmula estructural de estas series homólogas. Algunos son viejos "nombres se citan en (), pero su uso debe evitarse en lo posible. Nitriles vía rápida a la nomenclatura .. ejemplos de aminas primarias .. aminas secundarias .. aminas terciarias .. sales de amonio cuaternario .. Aminoácidos y zwitteriones .. ácido Primaria amidas .. ácido Secundaria amidas .. Poliamidas (nylon) y polipéptidos .. Terciario amidas del ácido ... diazonio sales y colorantes azoicos .. aromáticos Nitro .. Nitrilos *
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