Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK GCE IB advanced level organic chemistry students US K12 grade 11 grade 12 organic chemistry nomenclature of primary secondary tertiary amines tertiary quaternary ammonium amides amino acids zwitterions azo dyes

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 Nomenclature of organic nitrogen compounds examples of how to name 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, acid nitriles via displayed formula of molecules, graphic formula, molecular formula, skeletal formula, structural formula of various homologous series. naming empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism. Some 'old' names are quoted in (), but their use should be avoided if possible.

Fast track to nomenclature examples of organo-nitrogen compounds .. Introduction to classifying amines .. 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 .. and

Summary of how various types of organic nitrogen compounds are classified as primary, secondary or tertiary

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), CH₅N (molecular formula),  also methanamine

structural formulae , , displayed formula , skeletal formula

ethylamine (aminoethane, ethanamine), molecular formula C₂H₇N, structural formulae , , full displayed/graphic structural formula, skeletal formula  

propylamine, 1-aminopropane, C₃H₉N, ,,   also propanamine, propan-1-amine

2-aminopropane, ,  also propan-2-amine

butylamine, (1-aminobutane),  C₄H₁₁N,, also butan-1-amine

2-aminobutane, ,   also butan-2-amine

1-aminopentane (pentylamine), C₅H₁₃N, , also pentan-1-amine

2-aminopentane, , also pentan-2-amine

3-aminopentane, , also pentan-3-amine

1-aminohexane (hexylamine), C₆H₁₅N, , also hexan-1-amine

2-aminohexane, , also hexan-2-amine

3-aminohexane, , also hexan-3-amine

examples of primary diamines:

1,2-diaminoethane, C₂H₈N₂, , ,

1,3-diaminopropane, C₃H₁₀N₂, ,

1,4-diaminobutane, C₄H₁₂N₂, , known as putrescine

1,5-diaminopentane, C₅H₁₄N₂, , known as cadavarine

putrescine and cadavarine are formed when dead fish and other animal bodies rot, hence their names and rotten smell!

2,3-diaminopentane, ,

2,4-diaminopentane, ,

1,4-diaminohexane, C₆H₁₆N₂, ,

1,6-diaminohexane, ,

examples of primary cyclo-amines: e.g.

cyclopentylamine, aminocyclopentane, C₅H₁₁N₂, ,

aminocyclohexane, cyclohexylamine, C₆H₁₃N₂, ,

benzylamine, C₇H₉N, 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 , C₆H₇N_, C₆H₅NH₂,  phenylamine (aniline)

1,3-diaminobenzene, C₆H₈N₂,  , 

3-aminobenzoic acid, 

2-methylphenylamine, methyl-2-phenylamine, 1-amino-2-methylbenzene  ,

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: N-methylmethylamine, ,, (dimethylamine)

Here the other alkyl group is treated as an substituent of the N atom of the amine.

If the alkyl group rankings are different, the short lower ranking alkyl group is treated as the substituent.

I have included some of the older common names still in use.

N-methylethylamine, , (ethylmethylamine) also N-methylethanamine

N-ethylethylamine, , (diethylamine) also N-ethylethanamine

N-methylpropylamine, , (methylpropylamine), N-methylpropanamine, N-methylpropan-1-amine

N-ethylpropylamine, , (ethylpropylamine) also N-ethylpropanamine, N-ethylpropan-1-amine

N-propylpropylamine, ,  (dipropylamine) N-propylpropylamine, N-propylpropan-1-amine

examples of cyclo-secondary amines: e.g.

piperidine, C₅H₁₁N, ,

N-methylcyclopentylamine, C₆H₁₃N, ,

examples of secondary AROMATIC amines: e.g.

N-methylphenylamine, C₇H₉N, , N-ethylphenylamine, C₈H₁₁N,

and  N-phenylphenylamine, C₁₂H₁₁N,  (diphenylamine)

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TERTIARY AMINES

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

ALIPHATIC: N,N-dimethylmethylamine, , (trimethylamine)

Here the other alkyl groups are treated as substituents of the N atom of the amine.

If the alkyl group rankings are different, the short lower ranking alkyl groups are treated as the substituent.

I have included some of the older common names still in use.

N,N-dimethylethylamine, , (ethyldimethylamine)

N-ethyl-N-methylethylamine, , (diethylmethylamine)

N,N-diethylethylamine, , (triethylamine)

two examples of cyclo-tertiary amines:

N-methylpyrrolidine, ,

and N-methylpiperidine, ,

examples of tertiary AROMATIC amines: e.g.

N,N-dimethylphenylamine   and  N,N-diethylphenylamine

and N,N-diphenlyphenylamine (triphenylamine)

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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^-

tetraethylammonium chloride, (CH₃CH₂)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 carboxylic -COOH group to the basic -NH₂ amino group to form the ionic groups -NH₃⁺ and -COO^– BUT within the same 'molecule'.

H₂N-CHR-COOH    ⁺H₃N-CHR-COO^–  (R = H, alkyl, aryl or a variety of other groups)

aminoethanoic acid, C₂H₅NO₂, , , , ,

2-aminopropanoic acid, C₃H₇NO₂, , , , ,

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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.

benzamide, C₇H₇NO,, ,, (the simplest primary aromatic acid amide)

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

N-methylethanamide, ; N-phenylethanamide,

N-methylbenzamide, ; N-phenylbenzamide,  

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POLYAMIDES and POLYPEPTIDES

These 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 is the basic condensation 'polymeric' process.

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

(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!)  displayed graphical formula

or the skeletal formula  

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 'side chain' 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 ,

nylon-6 ,

nylon-7 ,

nylon-8 ,

nylon-9 ,

nylon 10 ,

nylon-3,7 ,

nylon-4,6 ,

nylon-4,8 ,

nylon-5,7 ,

nylon-6,6 ,

nylon-7,7 ,

nylon-7,9 ,

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

N,N-dimethylethanamide, ,

N,N-dimethylbenzamide,

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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) + HNO_2(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) from phenylamine+

(2) from 4-methylphenylamine

(3) from 2-aminobenzoic acid. In alkaline solution these diazonium salts couple with phenols, and in neutral solution with 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:

reacting (1) with phenylamine gives:

reacting (2) with phenol gives:

reacting (2) with phenylamine gives:

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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, C₆H₅NO₂, ; 1,3-dinitrobenzene, C₆H₄N₂O₄,

methyl-2-nitrobenzene, C₇H₇NO₂, ; 3-nitrobenzoic acid,

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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), , ,

ethanenitrile (ethanonitrile, acetonitrile), C₂H₃N, , , , , ,

propanenitrile (propanonitrile, ethyl cyanide), C₃H₅N, , , , , ,

2-hydroxypropanenitrile, CH₃CH(OH)CN,

2-hydroxy-2-methylpropanenitrile

2-hydroxy-2-methylbutanenitrile,

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A summary of the way selected types of organic nitrogen compounds are classified

Functional group of the homologous series	PRIMARY	SECONDARY	TERTIARY	Comments
AMINES				There are prim/sec/tert aliphatic (alkyl) or aromatic (aryl) amines. See also Note 3. below the table.
aliphatic amine examples	ethylamine	ethylmethylamine	triethylamine	aliphatic amine examples
aromatic amine examples	phenylamine	diphenylamine	triphenylamine	aromatic amine examples
acyl or acid AMIDES				The amide group comprises an amine group attached to the C of a C=O carbonyl group, which gives it its own unique chemistry i.e. its neither an amine or an aldehyde or ketone!
examples of amides	ethanamide	N-methylbenzamide	N,N-dimethylethanamide	examples of amides both aliphatic and aromatic

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WHAT NEXT?

Fast track to nomenclature examples of organo-nitrogen compounds .. 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

formula keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism prim Primary amines .. sec Secondary amines .. tert 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 .. acid Nitriles CH5N CH3NH2 C2H7N C2H5NH2 CH3CH2NH2 C3H9N C3H7NH2 CH3CH2CH2NH2 C4H11N C4H9NH2 CH3CH2CH2CH2NH2 C5H13N C5H11NH2 CH3CH2CH2CH2CH2NH2 C6H13N C6H13NH2 C2H8N2 H2NCH2CH2NH2 NH2CH2CH2NH2 C3H10N2 H2NCH2CH2CH2NH2 NH2CH2CH2CH2NH2 C4H12N2 H2NCH2CH2CH2CH2NH2 NH2CH2CH2CH2CH2NH2 C5H14N2 H2NCH2CH2CH2CH2CH2NH2 NH2CH2CH2CH2CH2CH2NH2 C6H16N2 H2NCH2CH2CH2CH2CH2CH2NH2 NH2CH2CH2CH2CH2CH2CH2NH2 C5H11N C6H13N C7H9N C6H5CH2NH2 C6H7N C6H5NH2 C6H8N2 C5H11N C6H13N C6H5NHCH3 C6H5NHCH2CH3 C7H9N C8H11N C12H11N C6H5NHC6H5 C18H15N C2H5O2N C2H5NO2 H2NCH2COOH NH2CH2COOH C3H7O2N C3H7NO2 H2NCH2CH2COOH NH2CH2CH2COOH CH3CH(NH2)COOH CH3NO HCONH2 C2H5NO CH3CONH2 C3H7NO CH3CH2CONH2 C4H9NO CH3CH2CH2CONH2 C5H9NO CH3CH2CH2CH2CONH2 C7H7NO C6H5CONH2 C6H5NO2 C6H4N2O4 C7H7NO2 CH3C6H5NO2 HCN CHN C2H3N CH3CN C3H5N CH3CH2CN advanced level chemistry how to name organic nitrogen compounds for AQA AS chemistry, how to name organic nitrogen compounds for Edexcel A level AS chemistry, how to name organic nitrogen compounds for A level OCR AS chemistry A, how to name organic nitrogen compounds for OCR Salters AS chemistry B, how to name organic nitrogen compounds for AQA A level chemistry, how to name organic nitrogen compounds for A level Edexcel A level chemistry, how to name organic nitrogen compounds for OCR A level chemistry A, how to name organic nitrogen compounds for A level OCR Salters A level chemistry B how to name organic nitrogen compounds for US Honours grade 11 grade 12 how to name organic nitrogen compounds for pre-university chemistry courses pre-university A level revision notes for how to name organic nitrogen compounds  A level guide notes on how to name organic nitrogen compounds for schools colleges academies science course tutors images pictures diagrams for how to name organic nitrogen compounds A level chemistry revision notes on how to name organic nitrogen compounds for revising module topics notes to help on understanding of how to name organic nitrogen compounds university courses in science careers in science jobs in the industry laboratory assistant apprenticeships technical internships USA US grade 11 grade 11 AQA A level chemistry notes on how to name organic nitrogen compounds Edexcel A level chemistry notes on how to name organic nitrogen compounds for OCR A level chemistry notes WJEC A level chemistry notes on how to name organic nitrogen compounds CCEA/CEA A level chemistry notes on how to name organic nitrogen compounds for university entrance examinations with advanced level chemistry nomenclature of organic nitrogen compounds, how do you name primary amines? how do you name secondary amines? how do you name tertiary amines? the molecular structure of primary, secondary and tertiary amines, how to draw skeletal formula of amines, what is the molecular structure of quaternary ammonium salts? what is the molecular structure of amino acids?  how do you draw the skeletal structures of amino acids? how do you name amino acids? nomenclature of amino acids, what is the molecular structure of a primary acid amide? how do you name primary acid amides? what is the structure of a secondary acid amide? what is the nomenclature of secondary acid amides, how do you draw the skeletal structures of amides acids? structure of polyamides and polypeptides, molecular structure of nylons, how do you name nylon polymer molecules? what is the structure of a tertiary acid amide? what is the molecular structure of diazonium salts and azo dyes? how do you name nitro-aromatic compounds? what is the molecular structure of aromatic nitro compounds? what is the molecular structure of nitriles? how do you name nitriles? how do you draw the skeletal structures of nitriles? including general formula of amines molecules, empirical formula of amines molecules, structural formula of amines molecules, skeletal formula of amines molecules, displayed formula of amines molecules, shapes of amines molecules, isomers of amines molecules IUPAC rules for amines nomenclature. Students should be able to draw structural formula of amines, displayed and skeletal formulas for amines organic compounds apply IUPAC rules for  nomenclature to name amines acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of amines organic compounds from the amines IUPAC name from the homologous series of amines including general formula of amides molecules, empirical formula of amides molecules, structural formula of amides molecules, skeletal formula of amides molecules, displayed formula of amides molecules, shapes of amides molecules, isomers of amides molecules IUPAC rules for amides nomenclature. Students should be able to draw structural formula of amides, displayed and skeletal formulas for amides organic compounds apply IUPAC rules for  nomenclature to name amides acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of amides organic compounds from the amides IUPAC name from the homologous series of amides including general formula of amino acids molecules, empirical formula of amino acids molecules, structural formula of amino acids molecules, skeletal formula of amino acids molecules, displayed formula of amino acids molecules, shapes of amino acids molecules, isomers of amino acids molecules IUPAC rules for amino acids nomenclature. Students should be able to draw structural formula of amino acids, displayed and skeletal formulas for amino acids organic compounds apply IUPAC rules for  nomenclature to name amino acids acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of amino acids organic compounds from the amino acids IUPAC name from the homologous series of amino acids including general formula of organonitrogen molecules, empirical formula of organonitrogen molecules, structural formula of organonitrogen molecules, skeletal formula of organonitrogen molecules, displayed formula of organonitrogen molecules, shapes of organonitrogen molecules, isomers of organonitrogen molecules IUPAC rules for organonitrogen nomenclature. Students should be able to draw structural formula of organonitrogen, displayed and skeletal formulas for organonitrogen organic compounds apply IUPAC rules for  nomenclature to name organonitrogen acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of organonitrogen organic compounds from the organonitrogen IUPAC name from the homologous series of organonitrogen

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