summary of homologous series
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Revising Advanced Level Organic Chemistry
Revision Notes Part 9 FUNCTIONAL GROUPS and HOMOLOGOUS SERIES
A summary guide to the Molecular Structure and Naming-Nomenclature of Functional Groups and Homologous Series in Organic
Chemistry
Following an introduction answering the question WHY is there such a range of organic molecules? there are
sections of styles of representing the structure of organic molecules e.g. molecular formula and molecular
structure. Then examples of functional groups, homologous series, general formula, displayed formula, graphic
formula, molecular formula, skeletal formula, structural formula, empirical formula of molecules etc. are all explained with links to
more examples of structure and naming and quizzes and reaction equations, reaction conditions and mechanisms. Alkanes, Alkenes,Alkynes, Aromatics-arenes, Halogenoalkanes, Alcohols (prim/sec/tert), Phenols, Ethers, Aldehydes, Ketones, Carboxylic acids,
Acid/acyl chlorides, Acid Anhydrides, Acid/acyl Amides, Esters, Nitriles, Amines (prim/tert/sec), Quaternary ammonium salts, Nitro-
aromatics, Diazonium salts and dyes, Sulphonic (sulfonic) acids and a variety possible Aromatic Compounds and Organic Nitrogen
Compounds are also included. At the end is a guide to primary, secondary and tertiary structures i.e. the CLASSIFICATION system for
haloalkanes, alcohols, amines and amides.
Page sub-index:INTRODUCTION* 9.1.1Styles of structure and formula representation*
9.1.2Alkanes,Alkenes,Alkynes,Aromatics-arenes,Halogenoalkanes,Alcohols
(prim/sec/tert), Phenols,Ethers,Aldehydes, Ketones,Carboxylic acids,Acid chlorides,Acid
Anhydrides,Amides,Esters,Nitriles,Amines (prim/tert/sec),Quaternary ammonium salts,Nitro-
aromatics,Diazonium salts and dyes,Sulphonic (sulfonic) acids, Appendix 1Guide to primary, secondary
and tertiary CLASSIFICATION. More examples, due to the variety ofAromatic CompoundsandOrganic Nitrogen Compounds, are on
separate web pages.
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BUT first ... AN INTRODUCTION TO ORGANIC CHEMISTRY i.e. WHY is there such a range of organic molecules and hence why a vast
discipline of organic chemistry?
There are many possible series of organic molecules, so why such variety?
Organic compounds belong to different families, though all organic compounds are based on carbon C, hydrogen
H, and other elements such as oxygen, nitrogen etc.
o The chemistry of the oxides of carbon and carbonates is NOT considered part of organic chemistry.
Most food is chemically organic in nature, apart from some minerals, and many drugs and plastic materials are composed of organic
molecules, consequently, organic compounds and organic chemistry is rather important to us!
The term organic compound comes from the fact that most of the original organic compounds studied by scientists-chemists came from
plants or animals, i.e. of natural origin and contained the 'vital force' of mother nature!
o Historically, for thousands of years, many organic compounds have been used indirectly in herbal preparations for healing and
alleviating symptoms and in food materials such as honey.
o Many natural products have proved precursors for the development of synthetic 'man-made' drugs manufactured by the
pharmaceutical industry.
These days most organic compounds are produced and synthesised from raw materials, in particular the physical separation and chemical
manipulation of the products of fractionally distilling crude petroleum oil.
However, this description of organic chemistry and its historical origins does NOT explain the vast range of organic molecules and their
complex chemistry.
The principal reason why the range of organic molecules is primarily due to the fact that carbon atoms have the ability to link together
by strong covalent bonds to form linear chains, branched chains and cyclic chains and with considerable numbers of
rearrangements to make different molecules of the same formula (isomers).
o Carbon is in Group 4 of the periodic Table with four outer electrons (2.4 or 1s22s
22p
2) which readily pair with electrons from an
atom like oxygen or nitrogen to give four stable covalent bonds (maybe 4 single bonds, 2 single and a double bond, two double
bonds or a triple and a single bond), either way, the normal valency (combining power) of carbon in organic compounds is four.
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o The property of forming chains is called catenation.
o To add to the complexity and variety of organic molecules, carbon can also form stable bonds with other elements,
especially ...
oxygen as in alcohols like ethanol which is used in fuels, as a solvent and combined with organic
acids to make esters used in flavourings and perfumes.
nitrogen as in amines like ethylamine are organic bases and form alkaline solut ions when dissolved
in water.
nitrogen and oxygen in amino acids like aminoethanoic acid which is found combined with other
amino acids in proteins.
halogens as in bromoethane is an 'intermediate' compound and used in the organic
synthesis of more complex organic compounds.
and sulfur & phosphorus etc. by substituting a hydrogen atom with another element or group of atoms compared to
alkanes like butane which only consists of carbon and hydrogen atoms.
o So, this leads to even more possible 'families' of organic compounds and many more individual different molecules.
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o There is no limit to the number of different organic molecules that can be made, though only a small percentage of them
would be useful.
The molecular formula represents a summary of all the atoms in the molecule and a general formula sums up the
formulae a series of compounds e.g. a homologous series of chemically similar compounds.
More on these terms later, but you need their basic definition to appreciate the next point I'm making.
Just to give you an idea of the limitlessness of organic chemistry, using some simple molecular formulae and general
formulae, consider the table below of the number of molecules which can theoretically exist for a given molecular formula
e.g. ifn = 5 for the number of carbon atoms in the molecular formula you get ...
alkanes of molecular formula C5H12
alkenes/cycloalkanes of formula C5H10
alcohols/ethers of formula C5H12O
and amines of formula C5H13N
Some of these numbers have been worked out using a computer program i.e. an algorithm to compute
possible numbers of molecules of a given general formula given a set of rules based on valencies.
o
Number of carbon atoms n in
the general formula below4 5 6 7 8 9 10 11 12
examples of homologous series with this
general formula
CnH2n+2 2 3 5 9 18 35 75 159 355 alkanes
CnH2n 3 5 13 27 66 153 377 ~915 ~2300 alkenes, cycloalkanes
CnH2n+2O 7 14 32 72 171 405 989 ~2430 ~6070 alcohols, ethers
CnH2n+3N 8 17 39 89 211 507 1238 3057 ? amines
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o As the number of carbon atoms increases the number of possible arrangement of the atoms increases
dramatically even for molecules just containing carbon and hydrogen.
o Once you substitute a hydrogen atom for another element or group of atoms, there is a bewildering number of
possibility of molecular structures.
o The fact that life, as far as we know it, is based on carbon chemistry, and we do not know of another element from which the same
huge variety of stable molecules can be me made.
Even unstable organic molecules can be synthesised and manipulated in the laboratory and biochemistry is based on the
thousands of molecules that exist in living systems e.g. sugars, proteins (tissue, enzymes etc.), RNA, DNA, fats like lipids
etc. etc. etc.!!!.
In one of the simplest living cells like an E coli cell, there may be 5000 different compounds, most of them organic
molecules! (e.g. as many as 3000 proteins and 1000 nucleic acids i.e. RNA/DNA molecules)
The compounds in each family have a similar chemical structure and a similar chemical formula and each family of organic compounds
forms what is called ahomologous series.
o As pointed out, different families arise because carbon atoms readily join together in chains (catenation) and strongly bond with
other atoms such as hydrogen, oxygen and nitrogen.
o The result is a huge variety of 'organic compounds' which can be classified into groups of similar compounds i.e. these different
homologous series.
A homologous series is a family of compounds which have a general formula* and have similar chemical properties because they
have the same functional group of atoms
o e.g. C=C alkene, C-OH alcohol or -COOH carboxylic acid etc.
o A functional group is an atom or combination of atoms which gives an organic molecule its distinctive and characteristic
chemistry.
o The term 'functional' group is linked to the concept of a homologous series.
o A homologous series is a group of molecules with the same general formula and the same functional group.
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o They have similar physical and chemical properties such as appearance, melting/boiling points, solubility etc (albeit with tr ends
e.g. increasing boiling point with increasing carbon chain length i.e. increase in molecular mass).
The terms higher/lowerrefer to a larger/smallerorlonger/shorter carbon chains.
The molecular formula represents a summary of all the atoms in the molecule e.g. butane is C4H10 and can be derived from a general
formula - which is explained in the next section 9.1.1
9.1.1 Note on structure 'styles' of representation
An empirical formula is the simplest whole number ratio of the atoms in a compound as found by experiment i.e. chemical analysis. It gives no
structural information and may or may not be the same as the molecular formula e.g. CH4 is both the empirical formula and the molecular formula
of methane. However, the molecular formula of the butane molecule is C4H10 but its empirical formula is C2H5. The molecular formula of a glucose
sugar molecule is C6H12O6 but its empirical formula is only CH2O !
A molecular formula e.g. C3H6O2, gives a summary of all the atoms in the molecule, but gives no information on structure.
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A structural formula - minimal/abbreviated/shortened e.g. or gives a 'limited' structure of a molecule but
unambiguous in terms of interpreting ALL atom-atom links and no/some individual bonds may be shown.
A structural formula - full/displayed/graphical e.g. where all the individual atoms and bonds are shown.
However it can be acceptable to show some side-chain groups in an abbreviated form e.g. methylpropane
where the side-chain methyl group may be written in the abbreviated form, but take car in exams!
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A structural displayed formula with full 3D spatial representation e.g. which shows the shape of the molecule and implies
bond angles (in this case all are 109o). The 'dotted line' bond is behind the plane of the screen/paper/page and the 'wedge' bond is towards you.
The other two thin line bonds are in the plane of the screen/paper/page etc. This gives a good impression of the real shape of the molecule in
terms of the directional covalent bonds and all bond angles here are ~109
o
.
A skeletal formula e.g. in which none of the H atoms bonded to carbon atoms are shown. The lines represent either carbon-carbon
bonds (single, double or triple), but other lines are needed to show bonds to other atoms which are NOT carbon or hydrogen e.g. C-Cl in
and hydrogen atoms are shown if they are bonded to non-carbon atoms e.g. the C-OH in .
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A general formula sums up the formulae a series of compounds e.g. a homologous series of chemically similar compounds with closely related
formulae e.g. the only difference may be more/less -CH2- groupings in the carbon longest chain. There are many examples quoted throughout the
rest of this page in the style CxHyOz etc. where x, y and z are integer variables like 1, 2, 3 etc. but they related for a particular homologous series
e.g. for saturated non cyclo alkanes the general formula is
CnH2n+2 for alkanes, so that n=1 generates the formula for methane CH4 and n=5 generates the formula for pentane C5H12 etc. and .....
CnH2n+1COOH is the general formula for monocarboxylic acids, so that n=0 generates the formula for methanoic acid HCOOH and n=4 generates
the formula for pentanoic acid CH3CH2CH2CH2COOH (so do not assume n always indicates the total carbon atoms in a molecule!).
However in all cases, the IUPAC systematic name is derived from the longest carbon chain, so both meth... (for one carbon) and pent... (for f ive
carbons) occur in the names of the examples above.
FUNCTIONAL GROUPS and HOMOLOGOUS SERIES
Summary of nomenclature, structure and representation in pictures-graphics
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9.1.2 ALKANES or cycloalkanes HYDROCARBONS (saturated)
ANE, e.g. ALKANES, saturatedhydrocarbons i.e. no double or triple bonds.
They can be linear, branched, cyclo, substituted etc. (see later - haloalkanes etc.)
butane, pentylcyclohexane, cyclopropane
2,2-dimethylpropane, 2,2,3-trimethylbutane
Exemplar homologous series: CnH2n+2for non-cyclo alkanes (n=1,2,3 etc.)
and CnH2nforcycloalkanes (n=3,4,5 etc.)isomeric with non-cyclo alkenes
further Notes and examples of the structure and nomenclature of alkanes
Multiple choice Quiz on naming alkanes
Type in an alkane name short answer QUIZ
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Notes on selected reactions of alkanes from a mechanistic point of view but giving general equations and reaction
conditions too
9.1.3 ALKENE HYDROCARBONS (unsaturated)
ENE, ALKENES, unsaturatedhydrocarbons with a carbon=carbon C=C double bond functional group (ene)
They can have more than one C=C, be linear, branched, cyclo
pent-1-ene, 3-ethylpent-1-ene, cyclobuta-1,3-diene
or buta-1,3-diene, cyclohexene
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further Notes and examples of the structure and nomenclature of alkenes
Multiple choice Quiz on naming alkenes
Type in an alkene name short answer QUIZ
Exemplar homologous series: CnH2nfor non-cyclo alkenes (n=2,3 etc. with one C=C bond) isomeric with cycloalkanes
and CnH2n-2forcycloalkenes (n=3,4,5 etc., and with one C=C bond)
Notes on selected reactions of alkenes from a mechanistic point of view but giving general equations and reaction
conditions too
9.1.4 ALKYNE HYDROCARBONS (unsaturated)
YNE e.g. ALKYNES, unsaturated hydrocarbons with a C C triple bond functional group (yne) e.g.
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ethyne, and propyne
Exemplar homologous series: CnH2n-2for non-cyclo alkynes (with one triple bond)
9.1.5 AROMATIC HYDROCARBONS (unsaturated)
'ARENES' are aromatic hydrocarbons with at least one benzene ring functional groupe.g.
or benzene, or methylbenzene
further Notes and examples of the structure and nomenclature of aromatic compounds
further Notes and examples of aromatics
Type in an aromatic name short answer QUIZ
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Notes on selected reactions of aromatic compounds (arenes) from a mechanistic point of view but giving general equations and
reaction conditions too
9.1.6 aliphatic/aromatic HALOGEN COMPOUNDS
Aliphatic: HALO e.g.HALOGENOALKANES (HALOALKANES)
C-X halogen functional groupwhere X = F fluoro, Cl chloro.., Br bromo or I iodo
X is named as a prefixsubstituent in any type of organic molecule from alkanes to carboxylic acids.
chloromethane, bromoethane, dichlorodifluoromethane
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1-bromo-1-chlorobutane, iodocyclohexane
1,2-dibromocyclopentane, chloromethylbenzene
or phenylchloromethane, which can also be classified as an aromatic compound
BUT the halogen is not attached directly to the benzene ring so it is not an aryl halide)
Exemplar homologous series: CnH2n+1Xfor non-cyclo saturated halogenoalkanes (X=F,Cl,Br,I and n=1,2,3 etc.)
and CnH2n-1Xfor saturated cyclohalogenoalkanes (n=3,4,5 etc. with one C-X bond)
A sub-CLASSIFICATION based on structural differences, which can have chemical consequences on e.g. rate of reaction or products
formed in a reaction.
o Halogenoalkanes are classified according to the atoms/groups attached to the carbon of the halogen atom X.
o Primary halogenoalkanes have the structure R-CH2-X, R = H, alkyl, aryl etc. i.e. apart from chloromethane they have one
alkyl/aryl group attached to the C of the C-X group.
e.g. chloroethane CH3CH2Cl
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o Secondary halogenoalkanes have the structure R2CH-X, R = alkyl or aryl etc. i.e. they have two alkyl/aryl groups attached to
the C of the C-X group.
e.g. 2-bromobutane CH3CHBrCH2CH3
o Tertiary halogenoalkanes have the structure R3C-X, R = alkyl or aryl etc. i.e. they have three alkyl/aryl groups attached to the
C of the C-X group.
e.g. 2-iodo-2-methylpropane (CH3)3CI
further Notes and examples of the structure, classification and nomenclature of primary, secondary and tertiary haloalkanes - 3
linked pages
Multiple choice Quiz on naming haloalkanes
Type in a haloalkane name short answer Quiz
Notes on selected reactions of halogenoalkanes (haloalkanes) from a mechanistic point of view but giving general equations and
reaction conditions too
NOTE: Aromatic HALO ... ARENES (aromatic halogen compounds) have the halogen atom directly attached to the benzene ring.
chlorobenzene, 1,4-dichlorobenzene, chloro-2-methylbenzene
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9.1.7 ALCOHOLS (aliphatic, alkanols) and PHENOLS (aromatic)
Aliphatic OH hydroxy functional group (ol) e.g. ALIPHATIC ALCOHOLS. Aliphatic alcohols are classified as primary, secondary and tertiary.
You can have diols, triols etc, with 2,3 etc, OH groups.
If there is a 'higher ranking' functional group in the molecule the substituent OH is called by the prefix 'hydroxy' see * examples.
Primary aliphatic alcohols R-OH where R is alkyl
ethanol, ethan-1,2-diol
or 3-methylbutan-1-ol
4-hydroxybutanoic acid*
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Secondary aliphatic alcohols R-CH(OH)-R' where R or R' are both alkyl (or aryl):
propan-2-ol, butan-2-ol, cyclohexanol, pentan-3-ol
cyclopentanol, 2-hydroxybutanoic acid*
Tertiary aliphatic alcohols RR'R"C-OH where R,R' or R" are all alkyl (or aryl):
or 2-methylpropan-2-ol, 2-methylbutan-2-ol
or 3-methylpentan-1-ol
Exemplar homologous series: CnH2n+1OHfor saturated non-cyclic aliphatic alcohols (n=1,2,3 etc.)
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or the less informative CnH2n+2Oisomeric with aliphatic non-cyclo ethers
and CnH2n-1OHforcycloalcohols (n=3,4,5 etc. with one C-OH)
Notes and examples of the structure and nomenclature of aliphatic alcohols/alkanols
Multiple choice Quiz on naming alcohols
Type in an alcohol name short answer QUIZ
Notes on selected reactions of alcohols from a mechanistic point of view but giving general equations and reaction conditions too
AROMATIC PHENOLS ROH, R=aryl only, when the -OH functional group is attached directly to a benzene ring the molecule is called a phenol.
If there is a 'higher ranking' functional group in the molecule the substituent OH is called by theprefix 'hydroxy' see * example.
or or phenol, 2-chlorophenol, 3-methylphenol
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2,5-dichloro-4-methylphenol, 3-hydroxybenzoic acid*
9.1.8 ETHERS
Alkyl/arylOXYalkane/arene e.g.ETHERS which have the C-O-C linkage.
The smaller carbon chain with the oxygen atom, is given the prefix in the name alkyl/aryl..oxyane
(alkyl-O- groups like CH3-O- are called alkoxy groups).
methoxymethane, methoxyethane, 2-ethoxypropane
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ethoxyethane, 2-methoxypropane,
Exemplar homologous series: CxH2x+1-O-CyH2y+1for saturated non-cyclo ethers (x or y =1,2,3 etc.)
or the less informative CnH2n+2O(n=2,3,4 etc.) isomeric with non-cyclo aliphatic alcohols
orCnH2nO forcycloethers (n=2,3,4 etc. with one C-O-C linkage, non shown at the moment)
further Notes and examples of ethers and isomeric alcohols
9.1.9 ALDEHYDES and KETONES(a group of carbonyl compounds)
AL e.g. ALDEHYDES have the -CHO functional group at the end of a carbon chain e.g.
ethanal, propanal, or 2-methylpropanal
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butanal, pentanal, 2-methylbutanal
Exemplar homologous series: CnH2n+1CHOfor aliphatic aldehydes (n=0,1,2 etc.)
or the less in formative CmH2mO (m=1,2,3 etc.)isomeric with ketonesand saturated cyclic aliphatic ethers
further Notes and examples of the structure and nomenclature of aldehydes
multiple choice Quiz on naming aldehydes/ketones
type in name short answer QUIZ on naming aldehydes/ ketones
Notes on selected reactions of aldehydes/ketones from a mechanistic point of view but giving general equations and reaction
conditions too
ONE e.g. KETONES have the C-CO-C functional group linkage within the carbon chain:
propanone, or butanone, pentan-2-one
or pentan-3-one
http://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDES -
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Exemplar homologous series: CxHxn+1-CO-CyH2y+1for aliphatic ketones (x or y = 1,2,3, etc.)
or the less informative CnH2nO(n=3,4,5 etc.) isomeric with aldehydesand saturated cyclic aliphatic ethers
further Notes and examples of the structure and nomenclature of ketones
multiple choice Quiz on naming aldehydes/ ketones
type in name Quiz on naming aldehydes/ ketones
Notes on selected reactions of aldehydes/ketones from a mechanistic point of view but giving general equations and reaction
conditions too
9.1.10 CARBOXYLIC ACIDS
OIC ACID e.g. CARBOXYLIC ACIDS with the -COOHfunctional group, substituents quoted as prefixes (dioic if 2 -COOH groups) e.g.
aliphatic carboxylic acids
http://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDEShttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/OrgMechs3.htm#ALDEHYDEShttp://www.docbrown.info/page06/WMtestsNotes/aldketQsa.htmhttp://www.docbrown.info/page06/WMtestsNotes/aldketQmc.htmhttp://www.docbrown.info/page06/AldehydesKetones.htmhttp://www.docbrown.info/page06/FunctionalGroups.htm#ALDEHYDES -
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methanoic acid, propanoic acid, *aminoethanoic acid
2-methylpropanoic acid, *2-hydroxybutanoic acid
pentanoic acid, *ethanedioic acid
* examples of a dicarboxylic acids
If there is a 'higher ranking' functional group in the molecule the
substituent OH/NH2 is called by the prefix 'hydroxy/amino see * examples.
Exemplar homologous series: CnH2n+1COOHfor saturated aliphatic mono carboxylic acids (n=0,1,2,3 etc.)
or the less informative CnH2nO2(n=1,2,3,4 etc.)isomeric with aliphatic esters
aromatic carboxylic acids (-COOH directly attached to the ring)
http://www.docbrown.info/page06/FunctionalGroups.htm#ESTERShttp://www.docbrown.info/page06/FunctionalGroups.htm#ESTERShttp://www.docbrown.info/page06/FunctionalGroups.htm#ESTERShttp://www.docbrown.info/page06/FunctionalGroups.htm#ESTERShttp://www.docbrown.info/page06/FunctionalGroups.htm#ESTERShttp://www.docbrown.info/page06/FunctionalGroups.htm#ESTERS -
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* 3-hydroxybenzoic acid, 2-ethanoylhydroxybenzoic acid (Aspirin!)
2-chlorobenzoic acid, * benzene-1,2-dicarboxylic acid
(sometimes carboxylic rather than oic is used e.g. the dicarboxylic acids of benzene)
further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
multiple choice QUIZ on naming RCOOH acids/derivatives
Type in name short answer QUIZ on naming RCOOH acids/derivatives
http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htm#1. -
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9.1.11 ACID ANHYDRIDES
OIC ANHYDRIDE e.g. CARBOXYLIC ACID ANHYDRIDES with the RCO-O-RCO linkage e.g.
or ethanoic anhydride
or pentanoic anhydride
Exemplar homologous series: (CnH2n+1CO)2Oderived from aliphatic mono carboxylic acids (n=2,3 etc.)
further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
multiple choice QUIZ on naming RCOOH acids/derivatives
Type in name short answer QUIZ on naming RCOOH acids/derivatives
http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htm#1. -
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9.1.12 ACID or ACYL CHLORIDES
OYL CHLORIDE e.g. CARBOXYLIC ACID or ACYL CHLORIDES with the -COCl functional group e.g.
or propanoyl chloride, butanoyl chloride
or pentanoyl chloride, benzoyl chloride
Exemplar homologous series: CnH2n+1COClderived from aliphatic mono carboxylic acid chlorides (n=1,2,3 etc.)
further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
multiple choice QUIZ on naming RCOOH acids/derivatives
Type in name short answer QUIZ on naming RCOOH acids/derivatives
http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs.htm#1.http://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page06/RCOOHderivs.htm#1. -
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Notes on selected reactions of acid/acyl chlorides from a mechanistic point of view but giving general equations and reaction
conditions too
9.1.13 ACID AMIDES
AMIDE e.g. CARBOXYLIC ACID AMIDES with the -CONH2 functional group e.g.
or ethanamide, propanamide
butanamide, pentanamide, benzamide
Exemplar homologous series: CnH2n+1CONH2derived from aliphatic mono carboxylic acid amides (n=0,1,2,3 etc.)
http://www.docbrown.info/page06/OrgMechs3.htm#Acylhttp://www.docbrown.info/page06/OrgMechs3.htm#Acylhttp://www.docbrown.info/page06/OrgMechs3.htm#Acylhttp://www.docbrown.info/page06/OrgMechs3.htm#Acylhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/FunctionalGroups.htmhttp://www.docbrown.info/page06/OrgMechs3.htmhttp://www.docbrown.info/page06/OrgMechs3.htm#Acylhttp://www.docbrown.info/page06/OrgMechs3.htm#Acyl -
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further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
and also other organic nitrogen compounds
multiple choice QUIZ on naming RCOOH acids/derivatives
Type in name QUIZ on naming RCOOH acids/derivatives
9.1.14 ESTERS
alkyl/arylOATE e.g. ESTERS of CARBOXYLIC ACIDS derived from ALCOHOLS or PHENOLS.
Esters have the -COOC- linkage:
methyl methanoate, propyl propanoate
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ethyl propanoate, ethyl benzoate
Exemplar homologous series: CxH2x+1-COO-CyH2y+1simple saturated aliphatic esters (x=0,1,2, etc. and y=1,2,3 etc.)
or the less informative CnH2nO2(n=2,3,4 etc.)isomeric with carboxylic acids
further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
multiple choice QUIZ on naming RCOOH acids/derivatives
Type in name QUIZ on naming RCOOH acids/derivatives
9.1.15 NITRILES
The nitrile functional group consists of a carbon to nitrogen triple bond.
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The name is based on the longest carbon chain, including the C of the nitrile group e.g.
methanenitrile, , ,
ethanenitrile, , , , , ,
propanenitrile, , , , , ,
Exemplar homologous series: CnH2n+1CNderived from aliphatic mono carboxylic acid chlorides (n=0,1,2,3 etc.)
further Notes and examples of the structure and nomenclature of carboxylic acids and their derivatives
and also other organic nitrogen compounds
9.1.16 AMINES
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PRIMARY AMINES 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), , , ,
ethylamine (aminoethane), , , ,
Exemplar homologous series: CnH2n+1NH2for saturated mono primary amines (n=1,2,3 etc.)
SECONDARY AMINES have one hydrogen atom and two alkyl or aryl groups attached to the nitrogen
ALIPHATIC: dimethylamine, , ,
ethylmethylamine, ,
diethylamine, ,
TERTIARY AMINES have no hydrogen atom and three alkyl or aryl groups attached to the nitrogen
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ALIPHATIC: trimethylamine, ,
ethyldimethylamine, ,
diethylmethylamine, ,
further examples of the structure and nomenclature of organic nitrogen compounds
9.1.17 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-
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9.1.18 NITRO-AROMATIC COMPOUNDS
These have the nitro -NO2 group directly attached to the ring e.g.
nitrobenzene, ; 1,3-dinitrobenzene,
2-methylnitrobenzene or 1-methyl-2-nitrobenzene,
and also other organic nitrogen compounds
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9.1.19 DIAZONIUM SALTS and AZO DYES
Diazonium salts are formed when primary aromatic amines reaction with nitrous acid
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
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 systeme.g.
reacting (1) with phenol gives
reacting (2) with phenylamine gives
and also other organic nitrogen compounds
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9.1.20 SULPHONIC ACIDS
These molecules have a strongly mono-basic acidic group -SO2OH directly attached to the benzene ring e.g.
benzenesulphonic acid, ,(or benzenesulfonic acid)
2-, 3- or 4-methylbenzenesulphonic acid, , , (or ....sulfonic acid)
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APPENDIX 1 A guide to primary, secondary and tertiary structures
The CLASSIFICATION system for haloalkanes, alcohols, amines and amides
Functional group of the
homologous seriesPRIMARY SECONDARY TERTIARY Comments
HALOALKANES
(halogenoalkanes)
The class of haloalkane can
affect both the rate (reactivity)
and mode (substitution or
elimination) of the reaction
examples of haloalkanes
(halogenoalkanes)
bromoethane2-chloropropane
2-chloro-2-
methylpropane
examples of haloalkanes
(halogenoalkanes)
ALCOHOLS
Phenols are NOT classified in
this way. The ease of oxidation
and nature of product is
affected by the class of the
alcohol
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examples of alcohols
butan-1-ol
propan-2-ol 2-methyl-propan-2-ol
examples of alcohols
AMINES
There are prim/sec/tert aliphatic
(alkyl) or aromatic (aryl) amines.
See also Note 3. below the
table.
aliphatic amine
examples
ethylamineethylmethylamine
triethylamine
aliphatic amine examples
aromatic amine
examples
phenylaminediphenylamine
N,N-diethylphenylamine
aromatic amine examples
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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-phenylbenzamide N,N-dimethylethanamide
examples of amides
******************************
*
***************************************
*
NOTES
1. Abbreviations commonly used: prim or1o (primary), sec or2o (secondary) and tert or3o (tertiary)
2. R and R' do not have to be the same i.e. -R2 could mean -RR' and -R3 could mean -RR'R"
3. amines can form a quaternary ammonium ion
o e.g. in the salt tetramethylammonium chloride, (CH3)4N+
Cl-
4. -
-
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