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
http://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics/AromaticQsa.htmhttp://www.docbrown.info/page07/Aromatics.htmhttp://www.docbrown.info/page07/Aromatics.htm


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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
http://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/OrgMechs2.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQsa.htmhttp://www.docbrown.info/page06/Ahaloalkanes/haloalkaneQmc.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htmhttp://www.docbrown.info/page06/halogenoalkanes1.htm


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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.)



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.)



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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and also other organic nitrogen compounds


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
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/page07/orgNcmpds.htmhttp://www.docbrown.info/page07/orgNcmpds.htmhttp://www.docbrown.info/page07/orgNcmpds.htmhttp://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/page07/orgNcmpds.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/page07/orgNcmpds.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/page07/orgNcmpds.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/page07/orgNcmpds.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/page07/orgNcmpds.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/page07/orgNcmpds.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/page07/orgNcmpds.htmhttp://www.docbrown.info/page06/RCOOHderivs.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQsa.htmhttp://www.docbrown.info/page06/RCOOHderivs/RCOOHderivsQmc.htmhttp://www.docbrown.info/page07/orgNcmpds.htmhttp://www.docbrown.info/page06/RCOOHderivs.htm#1.


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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



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.)



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,

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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

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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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Summary of Homologous Series

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