New Way Chemistry for Hong Kong A-Level Book 3A 1 Nomenclature & Introduction of Major Families of...

New Way Chemistry for Hong Kong A-Level Book 3A1

Nomenclature Nomenclature & Introduction & Introduction

of Major of Major Families of Families of

Organic Organic CompoundsCompounds


Classification of Classification of HydrocarbonsHydrocarbons

alkadienes, etc.

cycloalkadienes, etc.

Huckel rule


Organic compounds containing carbon and hydrogen only.

1.1. HydrocarbonsHydrocarbons


(a)(a) Alkanes (CAlkanes (CnnHH2n+22n+2))

Alkanes are hydrocarbons that contain only C – C and C – H single bonds(except CH4)

Relatively inert as the bonds are strong

saturated hydrocarbons

contain the maximum possible number of hydrogen atoms per molecule


The first 10 members of the unbranched (acyclic) alkane series are :

CH4 Methane C6H14 Hexane

C2H6 Ethane C7H16 Heptane

C3H8 Propane C8H18 Octane

C4H10 Butane C9H20 Nonane

C5H12 Pentane C10H22 Decane


Cycloalkanes are alkanes in which all or some of the carbon atoms are arranged in a ring


Cycloalkanes in skeletal forms

Most stable due to less angle strain

Angle strain arises from repulsions between adjacent bond pairs


Cycloalkanes in skeletal forms


Alkanes and CycloalkanesAlkanes and Cycloalkanes

• General formula of acyclic alkanes: CnH2n+2

• General formula of cycloalkanes: Q.1

CnH2n


The First Three Members of The First Three Members of Alkanes Alkanes

Methane (CH4)

Ethane (CH3CH3)

Propane(CH3CH2CH3)


Starting from C4H10, two or more structures are possible for the same molecular formula.

This phenomenon is called isomerism.

The different structures with the same molecular formula are called isomers.


Q.2 C4H10

H3C

H2C

CH2

CH3

H3C

CH

CH3

CH3

All carbon atoms are sp3 hybridized - zigzag


Q.2 C5H12

H3C

H2C

CH2

H2C

CH3

H3C

CH

CH2

CH3

CH3

H3C

C

CH3

CH3

CH3


Q.2 C6H14


Nomenclature Nomenclature of Alkanesof Alkanes

IUPAC Conventions


Straight-Chain Straight-Chain Alkanes Alkanes

NameNumber of

carbon atomsCondensed

structural formula

Methane

Ethane

Propane

Butane

Pentane

Hexane

Heptane

Octane

Nonane

Decane

1

2

3

4

5

6

7

8

9

10

CH4

CH3CH3

CH3CH2CH3

CH3(CH2)2CH3

CH3(CH2)3CH3

CH3(CH2)4CH3

CH3(CH2)5CH3

CH3(CH2)6CH3

CH3(CH2)7CH3

CH3(CH2)8CH3


Branched-Chain Branched-Chain Alkanes Alkanes 1. Name the longest possible straight

chain

give the parent name for the alkane


Branched-Chain Branched-Chain Alkanes Alkanes 2. Name the substituent groups – the

branchesCnH2n+1– Alkyl groups (derived from alkanes)

CH3 – methyl

C2H5 – ethyl


C3H7 –

H3C

H2C

CH2

propyl

H3C

CH

H3C

isopropyl


C4H9 –

H3C

H2C

CH2

H2C

butyl

H3C

CH

H2C

CH3

sec-butyl

secondary, 2 carbon

CH CH2

H3C

H3C

isobutyl

C

H3C

H3C

H3C

tert-butyl

tertiary, 3 carbon


3. Number the positions of the substituent groups with the smallest possible numbers

2

2-methyl

2-methylbutane


4. If more than one substituent group of the same kind exist, the numbers are denoted by prefixes.

2 di

3 tri

4 tetra

5 penta

6 hexa


tetramethyltetramethylmethane


propane

2

2,2-dimethylpropane


Cl

Cl

Cl

1 5

1,5,5-trichloro

1,5,5-trichlorohexane


Cl

Cl

Cl

1 5

1,5,5-trichloro

2,2,6-trichloro

6 2

‘Lowest numbers’ does NOT refer to the smallest sum


5. If two or more different substituent groups exist, they are named in alphabetical order but NOT in numerical order of their positions.

23

2,2-dimethyl

3-ethyl

3-ethyl-2,2-dimethylpentane

prefix is not considered


3-ethyl-2,2-dimethylpentane

3

3-tert-butylpentane

tert-butyl


(b)(b) Alkenes (CAlkenes (CnnHH2n2n))

One C=C double bond

More reactive than alkanes due to weaker bond

unsaturated hydrocarbons

NOT contain the maximum possible number of hydrogen atoms per

molecule



First member is ethene (ethylene)

Cyclic structures are possible

cyclopropene

cyclobutene



First member is ethene (ethylene)

Cyclic structures are possible

cyclopentene

cyclohexene

Q.3

CnH2n-2


Starting from C4H8, isomerism occurs

Structural isomerism :

• same molecular formula

• different linking orders of atoms


Structural isomeris

m

Chain isomerism

Position isomerism

Functional group

isomerism

Different carbon

skeletons

Functional groups in different positions

Different functional

groups


Stereoisomerism

Geometrical isomerism

Optical isomerism

Same linking order of atoms

Different spatial arrangements of

atoms


Geometrical IsomerismGeometrical Isomerism

e.g. cis-but-2-ene and trans-but-2-ene


Both substituent groups are on the same side w.r.t. the axis of the C=C double bond

Both substituent groups are on the opposite sides w.r.t. the axis of the C=C double bond


cannot be inter-converted at lower

temperatures


Rotation about the axis of a double bond through an angle of 90o results in the breaking of the π

bond

maximum overlap of pz orbitals

minimum overlap of pz orbitals


Arises from restricted rotation about the axis of the C=C double bond.



Q.4 Position isomers

Chain

isom

erism

position isomers

Geometrical isomers

trans cis


Q.4 Position isomers

Chain

isom

erism


Q.4

Functional group isomerism


Q.4

Chain isomerism

A total of 11 isomers


Q.4 C5H8

C5H6


pent-1-ene1

pent-2-ene2


2

pent-2-ene

(2E)-pent-2-ene

(2Z)-pent-2-ene


trans

cis


E/Z notation

If there are three or four different groups attached to the C atoms of C=C double

bond

E/Z notation rather than the cis/trans notation is used to name the stereoisomers of a molecule.

E : in opposition to trans

Z : together cishttp://en.wikipedia.org/wiki/Cahn-Ingold-Prelog_priority_rule


CH3

CH3

CH3

(2Z)-3-methylpent-2-ene

CH3 CH3

CH3

(2E)-3-methylpent-2-ene

1

2 3

1

2 3


2-methylbut-1-ene

2-methylbut-2-ene

3-methylbut-1-ene

2

2

1

3 1

Functional group has a higher priority than branches

Q.4


cyclopentane

methylcyclobutane

Q.4


Q.4

ethylcyclopropane

1,2-dimethylcyclopropane

1,1-dimethylcyclopropane


bicyclo[2.1.0]pentane

bicyclo[1.1.1]pentane

spiro[2.2]pentane

Polycyclic hydrocarbons contain two or more rings that share two or more

carbon atomsA spiro compound is a bicyclic compound with rings connected through just one atom


tricyclo[2.1.0.01,3]pentane

tricyclo[1.1.1.11,3]hexane


(c)(c) Alkynes (CAlkynes (CnnHH2n-22n-2))

One CC triple bond

Reactive (unsaturated) due to weak bonds

First member is ethyne (acetylene), C2H2

Cycloalkenes and alkadienes have the same general formula as alkynes


(c)(c) Alkynes (CAlkynes (CnnHH2n-22n-2))

C atoms in triple bond are sp hybridized

Linear

Cyclic structures are highly unstable

due to great angle strain90 << 180


In naming alkenes and alkynes,

the ‘longest’ carbon chain need NOT be the one that contains the multiple bond.

1

2

2-ethylpent-1-ene


In naming alkenes and alkynes,

the ‘longest’ carbon chain need NOT be the one that contains the multiple bond.

13

3-methylenehexane


(2E)-5-methylhex-2-ene

Functional group has the higher priority than branch.

25

Q.5(a)


13

(3E)-penta-1,3-diene

Q.5(b)


Q.5(c)

3

14

52

1

2

4

5

3

1,3 > 2,4


3

1

(3E)-pent-3-en-1-yne

NOT ene

Q.5(c)


Q.5(d)

31

452

12 4

5

3

1,3 > 2,4although -yne has the smaller

number


pent-1-en-3-yne

NOT ene

Q.5(d)

31

452


14

1

4

pent-4-en-1-yne

pent-1-en-4-yne

If the same set of numbers is obtained by counting in either direction, the number is assigned in alphabetical order. Refer to 5(i)

Q.5(e)


1

8

8

diene has a higher priority than enyne

If the enyne chain is longer, enyne > diene

The length of C chain is more important !

Q.5(f)


1

8

34 5 6

7

octa-1,6-diene

5-ethyl

6-ethynyl

3,7-dimethyl

4-methylidene5-ethyl-6-ethynyl-3,7-dimethyl-4-methylideneocta-1,6-diene

Q.5(f)


1

8

67

8

octa-1,6-diene

octa-1,7-diene

Q.5(g)


1

8

63 4 5

7

octa-1,6-diene

5-ethyl

6-vinyl

3,7-dimethyl

4-methylidene

5-ethyl-3,7-dimethyl-4-methylidene-6-vinylocta-1,6-diene

Q.5(g)


1

863 4 5

7

octa-1,7-diene substituents at 3,4,5,6

Q.5(h)


1

86 34

57


Q.5(h)


1

8

63 4 5

7

octa-1,7-diene substituents at 3,4,5,6,7

Q.5(h)


octa-1,7-diene substituents at 2,3,4,5,6

1

86 345

72

Q.5(h)


Q.5(h)

octa-1,7-diene

4-ethyl

3-ethenyl

2,6-dimethyl5-methylidene

3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene

1

86 345

72

vinyl methylene


1

23 4 5 6

7

8


Q.5(i)


8

76 5 4 3

2

1


Q.5(i)


1

23 4 5 6

7

8

octa-1,7-diene substituents at 3,4,5,65-ethyl3,6-dimethyl4-methylidene

Q.5(i)


8

76 5 4 3

2

1

octa-1,7-diene substituents at 3,4,5,64-ethyl3,6-dimethyl5-methylidene

4,3,6,5 > 5,3,6,4

4-ethyl-3,6-dimethyl-5-methylideneocta-1,7-diene

Q.5(i)


ethenylcyclohexane

In naming hydrocarbons, cyclic structures always have higher priority than C=C, CC.

ethynylcyclohexane


Also, cyclic structure rather than the length of the carbon chain is first considered.

heptylcyclohexane


but-3-en-1-ylcyclohexane

13

The C directly bonded to the ring is assigned the lowest possible

number

New Way Chemistry for Hong Kong A-Level Book 3A

23



21


In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order.

1

1-ethyl

1-ethyl-2-methylcyclohexane

2 2-methyl



2

1-methyl1

2-(propan-2-yl)

1-methyl-2-(propan-2-yl)cyclohexane

2



1

1-butan-2-yl22-methyl

1-(butan-2-yl)-2-methylcyclohexane


Q.6

1,2-dimethyl-3-(propan-2-yl)cyclopropane

propan-2-ylcyclopropane


Q.6

1 2

3

prop-1-en-1-yl(2-methylprop-1-en-1-yl)

(2-methylprop-1-en-1-yl)cyclobutane


Q.6

1

2

1-methylcyclobutene

2

1

2-methylcyclobutene


Q.6

3-methylcyclobutene

1

23

4-methylcyclobutene

2

14


Q.6

3-methylcyclobutene

1

23

4

12

3


(d)(d) Aromatic hydrocarbonsAromatic hydrocarbons

With a total of (4n + 2) electrons in the conjugated system

(alternating single and double bonds)



Extra stability (aromaticity) due to delocalization of electrons

Also called arenes



C6H5 – phenyl group

C10H7 – naphthyl group

Both are aryl groups


Q.7

6 = 41+2

aromaticmethylbenzen

e


10 = 42+2

aromaticnaphthalene

Q.7


14 = 43+2

aromaticanthracene

Q.7


8 4n+2

NOT aromatic

cyclooctatetraene

Q.7


8 4n+2

NOT aromatic

cyclooctatetraene, 環辛四烯

The molecular is not planar

2pz orbitals are not parallel to one another

poor delocalization of electrons

Q.7

>120o


2.2. Hydroxy compoundsHydroxy compounds

Organic compounds with one or more hydroxyl groups, –OH.


(a)(a) Alkanols (alcohols)Alkanols (alcohols)

Derived from alkanes

Contain one or more –OH groups attached to an alkyl group.

R – OHAlkyl group

Hydroxyl group



Hydroxy derivative of alkane

RH ROH

H replaced

by OH HOH

H replaced

by R

Alkyl derivative of water




General formula : CnH2n+1OH (acyclic)

Three classes :

Primary, 1

Tertiary, 3

Secondary, 2

R C

H

H

OH R C

H

R'

OH R C

R''

R'

OH


Naming of alkanols : -Naming of alkanols : -

The longest C chain containing the –OH group is chosen.

–ane –anol

The position of –OH group is indicated by the smallest possible number.


OH

pentane

1234

5

pentan-2-ol


OH

pentane

12345

pentan-3-ol


OH OH

12 3 4

5

pentanepentane-2,4-diol

‘e’ is retained in diol


(b)(b) PhenolsPhenols

Derived from aromatic hydrocarbons

Contain one or more –OH groups attached to an aryl group

Ar – OHAryl group Hydroxyl

group


phenol

OH OH

OH1

2

2-hydroxyphenolBenzene-1,2-diol


OH

Cl

OH

Cl

OH

Cl

o-chlorophenolo ortho

m-chlorophenolm meta

p-chlorophenolp para

2-chlorophenol 3-chlorophenol

4-chlorophenol

1 1 1

2

3

4


Q.8

OH

1

6

42

4-methylhexan-2-ol

OH

15 4 2 4-methylpentan-2-

ol


OH

123

4

5

- OH has a higher priority than C=C

pent-3-en-2-ol

trans-

(3E)-pent-3-en-2-ol

Q.8


OH

Menthol (薄荷醇 )

cyclohexanol

with

TWO branches

Propan-2-yl

methyl

Q.82


OHmenthol

1

2

4

3

5

OH

1

24

5

36

6

2,5 > 3,6

5-methyl-2-(propan-2-yl)cyclohexanol

Q.8


3.3. EthersEthers

Contain the oxy, –O-, group or

alkoxy, R-O- group

R

O

R

oxy group


3.3. EthersEthers

Contain the oxy, –O-, group or

alkoxy, R-O- group

R

O

R

Alkoxy group


3.3. EthersEthers

Alkyl derivatives of water

H

O

H

R

O

R

2H replaced by 2R


3.3. EthersEthers

Three classes of ethers : -R

O

'R

Ar

O

R

Ar

O

'Ar

H

O

H

a b c 105o

a,b,c,are all greater than 105 due to

stronger van der Waals’ repulsive forces between bulky alkyl/aryl groups than between H atoms


3.3. EthersEthers

Naming : -

The alkoxy groups are always treated as substituents and expressed as prefixes.


Q.9

Omethoxy

ethane

methoxyethane


O

methane

ethoxy

ethoxymethane

Q.9


Obenzene

methoxy

methoxybenzene

Q.9


O

phenoxy

methane

phenoxymethane

Q.9


Opropane

methoxy

2

1

3

2-methoxypropane

Q.9


4.4. Carbonyl compoundsCarbonyl compounds

Organic compounds with the carbonyl group,

C O



(a) Aldehydes

Products of dehydrogenation of alcohols

R C O

H

H

H

R

C

H

O + H2

At least ONE H attached to C

R : alkyl, aryl or H


(a) Aldehydes

Examples : -

H H

O

H

O

H

O

H

O

methanal

ethanal propanal

benzaldehyde

–ane replaced by –anal


(a) Aldehydes

Examples : -

H H

O

H

O

H

O

H

O

methanal

ethanal propanal

benzaldehyde

The aldehye group, –CHO, always occupies the terminal position

No need to specify its position

propan-1-al



(b) Ketones

No H atom is directly attached to the carbonyl group

R

C

'R

O

R, R’ : alkyl or aryl group


O

(b) Ketones

Examples : -

O

propanone butanone

–ane replaced by –anone


(b) Ketones

Examples : -O

O

pentan-2-one pentan-3-one

2

3


(b) Ketones

Examples : -

O O

4-methylpentan-2-one

24 2 3

2-methylpentan-3-one


(b) Ketones

Examples : -O

O

OO

pentane-2,3-dione

pentane-2,4-dione

23 24


5.5. Carboxylic acidsCarboxylic acids

Organic compounds with the carboxyl group,

C

OH

O




C

OH

O

hydroxyl

carbonyl

carboxyl




R C

OH

O

R : alkyl, aryl or H

If R is an alkyl group, the compound is an alkanoic acid, CnH2n+1COOH.


Carboxylic acids

Examples : -

H

OH

O

OH

O

OH

O

methanoic acid

ethanoic acid

propanoic acid

–ane replaced by –anoic acid


Carboxylic acids

Examples : -

H

OH

O

OH

O

OH

O

methanoic acid

ethanoic acid

propanoic acid

The carboxyl group, –COOH, always occupies the terminal position



Carboxylic acids

Examples : -

benzoic acid

COOH COOH

OH

COOH

2-hydroxybenzoic

acid

3-methylbenzoic acid

1

3

1

2


Carboxylic acids

Examples : -

COOH COOH

COOH

benzoic acid

cyclohexanecarboxylic acid

cyclohexylethanoic acid

cyclohexylacetic acid


COOH

HOOC

Carboxylic acids

Examples : -

hexanedioic acid


COOH

HOOC

Carboxylic acids

Examples : -

hexanedioic acid

16

hexane-1,6-dioic acid


COOH

HOOC

Carboxylic acids

Examples : -

hexanedioic acid

1

4




6.6. Acids derivativesAcids derivatives

FOUR types : -

OH replaced by ClR C

OH

O

R C

Cl

O

carboxylic acid acyl(acid) chloride

acyl group



FOUR types : -

R C

O

O

'R C

O

OH

HR C

O

O

C

O

'R

H2O

acid anhydride

R R’ for mixed acid anhydride



FOUR types : -

H2OR C

O

O

H

R'HO+ R C

O

O

R'

esterR : alkyl, aryl or H

R’ : alkyl or aryl



FOUR types : -

R C

OH

O

NH2H+ R C

NH2

O

H2O

1° amideN links to only ONE

C


R C

OH

O

NHH

R'

+


FOUR types : -

R C

HN

O

R'

H2O

2° amide

N links to TWO C atoms

1o amine



FOUR types : -

R C

OH

O

NH

R'

+

R''

H2O

3° amide

R C

N

O

''R

R'

N links to THREE C atoms

2o amine


Naming of acids derivativesNaming of acids derivatives

Acyl chloride : oic acid to oyl chloride

Cl

O

ethanoyl chloride

Or

acetyl chloride



Acyl chloride : oic acid to oyl chloride

Cl

O

ethanoyl chloride

spacing



Acid anhydride : oic acid to oic anhydride

O

O

O

ethanoic anhydride

spacing



Acid anhydride : oic acid to oic anhydride

O

O

O

ethanoic propanoic anhydride

For mixed anhydride, the parent acids are named in

alphabetical order



Ester : oic acid to oate preceded by R group of ROH

O

O methyl

ethanoate

spacing


O

O



ethyl propanoate


O

O



ethyl propenoateOr, ethyl acrylate


O

O



ethyl 2-methylpropenoate2 1 Or

ethyl 2-methylacrylate



Amides : oic acid to amide

NH2

O

ethanamide




HN

O

N-methyl

ethanamide

NO spacing

Or, N-methylacetamide




N

O

N,N-dimethyl

ethanamide


N

O



N-ethyl ethanamide

-N-methyl

Or

N-ethyl-N-methylacetamide


7.7. Halogeno hydrocarbonsHalogeno hydrocarbons

Hydrocarbons containing at least one halogen atom

R – X X : halogens


-F fluoro

-Cl chloro

-Br bromo

-I iodo


Hydrocarbons containing at least one halogen atom

Always treated as substituents (shown by prefixes)



Examples : -

C Br

H

H

H

C Br

H

H

Br

bromomethane dibromomethane



Examples : -

C Br

F

F

F

C F

Br

Cl

F

bromotrifluoromethane

bromochlorodifluoromethane

BTM

BCF

Both are used in fire extinguishers



Examples : -

Br Br

Br

bromobenzene

1,2-dibromobenzene



Examples : -Br

Cl

Br

Cl

1

41

4

1-bromo-4-chlorobenzene

4-bromo-1-chlorobenzene



Examples : -Br

Cl

Cl1

2

4

Br

Cl

Cl

1

2

5

1-bromo-2,4-dichlorobenzene




Examples : -Br

Cl

Cl

1

3

4

Br

Cl

Cl

4

2

1




Examples : -Br

Br

Br

Br

Br

Br

hexabromobenzene


1,1-dichlorobutane

2,2-dichlorobutane

Cl

Cl

Cl

Cl

Q.10

All acyclic structures of C4H8Cl2


Cl

Cl

Cl

Cl

Cl

Cl

Cl

Cl

1,2-dichlorobutane1,3-dichlorobutane

1,4-dichlorobutane

2,3-dichlorobutane

**

* chiral centre, optical isomers exist

Q.10


Cl Cl

1,1-dichloro-2-methylpropane

1

2 3

Q.10

2-(dichloromethyl)propan

e

Cl Cl

12

3


Cl Cl

Cl

Cl

Cl

Cl




1

1

1

2

2

2

3

3

3

Q.10


8.8. AminesAmines

Derivatives of ammonia

NH3

H

N

H

R

H

N

'R

R

''R

N

'R

R

Primary(1°) amine

Secondary(2°) amine

Tertiary (3°) amine


8.8. AminesAmines

Naming amines derived from hydrocarbonsThe amino group, is always treated as the principal functional group and expressed as suffix. e replaced by amine methanami

neethenamine

(ethylenamine)

NH2

NH2

NH2 ethynamine (acetylenamine)


8.8. AminesAmines

Naming amines with functional groups other than CC, C=C, X- and RO-

The amino group, is always treated as the substituent and expressed as prefix, amino-

NH2

HO2-aminoethanol

1

2


8.8. AminesAmines

Examples : -

NH

NH

N-methyl

methanamine

ethanamine

N-methyl

2° amine


8.8. AminesAmines

N

N

3° amine

ethanamine

N,N-dimethyl

methanamine

N,N-dimethyl


8.8. AminesAmines

NH2 NOT benzenamine

phenylamine or aniline


8.8. AminesAmines

NH2

NH2

NH2

2

1

3

4

1

1 2-methylaniline

3-methylaniline

4-methylaniline

or o-toluidine

or m-toluidine

or p-toluidine


8.8. AminesAmines

NH2 2-methylaniline

NH N-methylaniline

N-phenylmethanamine


8.8. AminesAmines

NH2

1-phenylmethanamine


8.8. AminesAmines

NH2

NH2

12

3

32

1

Prop-2-en-1-amine

Prop-1-en-2-amine


8.8. AminesAmines

NH2

NH2

linear 1

23

4

but-3-yne-1,2-diamine


8.8. AminesAmines

NH2

NH

123

propane-1,2-diamine

N2-ethyl


Q.11NH2

OH

NH2

NH2

NH2

COOH

2-aminophenol

benzene-1,2-diamine

2-aminobenzoic acid


Q.11

NH

NH2

123

4

1

234

5

N-methylbutan-1-amine

pentan-2-amine


Q.11

NH2

NH2

1butan-1-amine

2 butan-2-amine


Q.11

HN

NH2

NH

1

23

propane-1,2-diamine

N1-ethylpropane-1,2-diamine

123

4 N-methylbutan-2-amine


N

O

Q.11N-ethyl

ethanamine 2-methoxyN-methyl

1

2

N-ethyl-2-methoxy-N-methylethanamine


N

O

Q.11ethanamine

1

2

N-(2-methoxyethyl)

N-methyl

N-(2-methoxyethyl)-N-methylethanamine

3 substituents > 2 substituents


Q.11

N

O

propan-1-amine1

2

3

1

2

N-(2-methoxyethyl)

N-methyl

N-(2-methoxyethyl)-N-methylpropan-1-amine


Q.11

N

O

12

3 propan-2-amine

1 2

N-(2-methoxyethyl)

N-methyl

N-(2-methoxyethyl)-N-methylpropan-2-amine


9.9. NitrilesNitriles

Containing the cyano group, -CN



Naming : -

If acting as the principal functional group,

it is expressed as the suffix, nitrile

If acting as the substituent,

it is expressed as the prefix, cyano.



Examples : -

C N

C

N

ethanenitrile

1

23

2-methylpropanenitrile

The carbon of the -CN group is counted as part of the longest carbon chain.



Examples : -

C N

C

N

ethanenitrile

1

23

2-methylpropanenitrile

No need to specify its position.

The -CN group always occupies the terminal position.



C

N

OH

12345

4-hydroxypentanenitrile



HOOC

C

N

21 3

propanoic acid

3-cyano-2-methyl

If used as prefix, its carbon is not counted as part of the main carbon chain



HOOC

C

N

21

3

propanoic acid

2-(cyanomethyl)

Only one substituent


10.10. Poly-functional Poly-functional compoundscompounds

With two or more functional groups



With identical functional groups

buta-1,3-diene

buta-1,3-diyne1

1

2

2

3

3

4

4


CH3

CH3

CH3

CH3

CH3

CH3

(2E,4E)-hexa-2,4-diene

(2E,4Z)-hexa-2,4-diene(2Z,4E)-hexa-2,4-diene

(2Z,4Z)-hexa-2,4-diene

＝CH3

CH3

2Z > 2E



OH

O

HO

O

H H

OO

ethanedioic acid

pentanedial

-COOH and –CHO groups always occupy the terminial positions.






NH2

H2N

OOO

hexane-1,6-diamine

heptane-2,4,6-trione




propane-1,2,3-triol

HO OH

OH

12

3


OH OH

OH

OH OH

xylitol

1 2 3 4 5

pentane-1,2,3,4,5-pentol

206



With different functional groups

H2N COOH

COOH

OH

2-aminoethanoic acid

or glycine

2-hydroxypropanoic acid

12

123



With different functional groups

(2E)-hept-2-en-6-yn-1-ol

OH

1

6

2

34

57



Naming : -

1. The functional group with the highest priority (the principal functional group) is expressed as the suffix.


N

+

C

HO

O> >

-OH > -NH2 > CC > C=C > -OR = X

C

H

O C O-CN > > >

O

OO

R

C

RO

O C

X

O C

H2N

O> >> >



Naming : -

2. The main carbon skeleton should be the one that contains the greatest number of principal functional groups.

The main carbon chain needs NOT be the longest one except

3-methylidenehexane

p.5



Naming : -

3. The position(s) of the principal functional group(s) is/are given the lowest possible number(s)

Exception : p.5 Q.5(e)


14

1

4

pent-4-en-1-yne

pent-1-en-4-yne

If the same set of numbers is obtained by counting in either direction, the number is assigned in alphabetical order.

Q.5(e)


(2Z)-3-hydroxypent-2-enoic acid

Worked examples : -

(a)COOH

OH

1234

5

C2 : COOH > H atomic masses are

comparedC3 : OH > CH2C

Z


Worked examples : -

(b)

COOH

OH

linear

12

34

5

(2Z)-3-hydroxypent-2-en-4-ynoic acid

Z

C2 : COOH > HC3 : OH > CC


Worked examples : -

(c)

HOOC COOH

OH

12

34

5

(2Z)-3-hydroxypent-2-enedioic acid

Z

C2 : COOH > HC3 : OH > CH2C


Worked examples : -

(d)

HOOC COOH

OH

O

12

34

5

(3Z)-3-hydroxy-2-oxopent-3-enedioic acid

124

35

(2Z)-3-hydroxy-4-oxopent-2-enedioic acid


HOOC COOH

OH

CN

Worked examples : -

(e)

12

345

(2Z)-4-cyano-3-hydroxypent-2-enedioic acid


Worked examples : -

(f)

C

N

O H

12

345

4-formylpentanenitrile


Worked examples : -

(f)

C

N

O H

4-methyl-5-oxopentanenitrile

12

34

5


COOH

OH

O

H

Worked examples : -

(g)1

2

34

5

Carbonyl C is counted as part of the main carbon

chain3-hydroxy-5-oxopentanoic acid3-hydroxy-4-formylbutanoic acid

The one with the longer C chain is preferred


HOOC COOH

OH

O

OH

Worked examples : -

(h)

5 1234

(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid


HOOC COOH

OH

O

OH

Worked examples : -

(h)

5 1234

(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid

C2 : COOH = CHO;

COOH = CHO;

COOH > CHO

C3 : OH > COC;

Z


Worked examples : -

(i) O

COOH

NH2

12

34

5

5-amino-5-oxopentanoic acid4-(aminocarbonyl)butanoic acid


HOOC COOH

OH

O

NH2O

Worked examples : -

(j)

12345

2-(aminocarbonyl)3-hydroxy

4-oxo

2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid

2A4O > 4A2O


HOOC COOH

OH

O

NH2O

Worked examples : -

(j)

12345

2-(aminocarbonyl)3-hydroxy

4-oxo 2A4O > 4A2OIf the same set of numbers is obtained from either

direction, substituents are numbered in alphabetical order


COOH

O

Cl

Worked examples : -

(k)2

13

45

5-chloro-5-oxopentanoic acid


HOOC COOH

OH

O

ClO

Worked examples : -

(l)

12345

2-(chlorocarbonyl)3-hydroxy

4-oxo

2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid

2C4O > 4C2O


Worked examples : -

(m) COOH

O

O

12

34

5

5-methoxy-5-oxopentanoic acid


HOOC COOH

OH

O

OO

Worked examples : -

(n)

5 1234

2-(methoxycarbonyl)3-hydroxy

4-oxo

3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid


Worked examples : -

(o)COOH

O

OO

12

34

5

5-(ethanoyloxy)-5-oxopentanoic acid


Worked examples : -

(p)HOOC COOH

O O

O

12

34

5

3-carbonyl

3-(oxycarbonyl)3-[(ethanoyloxy)carbonyl]

pentanedioic acid

3-[(ethanoyloxy)carbonyl]pentanedioic acid


HOOC COOH

O

O

O

O

Worked examples : -

(p) 12

34

5

3-carbonyl

3-(oxycarbonyl)3-[(carbonyloxy)carbonyl]

pentanedioic acid

3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid

3-{[(methoxycarbonyl)oxy]carbonyl}


N

COOH

+

Worked examples : -

(q)

ethanaminium ion

N-carboxy-N,N-dimethyl

6B


N

COOH

COOH

+

Worked examples : -

(r)

ethanaminium ion

N,N-dicarboxy-

N-methyl


Propane-1,2,3-tricarboxylic acid

Or

Propane-1,2,3-trioic acid

HOOC COOH

COOH

Worked examples : -

(s) 12

34

51

2

3

3-carboxypentanedioic acid

Citric acid


Worked examples : -

(t)

HOOC COOH

COOH

COOH

32 1

propane-1,1,2,3-tetracarboxylic acid


O

OH

OH

O

OH

O OH

1

2

3

4

5

1,1,5-tricarboxylic acid

5-hydroxypenta-1,4-diene-

(4Z)-

238


COOH

O

H2N

3-amino-3-oxopropanoic acid

Q.12(a)


HOOC COOH

O NH2

3-(aminocarbonyl)pentanedioic acid

Q.12(a)


COOH

O

H

4-oxobutanoic acid

Q.12(b)


HOOC COOH

H O3-formylpentanedioic acid

Q.12(b)


OC

HN

3-oxopropanenitrile

Q.12(c)


N CCOOH

4-cyanobutanoic acid

Q.12(c)


COOH

C

N

4-cyanopentanoic acid

Q.12(c)


HOOC COOH

O O

3-(methoxycarbonyl)pentanedioic

acid

Q.12(d)


O COOH

O

4-methoxy-4-oxobutanoic acid

Q.12(d)


O

O

COOH

3-(acetyloxy)propanoic acid

Q.12(d)


COOH

OCl

5-chloro-4-methyl-5-oxopentanoic acid

Q.12(e)


2-methylpentanedioic acid

4-(chlorocarbonyl)pentanoic acid is wrong since the structure should be viewed as the derivative of 2-methylpentanedioic acid.

COOH

OHO

COOH

OCl

5-chloro-4-methyl-5-oxopentanoic acid

Q.12(e)


HOOC COOH

O Cl

3-(chlorocarbonyl)pentanedioic acid

Q.12(e)


HOOC COOH

OCl

O Br

3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid

Q.12(e)


hexanedioyl dichloride

Q.12(f)

Cl

O

Cl

O


6-bromo-6-oxohexanoyl chloride

Q.12(e)

Cl

O

Br

O

12

34

566

54

32

1

6-chloro-6-oxohexanoyl bromide


HOOC COOH

OCl

O Br


Q.12(e)


HOOC COOH

OCl

O Br


Q.12(e)


Cyclohexylamine

NH2

Q.13(a)


Benzene-1,3-dioic acid

COOH

COOH

1

3

Q.13(b)


OH

HO

(3E)-hept-3-ene-2,5-diol

12

3

5

Q.13(c)


Propane-1,2,3-triol

OH

OHHO

12

3

Q.13(d)


1,2-dichloro-1,1,2,2-tetrafluoroethane

ClCl

F

F

F

F

1 2

Q.13(e)


Methyl 2-methylpropenoate

O

O1

2

Q.13(f)


3-hydroxy-2,4-dioxohex-5-enal

HO

OH

O

O

32 4

51

Q.13(g)


3-ethoxypentanedioic acid

HOOC COOH

O

3

Q.13(h)


OH

Br

Br

COOH

(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid

12

56 4

Q.13(i)


Cyclohexa-2,5-dien-1-ol

OH1

2

5

Q.13(j)


4-bromo-5,5-dichlorocyclohex-2-en-1-ol

OH

ClCl

Br

1

4

5

Q.13(k)


1-butyl-2,4,5-trimethylbenzene

1

2

4

5

Q.13(l)


Pentan-2-ylbenzene

Q.13(m)


CH3 CH3

(2Z)-pent-2-en-2-ylbenzene

CH2 CH3

pent-1-en-2-ylbenzene

CH3


CH3



O

O

HO O

aspirin caffeine

aspirinQ.14

All C atoms are sp2 hybridized


O

O

HO O

aspirin caffeine

Analgesic

O

O

HO O

Ester

carboxylC9H8O4

Q.14


N

N

N

N

H

CH3

O

O

H3C

CH3

Caffeine

Q.14

sp3 hybridized

sp2 hybridized


N

N

N

N

H

CH3

O

O

H3C

CH3

N

N

N

N

H

CH3

O

O

H3C

CH3Tertiary amide

carbonyl

Tertiary amino

Tertiary amino

C=N bond

C=C bond

C8H10N4O2Q.14


HO NH

O

Acetaminophen

Q.14

sp2 hybridized

sp3 hybridized


HO NH

O

Acetaminophen

HO NH

Ohydroxyl

Secondary amide

C8H9NO2

Q.14


HO

HO

NH

OH

Adrenalin

Q.14

sp2 hybridized

sp3 hybridized


HO

HO

NH

OH

Adrenalin

HO

HO

NH

OH

hydroxyl

Secondary amino

C9H13NO3

Q.14


HO

HONH2

Dopamine

A neurotransmitter – A deficiency is associated with Parkinson’s disease

Q.14

sp2 hybridized

sp3 hybridized


HO

HONH2

Dopamine

A neurotransmitter – A deficiency is associated with Parkinson’s disease

HO

HONH2

hydroxylPrimary amino

C8H11NO2

Q.14


OH

Menthol – from peppermint oil

Q.14

sp3 hybridized


OH

Menthol – from peppermint oil

OH

hydroxyl

C10H20O

Q.14


ClCl

Cl

ClCl

DDT

Insecticide

Q.14 sp2 hybridized

sp3 hybridized


ClCl

Cl

ClCl

DDT

Insecticide

ClCl

Cl

ClCl

Chloro

C14H9Cl5

Q.14


HO OH

O

O

phenolphthalein

Q.14

sp2 hybridized

sp3 hybridized


HO OH

O

O

phenolphthalein

HO OH

O

O

hydroxyl

Ester

Q.14

C20H14O4


N

N

nicotine287

Insecticide

Q.14

sp2 hybridized

sp3 hybridized


N

N

N

N

nicotine

Insecticide

Tertiary aminoC=N

Q.14

C10H14N2


2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)

Q.14

sp2 hybridized

O

O

Cl

Cl

Cl

Cl

dioxin


O

O

Cl

Cl

Cl

Cl

290

One of the most toxic chemical known – A class 1 carcinogen Ether

Chloro Chloro

C12H4O2Cl

4

Q.14


N

O

NH

O

OHO

O

Anti-hypertensive

Q.14

sp2 hybridized

sp3 hybridized


N

O

NH

O

OHO

O

Anti-hypertensiveC20H28N2O5

Q.14


NH

O

O

N

O

OHO

enalapril293

Ester

Carboxyl

Tertiary amide

Secondary amino

Anti-hypertensiveC20H28N2O5

Q.14


O

O

N O

O

cocaine294

A local anestheticQ.14

sp2 hybridized

sp3 hybridized


A local anesthetic

Tertiary amino

O

O

N O

O

O

O

N O

O

cocaine

Ester

C17H21NO4

Q.14


O OHO

N

codeine296

Addictive cough medicine

Q.14

sp2 hybridized

sp3 hybridized


O OHO

N

codeine

O OHO

N

297

Addictive cough medicine

Ether

Tertiary amino

Hydroxyl

C=C bond

C18H21NO3

Q.14


O OHHO

N

morphine298

A potent addictive analgesic from opium

Q.14

sp2 hybridized

sp3 hybridized


O OHHO

N

morphine299

O OHHO

N

A potent addictive analgesic from opium

Ether

Hydroxyl Hydroxyl

Tertiary amino

C=C bond

C17H19NO3

Q.14


O OO

N

O O

heroin

Acetylated morphine

Q.14

sp2 hybridized

sp3 hybridized


O OO

N

O O

heroin

Acetylated morphine

O OO

N

O O

Tertiary amino

Ester

Ester

Ether

C=C bond

C21H23NO5

Q.14


O OHO

N

etorphine

OH

Tranquilizer for elephants – 2000 times more potent than morphine

Q.14

sp2 hybridized

sp3 hybridized


O OHO

N

etorphine

OH

O OHO

N

OH

Tranquilizer for elephants – 2000 times more potent than morphine

Hydroxyl

Hydroxyl

Ether C=C

Tertiary amino

C25H33NO4

Q.14


O

N

methadone

Narcotic analgesic

Q.14

sp2 hybridized

sp3 hybridized


O

N

methadone

Narcotic analgesic

O

NTertiary amino

Carbonyl C21H27NO

Q.14


SO

O

NN

O

N

NHO

N

N

SO

O

NN

O

N

NHO

N

N

viagra

You don’t need it !

Q.14

sp2 hybridized

sp3 hybridized


SO

O

NN

O

N

NHO

N

N

SO

O

NN

O

N

NHO

N

N

viagraEther

Tertiary amino

C=C

Secondary amide

C=N

C22H30N6O4S

Q.14


O

O

OH

O CH3

Aspirin

Analgesics and antipyretics

2-(acetyloxy)benzoic acid

1

2


OH

NH CH3

O Acetaminophen

Analgesics and antipyretics

N-(4-hydroxyphenyl)acetamide

1

4


O

O

OH

OH

OH

OH

Vitamin C

Helps maintain elasticity of the skin, aids the absorption

of iron and improves resistance to infection.

1

23

4

51

2

5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one

O

furan

O

O

furan-2(3H)-one

O

O

furan-2(5H)-one


OH

OH

OH

NH

CH3 CH3

CH3 Albuterol

Treating asthma, emphysema and chronic

bronchitis

4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

1

241

2


Camphor(樟腦 )

1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

12

345

6

7


NHCH3

O

Cl

Ketamine( 氯胺酮 )Ketamine( 氯胺酮 )

C13H16ClNO

1

2

12

313

cyclohexanone

2-(2-chlorophenyl)

2-(methylamino)

2-(2-chlorophenyl)

-2-(methylamino)


NHCH3

O

O

Cl

12

3

12

314

3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione


NHCH3

O

O

Cl

12

3

6

12

315

6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione


C24H15Cl2NO8

(2Z)-3-(acetyloxy)-2-(4-chloro-5-cyano-2-formylspiro[2.2]pent-1-yl)-3-(3'-chloro-4,6-dioxospiro[bicyclo[3.1.0]hexane-3,1'-cyclobutane]-1,3'-dien-2'-yl)prop-2-enoic prop-2-enoic anhydride

Cl

O

O

O

O

O

CH2

Cl

N

O

O

OCH3

Name it !

Date post:	18-Dec-2015
Category:	Documents
Upload:	muriel-russell
View:	393 times
Download:	31 times

New Way Chemistry for Hong Kong A-Level Book 3A 1 Nomenclature & Introduction of Major Families of...

Documents