L10 - Introduction OF Organic CHEMISTRY and Fundamental OF Polymer Chemistry Part I
L10 - Introduction OF Organic CHEMISTRY and Fundamental OF Polymer Chemistry Part I
L10 - Introduction OF Organic CHEMISTRY and Fundamental OF Polymer Chemistry Part I
L10: INTRODUCTION OF
ORGANIC CHEMISTRY AND
FUNDAMENTAL OF POLYMER
CHEMISTRY (I)
L10: PENGENALAN KIMIA ORGANIK
DAN ASAS KIMIA POLIMER (I)
International
Union of
Pure and Colloquially:
“eye-you-pack”
Applied
Chemistry
Number of
Alkane Alkyl group Alkene Alkyne
carbon atoms
1 Methane Methyl – –
2 Ethane Ethyl Ethene (ethylene) Ethyne (acetylene)
3 Propane Propyl Propene (propylene) Propyne (methylacetylene)
4 Butane Butyl Butene (butylene) Butyne
5 Pentane Pentyl Pentene Pentyne
6 Hexane Hexyl Hexene Hexyne
7 Heptane Heptyl Heptene Heptyne
8 Octane Octyl Octene Octyne
9 Nonane Nonyl Nonene Nonyne
10 Decane Decyl Decene Decyne
Types of organic formulas
CH3CH2CH3
condensed
Wedge/dash
H H
H H
skeletal
H H H H
8
Types of organic formulas
CH3
I
CH3 – CH2 – CH2 – CH2 –CH2 – CH2 – CH3
I I
CH3 CH3
10
ALKANES
Naming Alkanes : Parent
Follows specific rules;
C-C
C-C-C-C-C-C-C-C-C all possibilites
must be examined
C 9
it won’t always be
the horizontal one
try these also …….. as shown here
C-C
C- C-C-C -C-C-C-C-C C-C
C 6 C-C-C- C-C-C-C-C-C
C
8
13
ALKANES Nomenclature
Prefix-Parent-Suffix
3-ethyl-6-methyl octane 14
ALKANES Let’s do it !
CH2 CH3
CH3CH2CH2CH CH3
CH3
CH2
H3C CH CH CH2CH3
CH2CH2CH3
15
ALKANES
• If two different chains of equal length are present,
choose the one with the larger number of branch
points.
CH3
CH3CHCHCH2CH2CH3
CH2 CH3
16
ALKANES
• If branching is equal distant away from both ends
of the parent chain, begin at the end nearer the
second branch point.
17
ALKANES
• Identify the number of substituent:
– Assign a number to each substituent according
to its point of attachment to the main chain.
9 8
H3C CH2 CH3 3-ethyl
3
CHCH2CH2CHCHCH2CH3 4-methyl
CH33-ethyl-4,7-dimethylnonane
7-methyl
7 6 5 4 CH2 CH3
2 1
18
ALKANES
• If there are two substituent on the same carbon,
assign them both the same number.
4-ethyl-2,4-dimethylhexane
CH3 CH3
CH3CH2CCH2CHCH3 2-methyl
4-methyl
CH2 CH3 4-ethyl
19
ALKANES
CH 2 CH 3
3-methylhexane
CH 3 CH 2 CH 2 CH CH 3
CH3
4-ethyl-3-methylheptane
CH2
CH3CHCHCH2CH3
CH2 CH2 CH3
20
ALKANES
CH3
CH3CHCHCH 2CH2CH3
CH 2 CH 3
3-ethyl-2-methylhexane
21
ALKANES Alkyl group as substituent group
The alkyl group is derived from the alkane groups by reducing
Alkyl groups can also be branched. For example,
one hydrogen atom. The general formula for alkyl group is
there are three constitutional isomers of the
CnH2n+1 . The letter R is used to represent the alkyl group.
butyl substituent.
The names of the substituents formed by the removal of one
hydrogen from the end of the chain is obtained by changing
the suffix -ane to -yl. CH3 CH CH3
Number of
carbon atoms
Alkyl group isopropyl
1 Methyl • CH3CH2CH2-, n-propyl
2 Ethyl
5 Pentyl CH3
6 Hexyl
7 Heptyl
CH3 CH CH2 CH3 CH3 CH3 CH CH2
8 Octyl sec-butyl H3C C CH3 isobutyl
9 Nonyl
10 Decyl
tert-butyl
22
ALKANES
H3C CH CH3
H 3C CH2 CH2 CH CH2 CH2CH3
4-isopropylheptane
23
ALKANES If you can name this, you can name
anything!
2,6,6-trimethyl
CH3 CH3
CH3 CH CH2
4-isopropyl
4-isopropyl-2,6,6-trimethylnonane 24
ALKANES Isomerism
• All the alkanes with 4 or more carbon atoms in them show structural
isomerism.
• This means that there are two or more different structural formulae that
you can draw for each molecular formula.
• For example, C4H10 could be either of these two different molecules:
2-cyclobutyl-5-methylhexane
not
(1,4-dimethylpentyl)cyclobutane
27
ALKENES
Number of Name Molecular Formula
carbon
atoms
• Alkenes are also called olefins, which contain
1 - -
C=C double bonds. 2 Ethene C2H4
• The general formula for an alkene is CnH2n, 3 Propene C3H6
4 Butene C4H8
where n is the number 1, 2, 3…. 5 Pentene C5H10
• Terminal alkenes have the double bond at the 6 Hexene C6H12
end of the carbon chain. 7 Heptene C7H14
8 Octene C8H16
• Internal alkenes have at least one carbon atom 9 Nonene C9H18
bonded to each end of the double bond. 10 Decene C10H20
29
ALKENES
Naming an alkene in
which the longest
carbon chain does not
contain both atoms of
the double bond
Examples of
cycloalkene
nomenclature
30
ALKENES
•Rings have “cyclo” prefix - the double bond must be numbered 1,2
ALKENES IUPAC Nomenclature
CH3
CH3 5 4 3 2 1
6 5 4 3 2 1
CH3 CH2 CHC=CH 2
CH3 CH2 CHCH2 CH=CH 2
CH2 CH3
4-Methyl-1-hexene 2-Ethyl-3-methyl-1-pentene .
2
4 1 CH3
5
3 CH3 3
4
6 CH3
1 2 5
3-Methylcyclo- 1,6-Dimethylcyclo-
pentene hexene
32
ALKENES Nomenclature : Name this!
CH3
CH3CHCH CHCH2CH3
CH3
Nomenclature : THE ANSWERS
ALKENES
CH3
CH3CHCH CHCH2CH3
2-methyl-3-hexene 2-methyl-1,3-butadiene
CH3
1-methylcyclohexene 1,4-cyclohexadiene
1-ethyl-1,4-cyclohexadiene 2-methyl-1,3-Butadiene
ALKENES Common Names
35
ALKENESNomenclature : Name this!
H3C CH
3
CH3
H2C CHCHCCH3
CH2 CHCH2CH2C CH2
CH3
CH3 CH CH
2 3
CH3
CH3CC CHCH2CH2CH3
CH3CH2CH CCH2CH3 CH3
36
ALKENES
Nomenclature : THE ANSWERS
H3C CH
3
CH3
H2C CHCHCCH3
CH2 CHCH2CH2C CH2
CH3
3,4,4-trimethyl-1-pentene 2-methyl-1,5-hexadiene
CH3 CH CH
2 3
CH3
CH3CC CHCH2CH2CH3
CH3CH2CH CCH2CH3 CH3
3-ethyl-2,2-dimethyl-3-heptene
3-methyl-3-hexene
37
ALKYNES
Number of Name of Molecular Formula
carbon atoms alkyne
1 - -
• Alkynes contain a triple bond.
2 Ethyne C2H2
• General formula is CnH2n-2. 3 Propyne C3H4
• Two elements of unsaturation for each 4 Butyne C4H6
triple bond. 5 Pentyne C5H8
• The simplest possible alkyne is the two 6 Hexyne C6H10
carbon triple bond, which would be called 7 Heptyne C7H12
ethyne. 8 Octyne C8H14
9 Nonyne C9H16
10 Decyne C10H18
38
ALKYNES Nomenclature: IUPAC
• Find the longest chain containing the triple bond. Assigning priority
• Change -ane ending to -yne. • Alkenes and alkynes are considered to
have equal priority.
• Number the chain, starting at the end closest to • In a molecule with both a double and a
triple bond, whichever is closer to the end
the triple bond. of the chain determines the direction of
• Assigning priority numbering.
• In the case where each would have the
• Give branches or other substituent a number to same position number, the double bond
takes the lower number.
locate their position. • In the name, “ene” comes before “yne”
because of alphabetization.
39
ALKYNES
Multiple Double/Triple Bonds
ALKYNES Name these:
CH3 CH3
CH3 CH CH2 C C CH CH3
41
ALKYNESName these: THE ANSWERS
CH3 C CH CH3 C C CH2 CH2 Br
Propyne 5-bromo-2-pentyne
Prop-1-yne 5-bromopent-2-yne
CH3 CH3
CH3 CH CH2 C C CH CH3
2-pentyne 2,6-dimethyl-3-heptyne
Pent-2-yne 2,6-dimethylpept-3-yne
5-methyl-2-hexyne
1-hexene-4-yne
5-methylhex-2-yne
42
ALKYNES Additional Functional Groups
• All other functional groups, except ethers and halides
have a higher priority than alkynes.
The priority numbering system determines that the group -COOH
Priority
with the highest priority will receive a very small number.
increases -CHO
CH3 -C=O
-OH
CH2 CH CH2 CH C CH
NR2
4-methyl-1-hexen-5-yne
4-methylhex-1-en-5-yne -C≡C-
OH -C=C
4-hexyn-2-ol
hex-4-yn-2-ol
43
ALKYL HALIDES
• Alkyl halide is an organic compound containing at least
one carbon-halogen bond (C-X)
• The halogens are series of nonmetal elements from
Group 17 IUPAC Style (formerly: VII, VIIA) of the
periodic table, comprising fluorine(F), chlorine(Cl),
bromine(Br), iodine(I), and astatine(At).
• X (F, Cl, Br, I) replaces H.
• Can contain many C-X bonds.
ALKYL HALIDES
• Alkyl halides are formally derived from alkanes by exchanging
hydrogen for halogen (fluorine, chlorine, bromine, and iodine).
• Depending on the degree of substitution at the carbon atom carrying
the halogen, alkyl halides are classified into primary, secondary and
tertiary alkyl halides.
46
ALKYL HALIDES
Naming with Multiple Halides
• If more than one of the same kind of halogen is present,
use prefix di, tri, tetra.
• If there are several different halogens, number them and
list them in alphabetical order.
47
ALKYL HALIDES
• If different halogens are present, number each according to
its position on the chain, but list substituents alphabetically.
Cl Cl
CH3CHCCHCH2CH3
BrCH3
3-bromo-2,3-dichloro-4-methylhexane
48
ALKYL HALIDES
Br
Cl Br
Br
2-bromo-6-chloroheptane 1,5-dibromo-2-methylhexane
49
ALCOHOLS
• An alcohol is an organic compound with a hydroxyl (OH) functional group on an
aliphatic carbon atom.
• Because OH is the functional group of all alcohols, we often represent alcohols by
the general formula ROH, where R is an alkyl group.
• Alcohols are common in nature.
• Most people are familiar with ethyl alcohol (ethanol), the active ingredient in
alcoholic beverages, but this compound is only one of a family of organic
compounds known as alcohols.
ALCOHOLS
• Alcohols contain an OH group connected to a saturated C (sp3)
• They are important solvents and synthesis intermediates
• Phenols contain an OH group connected to a carbon in a benzene ring
• Methanol, CH3OH, called methyl alcohol, is a common solvent, a fuel
additive, produced in large quantities
• Phenol, C6H5OH (“phenyl alcohol”) has diverse uses - it gives its name
to the general class of compounds
• OH groups bonded to vinylic, sp2-hybridized carbons are called enols
51
ALCOHOLS
Naming Alcohols
• General classifications of alcohols based on substitution on C to which OH is
attached
• Methyl (C has 3 H’s), Primary (1°) (C has two H’s, one R), secondary (2°) (C
has one H, two R’s), tertiary (3°) (C has no H, 3 R’s),
52
ALCOHOLS
IUPAC Rules for Naming Alcohols
• Select the longest carbon chain containing the hydroxyl group, and derive
the parent name by replacing the -e ending of the corresponding alkane
with -ol . The chain is numbered from the end nearest the OH group.
• The number that indicates the position of the OH group is prefixed to the
name of the parent hydrocarbon, and the -e ending of the parent alkane
is replaced by the suffix -ol. (In cyclic alcohols, the carbon atom bearing
the OH group is designated C1, but the 1 is not used in the name.)
Substituents are named and numbered as in alkanes.
53
ALCOHOLS
IUPAC Rules for Naming Alcohols cont.
• If more than one OH group appears in the same molecule (polyhydroxy alcohols), suffixes such as -
diol and -triol are used. In these cases, the -e ending of the parent alkane is retained.
54
ALCOHOLS Give the IUPAC name for this compound
1. Ten carbon atoms in the LCC makes the compound a derivative of decane, and
the OH on the third carbon atom makes it a 3-decanol.
2. The carbon atoms are numbered from the end closest to the OH group. That
fixes the two methyl (CH3) groups at the sixth and eighth positions. The name
is 6,8-dimethyl-3-decanol (not 3,5-dimethyl-8-decanol).
55
ALCOHOLS
Give the IUPAC name for this compound
HOCH2CH2CH2CH2CH2OH
56
CARBONYL
• A carbonyl group consists of
carbon and oxygen joined
together by a double bond.
• The joining of carbonyl carbon is
with hydrogen on one side in
aldehydes
• The joining of two carbon atoms
on both the side of carbonyl
carbon in the case of ketones.
CARBONYL
Naming aldehydes & ketone
GROUP
• The IUPAC naming of aliphatic aldehydes and aliphatic ketones is comparatively
easy.
• It is derived by taking the corresponding alkane and replacing the end letter –e of
the alkane with either –al or –one. In case of aldehyde –al is written whereas in case
of ketone –one is written.
• The numbering of the longest carbon chain in the case of aldehyde begins from the
carbon-containing the aldehyde group. However, in case of ketones, the numbering
starts from the side of carbon-containing the carbonyl group.
CARBONYL
GROUP Naming aldehydes & ketone
• Adding prefix in alphabetical order along with the numerals help in indicating the
positions of the substituents in the carbon chain. This is same for cyclic ketones as
well. In the case of cyclic ketones, the numbering begins with the carbonyl carbon.
• We have to add the suffix carbaldehyde after the complete name of the
cycloalkane in case the attachment is between an aldehyde group and a ring. The
numbering of the ring begins from the carbon atom that is attached to the
aldehyde group.
• First of all, a ketone carbonyl function may be located anywhere (chain or ring). Its
position is usually given by a location number (2, 3, 4,...).
• Chain numbering normally starts from the end nearest the carbonyl group. For
example, very simple ketones (see picture) do not require a locator number, since
there is only one possible site for a ketone carbonyl function.
• The names for ketones are formed by naming both alkyl groups attached to the
carbonyl then adding the suffix -one. Very important rule is that the attached alkyl
groups are arranged in the name alphabetically
CARBONYL
Carboxylic Acid
GROUP
• The functional group of a carboxylic acid is a carboxyl group.
O O
C COOH CO2 H
O H O H
Alternative representations for a carboxyl group
• The general formula for an aliphatic carboxylic acid is RCOOH; that for an aromatic carboxylic acid is
ArCOOH.
CARBONYL
Nomenclature - IUPAC
GROUP
• IUPAC names: drop the -e from the parent alkane and add the suffix -oic acid.
O
HCOOH CH3 COOH OH
Methanoic acid Ethanoic acid 3-Methylbutanoic acid
(Formic acid) (Acetic acid) (Isovaleric acid)
CARBONYL
Nomenclature - IUPAC
GROUP
• The carboxyl group takes precedence over most other functional groups.
OH O O O O
H2 N
OH OH OH
(R)-5-Hydroxyhexanoic 5-Oxohexanoic acid 4-Aminobutanoic acid
acid
CARBONYL
Nomenclature - IUPAC
GROUP
• Dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing both carboxyl
groups.
O
O O
HO
OH
HO OH
O
Ethanedioic acid Propanedioic acid
(Oxalic acid) (Malonic acid)
O O O O
HO HO
OH HO OH OH
O O
Butanedioic acid Pentanedioic acid Hexanedioic acid
(Succinic acid) (Glutaric acid) (Adipic acid)
CARBONYL
Nomenclature - IUPAC
GROUP • If the carboxyl group is bonded to a ring, name the ring compound and add
the suffix -carboxylic acid.
2
1 COOH
3
HOOC COOH
2-Cyclohexenecarboxylic trans-1,3-Cyclopentanedicarboxylic
acid acid
COOH
Benzoic 2-Hydroxybenzoic 1,2-Benzenedicarboxylic 1,4-Benzenedicarboxylic
acid acid acid acid
(Salicylic acid) (Phthalic acid) (Terephthalic acid)
AROMATICS
• Aromatic compounds are ring structures with
unusual stability due to delocalized pi electron
density that is shared between all of the carbon
atoms in the ring.
• The most common aromatic compounds contain
benzene ring, a ring of six carbon atoms each
holding one H or one another atom or group.
• The benzene ring is represented as a hexagon
either with alternating single and double bonds
or with a circle.
66
AROMATICS Naming aromatics
In the International Union of Pure and Applied Chemistry (IUPAC) system, aromatic hydrocarbons are
named as derivatives of benzene.
Aromatic Compounds with a Single Substituent
1. When there is a single substituent on a benzene 3. If the substituent contains more than six
ring and the substituent contains six or fewer carbons, the alkane portion is named first,
carbons, the substituent is included as a prefix to and a benzene ring is substituent, the term
benzene. ( C6H5CH2-) phenyl is used ( C6H5-) (the aromatic ring
2. Alkyl groups are named according to the alkane portion is added as a suffix) . For instance, an
series convention ending with -yl: methyl (for a aromatic ring bonded to an 8-carbon chain
single carbon), ethyl (for two carbons), propyl (for would be 1-phenyloctane, and not
three carbons), etc. octylbenzene.
67
AROMATICS Naming aromatics
Aromatic Compounds with two substituents
68
AROMATICS Naming aromatics
Aromatic Compounds with multiple substituents
• When there are more than two substituents on • When there are more than two different
the benzene ring, their positions are shown by substituents, the substituents are written
numbers. according to their alphabetical order.
• The ring carbon atoms are given numbers in such
a way that the substituents are at the lowest
4- Bromo -1,2 – dimethylbenzene
position possible.
Cl
Br
Cl • Whenever a substituent can give a new parent name with
the benzene ring, the carbon atom that carries the
Br Br substituent is now recognised as at position 1.
Cl
√ 1,2,3 – trichlorobenzene √ 1,2,4 – tribromobenzene
X1,2,6 - trichlorobenzene 2,5 – dimethylphenol
X 1,3,4 – tribromobenzene
69
AMINES
Amines contain the amino (NR1R2R3) group, a Amines are classified as primary (1◦), secondary (2◦) or
nitrogen attached to an alkyl group. Common tertiary (3◦) depending on the number of alkyl or aryl
names of amines are formed from the names of groups bonded to the nitrogen atom of the molecules.
the alkyl groups bonded to nitrogen, followed
by the suffix – amine.
The prefixes di, - tri-, and tetra- are used to
describe two, three, or four identical
substituents.
70
AMINES Naming the Amines
butan-2-amine or 2-butylamine
(or sec-butylamine)
71
AMINES Naming the Amines
N
Secondary amines
H
1. Secondary amines have two alkyl groups attached to
the N. Functional group is an amine, therefore
2. The root name is based on the longest chain with the - suffix = -amine
NH attached. Hydrocarbon structure is an alkane
3. The chain is numbered so as to give the amine unit the therefore -ane
lowest possible number. The longest continuous chain is C2
4. The other alkyl group is treated as a substituent, with therefore root = eth
N as the locant.
5. The N locant is listed before numerical locants, e.g. N-methylethylamine
N,2-dimethyl.... or
6. The amine suffix is appended to the appropriate alkyl N-methylethanamine
root or alkana- root.
72
AMINES Naming the Amines
N
Tertiary amines
1. Tertiary amines have three alkyl group attached to the N. Functional group is an amine, therefore
2. The root name is based on the longest chain with the -N suffix = -amine
attached. Hydrocarbon structure is an alkane
3. The chain is numbered so as to give the amine unit the therefore -ane
lowest possible number. The longest continuous chain is C1
4. The other alkyl groups are treated as substituents, with N as therefore root = meth
the locant.
5. The N locant is listed before numerical locants, e.g. N,2-
Name : N,N-dimethylmethylamine
dimethyl.... or
6. The amine suffix is appended to the appropriate alkyl root trimethylamine
or alkana- root.
73
END OF PART I