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Chapter 4

Alkanes: Nomenclature,
Conformational Analysis, and an
Introduction to Synthesis

NAMA : AMELIA AYNUL PUTRI


NIM : 1813031031
KELAS : 1B
t Shapes of Alkanes
g"Straight-chain" alkanes have a zig-zag orientation when they are
in their most straight orientation
H Straight chain alkanes are also called unbranched alkanes

Propane
CH3CH2CH3 or

Butane
CH3CH2CH2CH3 or

Pentane

CH3CH2CH2CH2CH3 or

Chapter 4 2
gBranched alkanes have at least one carbon which is attached to
more than two other carbons

Isobutane
CH3 CH CH3

CH3

Isopentane

CH3 CH CH2 CH3


CH3

Neopentane
CH3

CH3 C CH3

CH3

Chapter 4 3
gConstitutional isomers have different physical properties (melting
point, boiling point, densities etc.)
H Constitutional isomers have the same molecular formula but differentconnectivity
of atoms

bp ( o C)o Destinityb Index of Refraction c


Molecular Sructural mp
Formula Formula (o C) (g mL -1 ) (nD 20o C)
(1atm)
C6H14 CH3CH2CH2CH2CH2CH3 -95 20
68.7 0.6594 1.3748
C6H14 CH3CHCH2CH2CH3 -153.7
20
60.3 0.6532 1.3714
CH3

C6H14 CH3CH2CHCH2CH3 20
-118 63.3 0.6643 1.3765
CH3

C6H14 CH3CH CHCH3 -128.8 20


58 0.6616 1.3750
CH3 CH3

CH3

C6H14 CH3 C CH2CH3 -98 49.7 0.6492


20
1.3688

CH3

a
Unless otherwise indicated, all boiling points given in this book are at 1 atm or 760 torr.
b
The superscript indicates the temperature at which the density was measured
c
The index of refraction is a measure of the ability of the alkane to bend (refract) light rays. The values reported are
for light of teh D line of the sodium spectrum ( nD )
Chapter 4 4
gThe number of constitutional isomers possible for a given
molecular formula increases rapidly with the number of carbons

Possible Number of
Molecular Formula Constitutional Isomers

C4H10 2
C5H12 3
C6H14 5
C7H16 9
C8H18 18
C9H20 35
C10H22 75
C15H32 4,347
C20H42 366,319
C30H62 4,111,846,763
C40H82 62,481,801,147,341

Chapter 4 5
t IUPAC Nomenclature of Alkanes, Alkyl Halides
and Alcohols
gBefore the end of the 19th century compounds were named using
nonsystematic nomenclature
gThese "common" or "trivial" names were often based on the
source of the compound or a physical property
gThe International Union of Pure and Applied Chemistry (IUPAC)
started devising a systematic approach to nomenclature in 1892
gThe fundamental principle in devising the system was that each
different compound should have a unique unambiguous name
gThe basis for all IUPAC nomenclature is the set of rules used for
naming alkanes

Chapter 4 6
l Nomenclature of Unbranched Alkanes
Number of Number of
Carbon Carbon
Atoms Structure Name Atoms Structure

1 CH4 Heptadecane 17 CH3(CH2)15CH3

2 CH3CH3 Octadecane 18 CH3(CH2)16CH3

3 CH3CH2CH3 Nonadecane 19 CH3(CH2)17CH3

4 CH3(CH2)2CH3 Eicosane 20 CH3(CH2)18CH3

5
CH3(CH2)3CH3 Heneicosane 21 CH3(CH2)19CH3

CH3(CH2)4CH3 Docosane 22 CH3(CH2)20CH3


6
CH3(CH2)5CH3 Tricosane 23 CH3(CH2)21CH3
7
CH3(CH2)6CH3 Triacontane 30 CH3(CH2)28CH3
8
CH3(CH2)7CH3 Hentriacontane 31 CH3(CH2)29CH3
9
CH3(CH2)8CH3 Tetracontane 40 CH3(CH2)38CH3
10
CH3(CH2)9CH3 Pentacontane 50 CH3(CH2)48CH3
11
CH3(CH2)10CH3 Hexacontane 60 CH3(CH2)58CH3
12
CH3(CH2)11CH3 Heptacontane 70 CH3(CH2)68CH3
13
CH3(CH2)12CH3 Octacontane 80 CH3(CH2)78CH3
14 Nonacontane 90
CH3(CH2)13CH3 CH3(CH2)88CH3
15 CH3(CH2)14CH3 Hectane 100 CH3(CH2)98CH3

Chapter 4 7
l Nomenclature of Unbranched Alkyl groups
gThe unbranched alkyl groups are obtained by removing one
hydrogen from the alkane and named by replacing the -ane of the
corresponding alkane with -yl

ALKANE ALKYL GROUP ABBREVIATION


CH3 H CH3 Me
becomes
Methane Methyl

CH3 CH2 Et
CH3CH2 H
becomes

Ethane Ethyl

CH3CH2 CH2 H becomes CH 3CH 2CH 2 Pr

Propane Propyl

CH3CH2CH2CH2 H becomes CH3CH2CH2CH2 Bu

Butane Butyl

Chapter 4 8
l Nomenclature of Branched-Chain Alkanes (IUPAC)
gLocate the longest continuous chain of carbons; this is the parent
chain and determines the parent name.

CH3CH2CH2CH2 CHCH3
CH2
CH3

gNumber the longest chain beginning with the end


of the chain nearer the substituent
gDesignate the location of the substituent

6 5 4 3 2 1
7 6 5 4 3
CH3CH2CH2CH2 CHCH3
CH3CH2CH2CH2 CHCH3
2 CH
CH3 2
1 CH3

2- Methylhexane 3-Methylheptane

gWhen two or more substituents are present, give each substituent


a number corresponding to its location on the longest chain
HSubstituents are listed alphabetically

Chapter 4 9
gWhen two or more substituents are identical, use the prefixesdi-,
tri-, tetra- etc.
HCommas are used to separate numbers from each other
HThe prefixes are used in alphabetical prioritization
gWhen two chains of equal length compete to be parent, choose
the chain with the greatest number of substituents
7 6 5 4 1
3 2
H3C CH2 CH CH CH CH CH3

CH3 CH3 CH3

CH2

CH3

2,3,5-Trimethyl-4-propylheptane
(four substituents)

gWhen branching first occurs at an equal distance from either end


of the parent chain, choose the name that gives the lower number
at the first point of difference

Chapter 4 10
l Nomenclature of Branched Alkyl Chains
gTwo alkyl groups can be derived from propane

Three-Carbon Groups
CH 3 CH 2CH 2
Propylgroup
CH3CH2CH3
Propane
CH3 CH

CH3
1- Methylethyl or isopropyl group

gFour groups can be derived from the butane isomers


Four-Carbon Groups CH3CH2 CH2
Butyl group
CH3CH2CH2CH3
Butane
H3C CH2 CH

CH3
1-Methylpropil or sec-butyl group
CH3 CH CH2

CH3
H3C CHCH3 2-Methylpropil or isobutyl group
CH3
CH3
CH3C
Isobutane CH3
1,1-Dimethylethyl or tert-butyl group

Chapter 4 11
gThe neopentyl group is a common branched alkyl group
CH3

H 3C C CH2

CH3
2,2-Dimethylpropyl or neopentyl group

gExamples
CH3CH2 CH2 CH CH2CH2 CH3

CH3 CH

CH3
4-(1-Methylethyl)heptane or 4-isopropylheptane

CH3 CH2 CH2 CH CH2 CH2 CH2 CH3

CH3 C CH3

CH3

4-(1,1-Dimethyethyl)octane or 4-tert-butyloctane

Chapter 4 12
t Classification of Hydrogen Atoms
gHydrogens take their classification from the carbon they are
attached to

1o Hydrogens atoms

CH3

CH3 CH CH2 CH3


3o hydrogen atom
20Hydrogen atoms

Chapter 4 13
l Nomenclature of Alkyl Halides
gIn IUPAC nomenclature halides are named as substituents on the
parent chain
CH3 CH3

CH3 CHCH2 CHCH3


H3C CHCH CH2 CH3
Cl
Cl

2-Chloro-3-methylpentane 2-Chloro-4-methylpentane

gIn common nomenclature the simple haloalkanes are named as


alkyl halides
HCommon nomenclature of simple alkyl halides is accepted by IUPAC and still used

(CH3)3C Br CH3CH CH2 Cl CH3


CH3 CH2 Cl CH3 CH CH3
CH3 CH3C CH2 Br
Br
CH3

tert-Butyl Isobutyl Neopentyl


Ethyl Isopropyl bromide chloride bromide
chloride bromide

Chapter 4 14
l IUPAC Substitutive Nomenclature
gAn IUPAC name may have up to 4 features: locants, prefixes,
parent compound and suffixes
gNumbering generally starts from the end of the chain which is
closest to the group named in the suffix

CH3 CH2CH CH2 CH2 CH2 OH

CH3

4-Methly-1-hexanol

Locant Prefix Locant Parent Suffik

l IUPAC Nomenclature of Alcohols


gSelect the longest chain containing the hydroxyl and change the
suffix name of the corresponding parent alkane from -ane to -ol
gNumber the parent to give the hydroxyl the lowest possible
number
gThe other substituents take their locations accordingly

Chapter 4 15
gExamples
CH3
3 2 1 1 2 3 4 5
Cl CH 2 CH2 CH 2 OH H 3C CH CH2 C CH3

OH CH3
3-Chloro-1-propanol 4,4-Dimenthyl-2-pentanol
or 3-Chloropropan-1-ol or 4,4-dimenthyipentana-2-ol

gCommon Names of simple alcohols are still often used and are
approved by IUPAC
H3C CH2CH2OH H3C CH2 CH2 CH2OH H3C CH2 CH CH3

OH
Propyl alcohol Butyl alcohol

CH3 CH3 CH3

H3C COH H3C HC CH2OH H3C C CH2 CH3

CH3 CH3

Isobutyl alcohol Neopentyl alcohol

Chapter 4 16
gAlcohols with two hydroxyls are called diols in IUPAC nomenclature and glycols in
common nomenclature

CH2 CH2 H3C HC CH2 H2CCH2CH2


OH OH OH OH OH OH
Common Etgylene glicol Propylene glycol Trimethylene glycol
Substitutive 1,2-Ethanediol or ethane-1,2-diol 1,2-propanediol 1,3-propanediol
or propane -1,2-diol or propane-1,3-diol

Chapter 4 17
t Nomenclature of Cycloalkanes
lThe prefix cyclo- is added to the name of the alkane with
the same number of carbons
gWhen one substituent is present it is assumed to be at position
one and is not numbered
gWhen two alkyl substituents are present the one with alphabetical
priority is given position 1
gNumbering continues to give the other substituent the lowest
number
gHydroxyl has higher priority than alkyl and is given position 1
gIf a long chain is attached to a ring with fewer carbons, the
cycloalkane is considered the substituent

Chapter 4 18
CH3
CH 2CH 3
CH 3CHCH 3 CH3 1
2

3
4

CH2CH3 Cl
Isopropylcyclohexane 1-Ethyl-3-methylcyclohexane 4-Chloro-2-ethyl-1-methylcyclohexane
(not 1-ethyl-5-methylcyclohexane) (not 1-chloro-3-ethyl-4-methylcyclohexane

CH3
Cl
CH3

Chlorocyclopentane 2-Methylcyclohexanol

CH 2CH 2CH 2CH 2CH 3

1-Cyclobuthylpentane
1,3-Dicyclohexylpropane

Chapter 4 19
t Bicyclic compounds
gBicyloalkanes contain 2 fused or bridged rings
gThe alkane with the same number of total carbons is used as the
parent and the prefix bicyclo- is used

One-carbon
Bridgehead
bridge
CH
CH2 CH2
Two-carbon Two-carbon
CH2
bridge bridge =
CH2 CH2
CH
Bridgehead

A bicycloheptane

gThe number of carbons in each bridge is included in the middle of


the name in square brackets

7 1 3
8
CH3 3 H3C 8

6 4
6 7
5 4 5

8-Methylbicyclo[3.2.1]octane 8-Methylbicyclo[4.3.0]nonane

Chapter 4 20

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