2-Chem 109 Aliphatic Hydrocarbons Modified 1

Fundamentals of Organic Chemistry
CHEM 109
For Students of Health Colleges
Credit hrs.: (2+1)
King Saud University
College of Science, Chemistry Department
CHEM 109 CHAPTER 2. ALIPHATIC HYDROCARBON

Learning Objectives
2
At the end of this chapter, students will able to:

 Identify the different types of aliphatic hydrocarbons (alkanes, cycloalkanes, alkenes,
cycloalkenes and alkynes).
 Recognize the basic properties (structure, physical and chemical properties) of alkanes,
alkenes and alkynes.
 Identify the structure of a hydrocarbon from its IUPAC and common name.
 Identify the name from the structure of hydrocarbons
 Explain the type of isomer in organic compounds and draw the different isomer structures
of the compound.
 Know the different methods for the synthesis of aliphatic hydrocarbons.
 Identify the general reactions of aliphatic hydrocarbons.
Hydrocarbons
3
o Hydrocarbons are Organic Compounds, which contain only the two elements
carbon and hydrogen.
o Aliphatic hydrocarbons are subdivided into:
 Saturated hydrocarbons
 Alkanes; CnH2n+2 (contain carbon-carbon single bond)
 Cycloalkanes: CnH2n (contain carbon-carbon single bond in a single ring)
Alkanes and cycloalkanes are so similar that many of their properties can be
considered side by side.
 Unsaturated
hydrocarbons
 Alkenes : C H (contain carbon-carbon double bond)
n 2n
 Alkynes : Cn H2n-2 (contain carbon-carbon triple bond)

Hydrocarbons
4
Hydrocarbons
Aromatic Aliphatic
Unsaturated
Cyclic
Saturated Unsaturated
Alkanes Alkenes
Alkynes
(Paraffin's) (Olefins)
(Acetylenes)
CnH2n+2 and CnH2n CnH2n and CnH2n-2
Single ring Fused ring Conjoined
CnH2n-2
benzene
ring
CH4
H 2C CH2 HC CH
H 3C CH3 H3C C CH2
H 3C C CH
CH3
Saturated Hydrocarbons
1. Alkanes
5
o General formula is CnH2n+2 Names, Molecular formulas and Number of Isomers of the
first ten Alkanes
o In alkanes, the four sp3
orbitals of carbon repel each
other into a tetrahedral
arrangement with bond
angles of 109.5º like in CH4.
o Each sp3 orbital in carbon
overlaps with the 1s orbital
of a hydrogen atom to form a
C-H bond.
Classes of Carbons and 1. Alkanes
6
Hydrogen
o A primary (1) carbon is one that is bonded to only one other carbon.
o A secondary (2) carbon is one that is bonded to two other carbons.
o A tertiary (3) carbon is one that is bonded to three other carbons.
1o Hydrogen atoms
CH3
H 3C CH CH2 CH3
3o Hydrogen atom 2o Hydrogen atoms
o Hydrogens are also referred to as 1, 2, or 3 according to the type of carbon they
are bonded to.
Alkyl Group Nomenclature
7
o An alkyl group is formed by loss of a hydrogen atom from the corresponding alkane.
o General formula CnH2n+1.
o The letter R is used as a general symbol for an alkyl group.
o An alkyl group is named by replacing the suffix –ane of the parent alkane by –yl.
i.e. Alkane – ane + yl = Alkyl
8
o Examples:
 Derived from methane by removing one of the hydrogens, a one-carbon
substituent is called a methyl group.
 Thus the two-carbon alkyl group is called the ethyl group, from ethane.
9
 When we come to propane, there are two possible alkyl groups, depending on
which type of hydrogen is removed.
• If a terminal hydrogen is removed, the group is called a propyl group.
• If a hydrogen is removed from the central carbon atom, we get a different isomeric
propyl group, called the isopropyl group.
10
 For four-carbon alkyl group, there are four different butyl groups.
• The butyl and sec-butyl groups are based on n-butane.
• The isobutyl and tert-butyl groups come from isobutane.
n-butane
Nomenclature; IUPAC 1. Alkanes
11
Rules
o The older unsystematic names, (Common names).
o The IUPAC names.
International Union of Pure & Applied Chemistry
The IUPAC Rules
1) Select the parent structure; the longest continuous chain
not
Ethylhexane X
Propylpentane
The longest continuous chain is not necessarily straight.

12
Rules
2) Number the carbons in the parent chain
starting from the end which gives the lowest number for the
substituent
1 2 3 6 5 4
H2 H H2 H2 H H2
H3C C C C CH3 H3C C C C CH3
4 CH2 not 3 CH2
5 CH2 2 CH2
6 CH3 1 CH3
3-Ethylhexane
X
4-Ethylhexane
13
Rules
2) Number the carbons in the parent chain
Substituent
7 6 5 4 3 6 5 4 3 2 1
CH 3CH 2CH2CH2CHCH 3 CH 3CH 2CH2CH2CHCH 3
2 CH 2 CH3 Substituent
1 CH 3
3-Methylheptane
2-Methylhexane
To name the compound;
1) Determine The position of the substituent on the parent carbon chain by
a number.
2) The number is followed by a hyphen (-)
3) The combined name of the substituent (ethyl).
4) The parent carbon chain (hexane), So the
full name will be: 3 - Ethyl hexane
14
Rules
3) If the same alkyl substituent occurs more than once on the parent carbon chain,
the prefixes di-, tri-, tetra-, penta-, and so on
are used to indicate two, three, four, five, and so on.
5 4 3 2 1
2,2,4- Trimethylpentane
CH3 CH3
CH3
CH3CH CHCH3 CH3CCHCCH3
CH3CHCHCHCH3
CH3 CH3
CH3 CH3 CH3 CH3
2,3-Dimethylbutane 2,3,4-Trimethylpentane 2,2,4,4-Tetramethylpentane
15
Rules
4) If different alkyl substituents are attached on the parent carbon chain, they are
named in order of alphabetical order.
8 7 6 5 4 3 2 1
3,3- di ethyl
4-methyl
5- propyl
3,3-Diethyl - 4- methyl- 5 - propyl octane
Note that
CH3CH CH2 CHCH2CH3
• Each substituent is given a number corresponding to
CH3 CH2
its location on the longest chain.
• The substituent groups are listed alphabetically. CH3
4-Ethyl-2-methylhexane
16
Rules
5) When two substituent are present on the same carbon, use the number twice.
CH3
CH3CH C CHCH2CH3
CH2
CH3
3-Ethyl-3-methylhexane
6) When two chains of equal length compete for selection as the parent chain,
choose the chain with the greater number of substituents.
7 6 5 4 3 2 1
CH 3CH2 CH CH CH CH CH 3
CH 3 CH2 CH 3 CH3
CH2
CH3
2,3,5-Trimethyl-4-n-propylheptane
17
Rules
7) If substituents other than alky groups are also presents on the parent carbon
chain; all substituents are named alphabetically.
-F fluoro -NO2 nitro
-Cl chloro -NH2 amino
-Br bromo -CN cyano
-I iodo
Br
5 4H 3 2H 1
H3C C C C CH3 2- chloro
CH H 3 Cl 3-bromo
4- methyl
3-bromo -2- chloro - 4-methylpentane
Rules
Examples
18
Nomenclature of Cycloalkanes 1. Alkanes
o Cycloalkanes are saturated hydrocarbons that have at least one ring of carbon atoms.
o Cycloalkanes are named by placing the prefix cyclo- before the alkane name that corresponds
to the number of carbon atoms in the ring.
o If only one substituent is present, no number is needed to locate it.

o If there are several substituents, numbers are required.
With different substituents, the one with highest alphabetic priority is located at carbon 1.
19
Nomenclature of Cycloalkanes 1. Alkanes
o If there are more than two substituents on the ring, they are cited in alphabetical order.
o The substituent given the number 1 position is the one that results in a second substituent
getting as low a number as possible.
o If two substituents have the same low number, the ring is numbered in the direction that gives
the third substituent the lowest possible number.
o Examples,
20
Aliphatic Hydrocarbons
Physical Properties of Alkanes, Alkenes and
21
Alkynes
Those properties that can be observed without the compound undergoing a chemical
reaction such as its physical states, density, color, Boiling and melting points and solubility.
A. Physical States
C1 (C2) to C4 are gases,
C5 to C17 are liquids,
C18 and larger alkanes are wax –like solids.
B.
Solubility
o Alkanes, Alkenes and Alkynes are nonpolar compounds.
o Their solubility “ Like dissolve like”
o Alkanes, Alkenes and Alkynes are soluble in the nonpolar solvents;
carbon tetrachloride, CCl4 and benzene,
o Alkanes, Alkenes and Alkynes are insoluble in polar solvents like water.
Aliphatic Hydrocarbons
Physical Properties of Alkanes, Alkenes and
o Alkynes
Boiling Points & Melting Points
 Effect of Molecular Weight
The boiling points and melting points of normal hydrocarbons increase with increasing molecular
weight.
As the molecules become larger, there are more forces of attraction between them, and more
energy is needed.
 Effect of Branching
• Among isomers, straight chain compound has the
highest boiling point.
• The greater the number of branches, the lower the

boiling point.
22
Preparation of Alkanes 1. Alkanes
23
1. Hydrogenation of unsaturated hydrocarbon:
2. Hydrolysis of Grignard reagent
3. Reduction of Alkyl halides By lithium dialkyl cuprate

Reactions of Alkanes 1. Alkanes
24
Saturated hydrocarbons undergo very few reactions, so they are called Paraffinic
hydrocarbons. (Latin parum, little; affinis, affinity)
Combustion H
heat
C + O2 CO2 + H2O + heat
H
An alkane
Halogenation
The halogenation of an alkane appears to be a simple free radical substitution in
which a C-H bond is broken and a new C-X bond is formed 24
25
A. Halogenation
o Substitution reaction of
alkanes,
i.e. replacement of hydrogen by halogen,
usually chlorine or bromine, giving alkyl chloride or alkyl bromide.
o Flourine reacts explosively with alkanes
It is unsuitable reagent for the preparation of the alkyl flourides.
o Iodine is too unreactive
It is not used in the halogentaion of alkanes.
o Halogenation of alkanes take place at
high temperatures or under the influence of ultraviolet light
A)
Halogenation
o Chlorination of an alkane usually gives a mixture of products
o With longer chain alkanes, mixtures of products may be obtained even at the first step.
For example, with propane,
26
Uses of Alkanes
27
o Alkanes are unreactive compounds and mainly used as a source of energy;

Examples:
- Natural gas is composed mostly of methane, but it also contains small amounts of ethane, propane,
butane, and pentane.
- Diesel itself is a mixture of hydrocarbons, ranging from C 10H20, (decane) to C15H28.
o Petroleum jelly (Vaseline) is petrolatum, a hydrocarbon, C15H15N (1,1,2 Trimethylbenzeindole).
o Most petroleum jelly today is used as an ingredient in skin lotions and cosmetics.
o Paraffin wax (or petroleum wax) is a soft colorless solid, derived from petroleum, that consists of
a mixture of hydrocarbon molecules containing between twenty and forty carbon atoms.
o Common applications for paraffin wax include lubrication, electrical insulation, and candles
o Cyclopropane is used as an anaesthetic
o General uses;
- Making organic compounds and used as Organic solvents
28
2. ALKENES
Unsaturated Hydrocarbons
The Structure of 1. Alkenes
29
Alkenes
o Alkenes are hydrocarbons that contain a carbon–carbon double bond.
o Alkenes are also Olefins.
o General formula is CnH2n
o The simplest members of the Alkenes series are C2 & C3
o Hybridization; sp2-hybridized orbitals

o The angle between them is 120° and bond length C=C (1.34 Å).
o A trigonal planar.
Nomenclature; Common Names 1. Alkenes
30
o The simplest members of the alkene and alkyne series are frequently referred to by
their older common names, ethylene, acetylene, and propylene.
o Two important groups also have common names; They are the vinyl and allyl groups.
o These groups are used in common names.
Nomenclature; IUPAC Rules 1. Alkenes
31
The IUPAC rules for naming alkenes are similar to those for alkanes, but a few rules
must be added for naming and locating the multiple bonds.
1. The ending -ene is used to designate a carbon–carbon double bond.

2. Select the longest chain that includes both carbons of the double bond.
3. Number the chain from the end nearest the double bond so that the carbon
atoms in that bond have the lowest possible numbers.
32
If the multiple bond is equidistant from both ends of the chain, number the chain from
the end nearest the first branch point.
4. Indicate the position of the multiple bond using the lower numbered carbon
atom of that bond.
33
NOTE
S root of the name (eth- or prop-) tells us the number of carbons, and the ending
The
(-ane, -ene, or -yne) tells us whether the bonds are single, double, or triple.
No number is necessary in these cases, because in each instance, only
one structure is possible.
With four carbons, a number is necessary to locate the double bond.

34
o Branches are named in the usual way.

Example: Write the structural formula of 4-Isopropyl-3,5-dimethyl-2-octene.
1) The parent carbon chain is an Octene.
The double bond is located between the 2nd and 3rd carbons.
2) Two methyl groups are attached on the parent carbon chain, one on carbon 3
and the other on carbon 5.
3) An isopropyl group is attached on carbon 4.
4) Put the missing hydrogens to get the correct structure.

35
Nomenclature of Cycloalkenes 1. Alkenes
o We start numbering the ring with the carbons of the double bond.
o A number is not needed to denote the position of the functional group, because the
ring is always numbered so that the double bond is between carbons 1 and 2.
o Put the lowest substituent number into the name not in the direction that gives the
lowest sum of the substituent numbers.
6 2
2 5 CH3 3 CH3
3 CH2CH3 1 1
1
2 4 6
4
5 4 3 CH3 CH2CH3
5
Cyclopentene 3-Ethylcyclopentene 4,5-Dimethylcyclohexene 4-Ethyl-3-methylcyclohexene

X
2-Cyclopentene
X
5-Ethylcyclopentene
36
Isomerism
37
o Isomers are different compounds with identical molecular formulas.

o The phenomenon is called isomerism.
Types of Isomerism
Structural Geometrical
Isomerism Isomerism
Alkanes  Alkenes
 Cycloalkanes
Isomerism
Structural Isomerism in
38
Alkanes
o Structural or constitutional isomers are isomers which differ in the sequence of
atoms bonded to each other.
 Examples:
• Butanes, C4H10
• Pentanes, C5H12
Isomerism
Geometric Isomerism in
39
Alkenes
o In alkenes, geometric isomerism is due to restricted rotation about the carbon - carbon double
bond.
A) when W differs from X and Y from Z, Alkenes exist as geometric

isomers
 cis isomer; when two similar groups are on the same side or same side of the double bond.
 trans isomer; when two similar groups are on the opposite direction or opposite sides of the
double bond.
• They have different physical properties and can be separated by fractional crystallization or distillation.
Isomerism
40
Alkenes
B) If (W = X or Y = Z), geometric isomerism is not possible.
Isomerism
41
o
Alkenes
For alkenes with four different substituent such as
Another system, the E, Z

system,
o Basically, the E,Z system works as follows;
Arrange the groups on each carbon of the C=C bond in order of priority
o The priority depends on atomic number:
The higher the atomic number of the atom directly attached to the double-bonded
carbon, the higher the priority.
Thus, in structure (I),
Cl > F, and CH3 > H.
Isomerism
42
Alkenes
o If the two groups of higher priority are on the same side of the C=C plane,
The isomer is labeled Z; (from the German zusammen, together).
o If the two groups of higher priority are on opposite sides of the C=C plane,
The isomer is labeled E; (from the German entgegen, opposite).
Isomerism
43
Cycloalkanes
cis-trans Isomerism in
Cycloalkanes
cis–trans isomerism (sometimes called geometric isomerism) is one kind of
stereoisomerism.
Preparation of
Unsaturated hydrocarbons
o Unsaturated hydrocarbons are prepared by Elimination of an atom or group of atoms
from adjacent carbons to form carbon-carbon double or triple bond.
1) Dehydration of Alcohols
When an alcohol is heated in the presence of a mineral acid catalyst,

It readily loses a molecule of water to give an alkene.
44
Preparation of Unsaturated
hydrocarbons (Alkenes)
The acid catalysts most commonly

used are mineral acids as sulfuric
acid, H2S04, and phosphoric acid,
H3P04.
o Removal of OH group and a proton from two adjacent carbon atoms using mineral
acids such as HCl, H2SO4 and H3PO4
45
1) Dehydration of Alcohols hydrocarbons (Alkenes)
46
Which Alkene Predominates?; Saytzeff’s Rule

The loss of water from adjacent carbon atoms, can give rise to more than one alkene.
Example: the dehydration of 2-butanol.
2-butene is the major (with two

alkyl substituents attached to
C=C)
Saytzeff’s Rule
applies
In every instance in which more than one Alkene can be formed
The major product is always the alkene with the most alkyl substituents attached on
the double-bonded carbons.
1) Dehydration of Alcohols hydrocarbons (Alkenes)
47
o Classes of Carbocations
according to the number of carbon atoms attached to the positively charged carbon.
o Generall
1.y The dehydration of alcohols requires an acid catalyst.
2. The predominant alkene formed follows Saytzeffs rule.
3. The reaction proceeds via a carbocation intermediate.
4. The stabilities of carbocations and the ease of dehydration of alcohols
follows the order 3° > 2° > 1°.
2) Dehydrohalogenation of Alkyl hydrocarbons (Alkenes)
48
Halides
o Alkenes can also be prepared under alkaline conditions.
heating an alkyl halide with a solution of KOH or NaOH in alcohol, yields an
alkene.
3) Dehalogenation of Vicinal Dibromides

Reactions of Unsaturated
hydrocarbons
(1) Electrophilic Addition
Reactions
Addition of Symmetric and Unsymmetric Reagents to symmetric Alkenes.

1. Addition of Hydrogen: Catalytic Hydrogenation
2. Addition of Halogens: Halogenation
Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov’s Rule.
1. Addition of Hydrogen Halides
2. Addition of Sulfuric Acid
3. Addition of Water: Hydration
4. Addition of HOX: Halohydrin Formation
(2) Oxidation Reactions
1. Ozonolysis 49
2. Oxidation Using KMnO4
Electrophilic Addition hydrocarbons (Alkenes)
50 Reactions
1. Addition of Hydrogen:
Hydrogenation
Addition of a mole of hydrogen to carbon-carbon double bond of Alkenes in the
presence of suitable catalysts to give an Alkane.
51
Reactions
2. Addition of Halogen:
Halogenation
When an alkene is treated at room temperature with a solution of bromine or chlorine
in carbon tetrachloride to give the corresponding vicinal dihalide (two halogens
attached to adjacent carbons)
Br2/CCl4 Br
Br
1,2-Dimethyl-cyclohexene trans-1,2-Dibromo-1,2-dimethyl-cyclohexane
52
Reactions
3. Addition of Acids
o A variety of acids add to the double bond of alkenes.
The hydrogen ion (or proton) adds to one carbon of the double bond, and the
remainder of the acid becomes connected to the other carbon.
o Acids that add in this way are the hydrogen halides (H-F, H-Cl, H-Br, H-I), and
water (H-OH).
o Reactions
Any electron-deficient species is called an electrophile.
o Any electron-rich species is called a nucleophile.
Examples of Electrophile:
i) Positive reagents: protons (H+), alkyl group R+ , nitronium ion (NO2+), etc….
ii) Neutral reagents having positively polarized centers: HCl, bromine (because it can be
polarized so that one end is positive).
iii) Lewis acids: molecules or ions that can accept an electron pair  BF3 and AlCl3.
Examples of Nucleophile:
a)Negative ions e.g. HO Hydroxide ion, HS Hydrosulphide ion, RO Alkoxide ions,
N C Cyanide ion, X Halide ions, ...etc.

b) Neutral molecules
e.g. H2O , R O H, R O R , H3N , R3N , ...etc.

53
54
Reactions
3. Addition of Acids
o The addition of H—A to an alkene is believed to be a two-step process.
Step 1. The hydrogen ion (the electrophile) attacks the ∏-electrons of
the alkene, forming a C—H bond and a carbocation.
Step 2. The negatively charged species A: - (a nucleophile) attacks the

carbocation and forms a new C—A bond.
o The attack by an electrophilic reagent on the ∏-electrons, falls in a general

category called electrophilic addition reactions.
55
Reactions
3.1. Addition of Hydrogen
Alkenes reactHalide
with hydrogen chloride, HC1, hydrogen bromide, HBr and hydrogen
iodide, HI, to form alkyl halides, RX.
Examples
;
56
Reactions
o Reagents and alkenes can be classified as either symmetric or unsymmetric with
respect to addition reactions.
 If a reagent and/or an alkene is symmetric, only one addition product is possible.
 But if both the reagent and the alkene are unsymmetric, two products are, in
principle, possible.
57
Reactions
Markovnikov’s
Rule
In electrophilic addition of H—X to Unsymmetrical Alkenes the hydrogen of the hydrogen
halide adds to the double-bonded carbon that bears the greater number of hydrogen atoms and
the negative halide ion adds to the other double-bonded carbon.
58
Reactions
Explanation for Markovnikov’s
Rule
Example; Addition of HBr to propene
o In modern terms Markovnikov’s rule can be restated:

The addition of an unsymmetrical reagent HX to an unsymmetrical alkene
proceeds in such a direction as to produce the more stable carbocation.
59
Reactions
3.2. Addition of Water:
Hydration
If an acid catalyst is present, water (as H-OH) adds to alkenes and the product is alcohol.
Oxidation Reactions hydrocarbons (Alkenes)
1.Ozonolysis
o Ozonolysis can be used to locate the position of a double bond.
o Example, ozonolysis of 1-butene gives two different aldehydes, whereas 2-butene
gives a single aldehyde.
60
Oxidation Reactions hydrocarbons (Alkenes)
61
2. Oxidation Using KMnO4

Alkenes react with alkaline potassium permanganate to form glycols (compounds with
two adjacent hydroxyl groups).
Uses of Alkenes
62
SYNTHETIC POLYMERS
Synthetic polymers are produced when small molecules called monomers bond together to
form a much smaller number of very large molecules.
An important example:
- Polyvinylchloride; manufacture of water and sewer pipe.
- Polyethylene (plastic bags, milk cartons),
- Polypropylene, (impact-resistant plastics, indoor-outdoor carpeting),
- Polyacrylonitrile (Orlon, carpets),
- Polystyrene (foam insulation)
63
3. ALKYNES
The Structure of 2. Alkynes
64
Alkynes
o Alkynes are hydrocarbons that contain a carbon–carbon triple bond.
o Alkynes are also known as Acetylenes.
o General formula is CnH2n-2
o Hybridization; sp-hybridized orbitals
o The angle between them is 180° and
the bond length 1.20 A°
o The geometry is Linear.
The Structure of 2. Alkynes
65
Alkynes
o The simplest members of the Alkynes series are C2 & C3
o The IUPAC names are derived from the corresponding alkanes by replacing the –ane
ending by –yne.
o IUPAC rules as discussed for Alkenes .
o Example:
3-Chloro-2,7-dimethyl-4-nonyne
Acidity of Alkynes 2. Alkynes
66
o A hydrogen atom on a triply bonded carbon (Terminal Alkyne) is weakly acidic and
can be removed by a very strong base ( as Sodium amide).
o Internal alkynes (Non-Terminal Alkyne) have no exceptionally acidic hydrogens.

- Relative Acidity of the Hydrocarbon.
Terminal alkynes, are more acidic than other hydrocarbons
1) Dehydrohalogenation of Preparation of Unsaturated
Alkyl dihalides hydrocarbons (Alkynes)
67
Alkynes can be prepared under alkaline conditions via deydrohalogenation of alkyl

dihalides
2) Reaction of Sodium AcetylidePreparation of Unsaturated
with Primary Alkyl Halides hydrocarbons (Alkynes)
68
o Acetylene
o Monosubstituted Acetylenes
Electrophilic Addition hydrocarbons (Alkynes)
69
Reactions
1. Addition of Hydrogen: Hydrogenation
o With an ordinary nickel or platinum catalyst, alkynes are hydrogenated all the way to
alkanes.
o However, a special palladium catalyst (called Lindlar’s catalyst) can control hydrogen
addition so that only one mole of hydrogen adds. In this case, the product is a cis
alkene.
o On the other hand, reduction using metals such a s sodium or lithium in liquid ammonia
results in formation of trans alkenes.
70
Reactions
2. Addition of Halogen: Halogenation
Bromine adds as follows; In the first step, the addition occurs mainly trans.
3. Addition of Hydrogen Halide

With unsymmetrical triple bonds and unsymmetrical reagents, Markovnikov’s
Rule is followed in each step, as shown in the following example:
71
Reactions
4. Addition of Water:
o Hydration
Addition of water to alkynes requires not only an acid catalyst but mercuric ion as well.
o The mercuric ion forms a complex with the triple bond and activates it for addition.
o Although the reaction is similar to that of alkenes, the initial product - a vinyl alcohol or enol
- rearranges to a carbonyl compound (keto form).
Uses of Alkynes
72
Alkynes;
- Ethyne or acetylene reacts with oxygen to produce enough heat to weld metals.
- Anti-tumor agent
Many alkynes are dangerous for humans when used in pharmaceuticals. However, specific
alkynes, known as ene-diynes, hold a very strong and aggressive anti-tumor compound.
Calicheamicin is an example of an anti-tumor working agent
- Drug production
Alkynes are used in the manufacture of many drugs on the market, such as antiretroviral efavirenz and
the antifungal terbinafine.
- General uses;
- Making organic compounds
- Organic solvents

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Fundamentals of Organic Chemistry

CHEM 109 CHAPTER 2. ALIPHATIC HYDROCARBON

At the end of this chapter, students will able to:

 Alkynes : Cn H2n-2 (contain carbon-carbon triple bond)

The longest continuous chain is not necessarily straight.

o If only one substituent is present, no number is needed to locate it.

• The greater the number of branches, the lower the

1. Hydrogenation of unsaturated hydrocarbon:

2. Hydrolysis of Grignard reagent

3. Reduction of Alkyl halides By lithium dialkyl cuprate

o Alkanes are unreactive compounds and mainly used as a source of energy;

o Hybridization; sp2-hybridized orbitals

1. The ending -ene is used to designate a carbon–carbon double bond.

With four carbons, a number is necessary to locate the double bond.

o Branches are named in the usual way.

3) An isopropyl group is attached on carbon 4.

4) Put the missing hydrogens to get the correct structure.

Cyclopentene 3-Ethylcyclopentene 4,5-Dimethylcyclohexene 4-Ethyl-3-methylcyclohexene

o Isomers are different compounds with identical molecular formulas.

A) when W differs from X and Y from Z, Alkenes exist as geometric

Another system, the E, Z

When an alcohol is heated in the presence of a mineral acid catalyst,

The acid catalysts most commonly

Which Alkene Predominates?; Saytzeff’s Rule

2-butene is the major (with two

3) Dehalogenation of Vicinal Dibromides

Addition of Symmetric and Unsymmetric Reagents to symmetric Alkenes.

N C Cyanide ion, X Halide ions, ...etc.

e.g. H2O , R O H, R O R , H3N , R3N , ...etc.

Step 2. The negatively charged species A: - (a nucleophile) attacks the

o The attack by an electrophilic reagent on the ∏-electrons, falls in a general

o In modern terms Markovnikov’s rule can be restated:

2. Oxidation Using KMnO4

o Internal alkynes (Non-Terminal Alkyne) have no exceptionally acidic hydrogens.

Alkynes can be prepared under alkaline conditions via deydrohalogenation of alkyl

3. Addition of Hydrogen Halide

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