For the First Year of Senior High School

2007

Introduction
Alkane, alkene, alkyne

Specification of Carbon Atom

Isomers

The Position of Carbon Atoms on Hydrocarbon Compounds

A reactions of hydrocarbon
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Hydrocarbon

You will test the existence of carbon, hydrogen and oxygen elements in hydrocarbon compounds

You will know the specific characteristics of carbon literally

You will read the literatures to know about the properties of hydrocarbon

You will read the literatures in order to know the reactions on hydrocarbon

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Do you know about these stuffs?

drugs

food

Petroleum for car Those belong to the realm of a field known as ORGANIC
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CHEMISTRY
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The difference between organic and inorganic compounds

Organic compound The reaction happens among the molecules by easy-stages. 2. The boiling point and the melting point are low. 3. If heated, it can be decomposed easily. 4. Its molecules can make isomeric structure. 5. Its solvent is commonly organic compound.
1.

Inorganic compound 1. The reaction happens among the ions swiftly. 2. The boiling point and the melting point are high. 3. It is stable when heated. 4. Its molecules cant make isomeric structure. 5. Its solvent is commonly water.

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Specification of Carbon Atom

Carbon compounds are found abundantly because carbon is capable of making carbon atomic chain and forming various types of bond, such as single bond, double bond and also triple bond. Here are the physical properties of Carbon

Electronic configuration

1s2 2s2 2p2

Electronegativity
Covalent radius

2.55
0.077 nm

In periodic system of elements, carbon (Z=6) lies at the 2nd

period of group

IVA.

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That position (both period and group), gives special natures to carbon, they are:

1). Carbon has four valence electrons

Carbon has four valence electrons and it must either gain four electrons or lose four electrons to reach a rare-gas configuration. The electronegativity of carbon is too small for carbon to gain electrons from most elements to form C4- ions, and too large for carbon to lose electrons to form C4+ ions. Carbon therefore forms covalent bonds with a large number of other elements, including the hydrogen, nitrogen, oxygen, phosphorus, halogen group (F, Cl, Br, I) and sulfur found in living systems. Notice some examples in the following picture.
xx

xx

CH4 carbon methane

CH3OH methanol

Lewis structure of some carbon compounds document of bu emmy

. .C. .

H x. H C H x. H
x.

H x . xx H C O H xx H
x.

Cl x . xx H C Cl x . xx Cl
x x . xx

xx

x . xx N H C x. H x. H H

xx

x. x. . x

xx

x.

x.

cloroform

xx

CHCl3

CH3NH2 methylamine

2). Small Carbon Atom Relative According to its periodic number, carbon atom only has 2 atom shells so that its radian is relatively small. This results in: a. Relatively strong covalent bonds The valence electron of carbon atom is so close to a nucleus that the bounding is difficult to break. Its because the nucleus attractive force to the electron is quite strong. b. Capability to form double or triple bonds Because they are relatively small, carbon atoms can come close enough together to form strong C=C double bonds or even CC triple bonds.

The Position of Carbon Atom on Hydrocarbon Compounds

The carbon atom can form long chains or rings. Carbon, which has four valence electrons, can form a bonding with other carbons. This is called a carbon chain. The chain has three types; straight chain, branched chain and closed/ ring chain.
C C C C C C HC

C C

straight chain

branched chain

C C C C C C

ring/ closed chain

Based on the number of carbon atom bonded with others, there are 4 kinds of carbon atoms: a. Primary Carbon Atom (10): Carbon atom which is bonded with another carbon atom. b. Secondary Carbon Atom (20): Carbon atom which is bonded with two carbon atoms. c. Tertiary Carbon Atom (30): Carbon atom which is bonded with three carbon atoms d. Quaternary Carbon Atom (40): Carbon atom which is bonded with four carbon atoms.
Tertiary Carbon Atom C C H C CH3 C C H2 H H C C C H2 Quaternary Carbon Atom Primary Carbon Atom

Secondary carbon atom

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The bounding in carbon atom chain is divided into 2 forms, they are: a. Saturated bounding or a single bounding This happens when 2 carbon atoms gives 1 electron to be used together. For example:

a single bounding

b. Unsaturated bounding (double/ triple bounding) This happens if the carbon atoms give more than 1 electron to be used together.

Unsaturated bounding is distinguished into 2 forms, they are: 1). A double bounding. It uses 2 electrons to be used together. For example: double bounding

2). A triple bounding. It uses 3 electrons to be used together. For example:

triple bounding

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Based on the shape of carbon chain, carbon compounds can be distinguished into aliphatic compound and cyclic compound.
a. Aliphatic compound Aliphatic compound is an open-chain carbon compound. It has 2 kinds of compounds, they are: 1). Saturated aliphatic compound, which its carbon-chain is a single bounding. For example:
C C C C C C C

straight-chain

branched-chain

2). Unsaturated aliphatic compound, which its carbon-chain is a double bounding or a triple bounding. For example:
C C C C C C

double bounding

triple bounding

b. Cyclic compound Cyclic compound is a round (ring) chain carbon compound. 1). Carbocyclic; cyclic compound which its ring chain consists of only carbon atom. a). Aromatic compound is a carbocyclic compound that has conjugation bounding, that is single and double bound in alternate position. For example:
C C C C C C or or

b). Alcyclic compound is a carbocyclic compound which has the same characteristics with aliphatic compounds. For example:
C C C C C C C C

2). Heterocyclic; cyclic compound which its ring chain consists of carbon atom and other atoms. For example:
H N H2C H2C C H2 CH2 CH2

H2C H2C N

CH2 CH

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Hydrocarbon
Hydrocarbon is the simplest group of carbon compounds. Hydrocarbon consists of two types of element that is Carbon (C) and hydrogen (H). Although consisting of two types of element only, hydrocarbon constitutes a big group of compound. This is because of its capability to form an atom chain in various types and bond. Methane (CH4) is the simplest compounds of hydrocarbon.

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ALKANES, ALKENES, ALKYNES

1. ALKANES
Hydrocarbon that contain as many hydrogen atoms as possible are said to be saturated. The saturated hydrocarbons are also known as alkanes.

The generic formula for alkanes:

CnH2n+2
The names, formulas, and physical properties for a variety of alkanes are given in the table. The boiling points of the alkanes gradually increase with the molecular weight of these compounds. At room temperature, the lighter alkanes are gases; the midweight alkanes are liquids; and the heavier alkanes are solids, or tars.

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Name methane ethane propane butane pentane hexane heptane

Molecular Formula CH4 C 2H 6 C 3H 8 C4H10 C5H12 C6H14 C7H16

octane
nonane decane

C8H18
C9H20 C10H22
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Alkyl Cluster

Compounds like methane, CH4, and ethane, CH3CH3, are members of a family of compounds called alkanes. If you remove a hydrogen atom from one of these you get an alkyl group. These groups must, of course, always be attached to something else. We can name the alkyl by substituting ane of alkanes with yl. The general formula for alkyl is:

CnH2n+1

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Skeleton Structure

Formulae CH3

Name methyl

H 3C

H 3C

C H2

C2H5

ethyl

H3C

C H2 C H2 H C

C H2 C H2

C3H7

propyl

H 3C

C4H9

butyl

H 3C

CH3 H3C C H2

C H2 H C CH3

C4H9

isobutyl

C4H9

secondarybutyl

CH3 H 3C C CH3 C4H9 tertierybutyl

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Nomenclature of alkanes

Nomenclature of alkanes is divided into 2 systems: (a) Trivial (trade name) The rule to name alkanes according to TRIVIAL: 1. The straight chain alkanes, is given a prefix called normal (n). For examples:
H3C C H2 C CH3 H2 n-butane

2. The branched chain alkanes, the name of substituents are begun by neo or iso. H For example:
H3C C CH3 isobutane CH3 CH3 H3C C
3

CH3

neopentane
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(b) IUPAC (systematic nomenclature) 1). The straight chain alkane, its nomenclature is based on the amount of C atoms. For examples:
H 3C C H2 CH3 propane

CH3 CH3 H 2C CH2 butane

2). The branched chain alkanes.

a) Find the longest continuous chain of carbon atoms in the skeleton structure. Name the compound as a derivative of the alkane with this number of carbon atoms.

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b) The carbon atom being outside of main chain (substituent) is called alkyl c) By numbering carbon atom on the main chain coming from the carbon atom which is the closest with the substituents.

For example:
H 3 C H24C

H31C

C H2

C H2
5

CH3

ethyl is bounded by the carbon atom number 3

CH2 CH3 there are 6 carbon atom for the main chain = hexane

name: 3 ethyl-hexane

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d) Number the chain starting at the end nearest the first substituent and specify the carbon atoms on which the substituents are located. Use the lowest possible numbers. This compound, for example, is 2methylpentane, not 4-methylpentane.

For example:

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e) Use the prefixes di-, tri-, and tetra- to describe substituents that are found two, three, or four times on the same chain of carbon atoms. For example:

CH3 CH2 H3 C
8 7

ethyl

C H2

H 6 C CH3 methyl

C H

H 4 C H 3C CH3 methyl

C H2 H 2 C CH3

CH3
1

ethyl

CH3

methyl

name : 4,5-diethyl-2, 3, 6-trimethyloctane

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f) Arrange the names of the substituents in alphabetical order. For example:

methyl H3C H31C
2

H 3 C CH2

C H2

H 5 C H26C

C H2 7 C H2

CH3
8

ethyl

CH3

name: 5-ethyl-3-methyl octane

g) If one carbon atom on main chain bounds 2 alkyls (substituents), the numbering is repeated.One without courage is like a car without fuel For example:
CH3 H 31C
2

C2H5
3

ethyl is bounded by 4th carbon atom

5

CH3

C H2

CH3

C H2

C H2

CH3

Name:

methyl is bounded by 2nd and 4th carbon atoms 4-ethyl-2,2,4-trimethylheptane of bu emmy document

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h) If we find some alternatives of the longest carbon chain, we should choose the carbon chain having the most alkyl. For example: H 5 4 3 H3 C C C CH3 ethyl C H2 H2 H3C 2CH methyl 1 CH3

name: 3-ethyl-2-methylpentane

NOT 3-isopropylpentane

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2. ALKENES Compounds that contain C=C double bonds were once known as olefins (literally, "to make an oil") because they were hard to crystallize (They tend to remain oily liquids when cooled). These compounds are now called alkenes.
Alkenes have general formula:

CnH2n

Hydrocarbon having 2 double bounds is called alkadiene and having 3 double bounds is called alkatriene. You can changes the suffix ane on alkanes with the suffix ene to become alkenes. Alkenes are examples of unsaturated hydrocarbons because they have fewer hydrogen atoms than the corresponding alkanes. They were once named by adding the suffix -ene to the name of the substituent containing the same number of carbon atoms.

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Here are the names for some compounds of alkenes:

Name

Molecular Formula

ethene
propene butene pentene

C2H4
C3H6 C4H8 C5H10

hexene
heptene octene nonene

C6H12
C7H14 C8H16 C9H18

decene

C10H20

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Nomenclature of alkenes

a. For straight chain of alkenes, numbering of carbon atom starts/ begins from the nearest double bound. The presence of the C=C double bound is indicated by changing the -ane ending on the name of the parent alkane to -ene. The location of the C=C double bond in the skeleton structure of the compound is indicated by specifying the number of the carbon atom at which the C=C bond starts. For example:

H2C

2
C H

C H2

CH3

H2C

3
C H2

4
CH3

C H

n-butene
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2-butene
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b. For branched chain of alkenes:

1. Find the longest continuous chain of carbon atoms in the skeleton structure which has double bounding. 2. Carbon atom numbers starts from the nearest double bound. 3. The names of substituents are then added as prefixes to the name of the alkene. For example:
CH3 H 3C
5

C H2

C H

C H

CH3

main chain

CH3

5,5-dimethyl-2-hexene

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4. If the double bounding on a compound has the same distance from the both edges, name the compound from the nearest substituents.
For example:
H31C
2 3 4

C CH3

C H

CH3

2-methyl-2-butene
5. If the compound has 2 double boundings, name it using the suffix diena, and triena for 3 double boundings. For examples:
H2C C CH3 C H CH2 H2C C CH3 C H C C H CH3

2-methyl-1,3-butadiene

2-methyl-1,3,4-hexatriene

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3. ALKYNES

Compounds that contain C C triple bonds are called alkynes. These compounds have four less hydrogen atoms than the parent alkanes, so the generic formula for an alkyne with a single C C triple bond is CnH2n-2. The simplest alkyne has the formula C2H2 and is known by the common name acetylene.

CnH2n-2

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Nomenclature of alkynes

The IUPAC nomenclature names alkyne compounds as derivatives of the parent alkaneswith the ending -yne replacing -ane.

In addition to compounds that contain one double bond (alkenes) or one triple bond (alkynes), we can also envision compounds with two double bonds (dienes), three double bonds (trienes), or a combination of double and triple bonds.

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The names of substituents are then added as prefixes to the name of the alkyne.

CH3 CH3 H 31C

2

H2

C H

C H2

CH3

main chain

CH2 CH3

3-ethyl-3,4-dimethyl-1-hexyne

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4. THE PROPERTIES AND THE ADVANTAGES OF HYDROCARBON All of the hydrocarbon compounds (alkane, alkene and alkyne) have the same properties, they are: a) Hydrocarbon is non-polar so that it cant be dissolved in water. Hydrocarbon is dissolved in non polar compounds, such as CCl4 or ether. b) The longer the carbon atom chain, the higher the boiling point is. If the carbon atom chain is getting longer the bounding is getting strong, or we can say that in homologous, the bigger the relative molecule mass (Mr), the higher the boiling point is. c) If the compounds have the same relative molecule mass (Mr), the straight chain hydrocarbon has higher boiling point than the branched chain hydrocarbon. The branch on hydrocarbon chain will disturb the bounding stability.

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Alkane
Methane

Boiling point (0C)

Alkene

Boiling Alkyne point (0C)

Boiling point (0C)

-162 Ethane -88,5 Propane -42 Butane 0 Pentane 36

Ethane Propene 1-butene 1pentene 1-hexene

-102 -48 -6 30 63,5

Ethyne Propyne Butyne Pentyne Hexyne

-75 -23 8,1 40,2 71,3

The advantage of hydrocarbon compounds:

1) Alkane can be used as a fuel. 2) Alkene can be used to make a synthetic material, such as plastic. 3)The most important alkyne is acetylene coming from carbide gas (see to the reaction below) and can be used to weld metals. CaC2 + 2H2O Ca(OH)2 + C2H2 Ethyne/ acetylene
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ISOMERS

Isomers are molecules that have the same molecular formula, but have a different arrangement of the atoms in space. They exclude any different arrangements which are simply due to the molecule rotating as a whole, or rotating about particular bonds. For example, both of the following models are the same molecule. They are not isomers. Both are butane.

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There are also endless other possible ways that this molecule could twist itself. There is completely free rotation around all the carbon-carbon single bonds. Here are some examples of isomers:
H C CH3

H 3C

C H2

C H2

C H2

CH3

H 3C

C H2

CH3

n-pentane
CH3 H 3C C CH3 CH3

2-methylbutane

2,2-dimethylpentane

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a. Structural isomers
In structural isomerism, the atoms are arranged in a completely different order. This is easier to see with specific examples.

For examples, Pentane, C5H12, has three chain isomers. If you think you can find any others, they are simply twisted versions of the ones below. If in doubt make some models.

Another example is butene (C4H8), has 3 chain isomers.

H2C C H C H2 CH3 H3C C H C H CH3

1-butene

2-butene

H2C

C CH3

CH3

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b. Geometric isomers
Geometric isomers are isomers in which the atoms are connected in the same way, but differ in the way the atoms are arranged in space. There are two kinds of geometric isomers, cis and trans. Cis : The isomer with similar substituents on the same side of the double bond, a Latin stem meaning "on this side." Trans : The isomer in which similar substituents are across from each other, a Latin stem meaning "across." For example: The cis isomer of 2-butene, for example, has both CH3 groups on the same side of the double bond. In the trans isomer the CH3 groups are on opposite sides of the double bond.

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A reactions of hydrocarbon 1. Substitution reaction

Substitution means to change. Substitution reaction therefore defines as a changing reaction of one atom to another. It usually happens on saturated hydrocarbon such as alkane. In the presence of light, or at high temperatures, alkanes react with halogens to form alkyl halides. Reaction with chlorine gives an alkyl chloride. light CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)

Reaction with bromine gives an alkyl bromide. light CH4(g) + Br2(l) CH3Br(g) + HBr(g)

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2. Addition reaction
An addition reaction is a reaction in which two molecules join together to make a bigger one. Nothing is lost in the process. All the atoms in the original molecules are found in the bigger one. In addition reaction, an unsaturated bounding is changed into saturated one. This means that addition reaction only happens on alkene and alkyne.

X R C H
For example:

Y C H R

C H

C H

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Addition reactions provide a way to add new substituents to a hydrocarbon chain and thereby produce new derivatives of the parent alkanes. In 1870, after careful study of many examples of addition reactions, the Russian chemist Valdimir Markovnikov formulated a rule for predicting the product of these reactions.

Markovnikov's rule states that the hydrogen atom adds to the carbon atom that already has the larger number of hydrogen atoms when HX adds to an alkene.

For example:
H3C C H CH2 + it bounds 2 H it bounds 1 H 1-propene
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HCl

H3C

H C Cl

CH3

2-chloropropane
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3. Elimination reaction
In elimination reaction, a saturated bounding is changed into an unsaturated one by losing the atoms. It usually happens on alkane. For example:

H 3C

C H2

C H2

CH3

H 3C

C H2

C H

CH2

H2

butane

butene

4. Polymerization reaction
Polymerization is a combination of two or more separate molecules to form a more complex molecule. Alkene can make a polymerization, e.g PVC (polyvinyl chloride) is formed by a monomer of chloroetene

CH2=CH-Cl + CH2=CH-Cl

[CH2-CHCl-CH2-CHCl]n
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5. Oxidation reaction
An oxidation reaction is also called as a combustion reaction. In this reaction, hydrocarbon is reacted by oxygen. In a complete combustion, C atom is burned and turned into CO2, while H turns into H2O. An incomplete combustion results in CO and H2O. The reactions of complete combustion:
CH4(g) + 2 O2(g) CO2(g) + 2 H2O(g)

The reaction of incomplete combustion:

C2H4(g) + 2 O2(g)

2CO(g) + 2 H2O(g)

An energy coming from a complete combustion is used as energy resources such as LNG (C1-C4), LPG (C3-C4), gasoline (C5-C12) and kerosene (C10-C16). The oxidation reaction can be used to identify the amount of carbon atoms in compounds.

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For example: On a combustion of 7,5 gram of alkane results in 132 gram of CO2 and 72 gram of water. Determine the molecular formula of those alkanes! The solution:

CxHy

O2

CO2 + H2O

CO2
H 2O

g 132 3 mole Mr CO2 44

g 72 4 mole Mr H 2O 18

Mole of CO2 : mole of H2O = coef of CO2 : coef of H2O So, the reaction becomes: CxHy + O2 3CO2 + 4H2O Cx = 3 C x=3 Hy = 8 H y=8 So, a burned alkane is C3H8 (propane).
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