Chapter one Alkanes

An alkane is hydrocarbon that contains only single bonds .The alkanes are simplest & least reactive class of organic compounds, because they contain only carbon & hydrogen &they have no reactive functional groups. Althought alkanes undergo reactions such as cracking & combustion at high temperature , they are much less reactive under most conditions than other classes of compounds having functional groups .

1.1

Classification of Hydrocarbon

Hydrocarbons are classified according to their bonding . A hydrocarbon with a carbon_carbon double bond(such as ethylene) is called alkane. If a hydrocarbon has a carbon__carbon triple bond (like acetylene) ,it is called alkyne.Hydrocarbons with aromatic (benzene like ) rings are called aromatic hydrocarbons .If a hydrocarbon has no double or tripge bonds , it is said to be saturated because it has the maximum number of bonded hydrogens.Another way to describe alkanes ,then,is as the class of saturated hydrocarbons. Summary of hydrocarbon classification :-

Compound type Alkanes Alkenes Alkynes

Functional Group Group C-C CH3CH2CH3 propane C=C CH2=CH-CH3 propene CC CH3-CC-H propyne

1.2Molecular formula of alkanes: The structure of the alkanes in the table 1-1 are purposely written in an unusual manner .The general formula for the n-alkanes in achain of ch2- groups (methylene groups ),terminated at each end by a

hydrogen atom.The n-alkanes differ only by the number of methylene groups in the chain .If the molecule contains n carbon atoms ,it must contain (2n+2) hydrogen atoms.&the formulas of the form CnH2n+2.

2s

2px 2py 2pz

2s

2px 2py 2pz

1s 2s 2p 2p 2p

Hybridisation

1s

sp3

sp3

sp3

sp3

Table 1.1

d M.P cm3 -182.5 -183.3 -187.7 -138.3 -129.8 -95.3 -90.6 -56.8 -53.5 -29.7 -25.6 -9.6 -5.5

B.P

Structure

name

formula

No.of C 1 2 3 4 5 6 7 8 9 10 11 12 13

.5572 .6603 .6837 .7026 .7177 .7299 .7402 .7487 .7546

CH4 methane CH4 167.7 -88.6 CH3CH3 C2H6 -42.1 CH3CH2CH3 C3H8 -0.5 CH3CH2 CH2CH3 C4H10 36.1 CH3CH2 CH2 CH2CH3 C5H12 68.7 CH3CH2 CH2 CH2 CH2CH3 C6H14 98.4 CH3CH2 CH2 CH2 CH2 CH2CH3 C7H16 127.7 CH3CH2 CH2 CH2 CH2 CH2 CH2CH3 C8H18 CH3CH2 CH2 CH2 CH2 CH2 CH2 150.8 C9H20 CH2CH3 CH3CH2 CH2 CH2 CH2 CH2 CH2 174.0 C10H22 CH2 CH2CH3 CH3CH2 CH2 CH2 CH2 CH2 CH2 195.8 C11H24 CH2 CH2 CH2CH3 CH3CH2 CH2 CH2 CH2 CH2 CH2 216.3 C12H26 CH2 CH2 CH2 CH2CH3 CH3CH2 CH2 CH2 CH2 CH2 CH2 235.4 C13H28 CH2 CH2 CH2 CH2 CH2CH3

1.3A Nomenclature of Alkanes The names methane,ethane,propane,and butane have historical roots. From pentane on,alkanes are named using the Greek word for the number of carbon atoms, plus the siffix-ane to identify the molecule as an alkane.
CH3C(CH3) 2CH3 CH3CH2CH3 CH3CH3 CH4 ( propane)( ethane) (methane) (neopentane)
H H C H H C CH3 H C H H H H C H H C H H C H H C H H

isobutane
H H C H CH3 C CH3 H C H H H H C H H C H H C CH3 H C H H

butane

H H C H

H C H

H C H

H C H

H C H H

neopentane

isopentane

pentane

1.3B IUPAC or Systematic Name RULE1: Find the longest continuous chain of carbon atoms, and use the name of this chain as the base name of the compound.
Hex Hept Oct Non Dec 6 7 8 9 01 Meth Eth Prop Buta Pent 1 2 3 4 5

RULE2: Number the longest chain beginning with the end of the chain nearest a substituent. RULE3: Name the substituent groups attached to the longest chain as alkyl groups . Give the location of each alkyl group by the number of the mainchain carbon atom to which it is attached. RULE4: When two or more substituents are present, list them in alphabetical order. When two or more of the same alkyl substituents are present, use the prefixes di, tri, tetra and so on. di- means 2 tri-means 3 tetra-means 4

H.W
1- Give the structures of 2-ethylhexane 2- Name the following alkanes a- CH3C(CH3) 2CH3 b-CH3CH2 CH(CH3 )CH2CH3 c- CH3CH(CH2CH3) CH3

3-write the structures for the following compounds a- 3-ethyl-3-methylpentane b-3-methyl-5-propylnonane

1.4 uses and sources of alkanes. C1-C2. The first four alkanes (methane, ethane, propane, and butane) are gases at room temperature and atmospheric pressure. C3-C4. propane and butane are easily liquefied at room temperature under a modest pressure . C5-C8. the next four alkanes are free-flowing, volatile liquids.

1.5 Reaction of alkanes Alkanes are the least reactive class of organic compounds. Their low reactivity is reflected in another term for alkanes:paraffins. The name paraffin comes from two latin terms,para, meaning "opposed to," and affinas, meaning "affinity". Chemists found that alkanes do not react with strong acids or bases , nor with most other reagents. They attributed this low reactivity to a lack of affinity for other reagents, and they coined the name "paraffins."

1.5A combustion At excess of oxygen

At littel amount of oxygen

6CH4 CH4 + + O2 H2O 2CH CO + CH 3H2 + 2CO +10H2O

1.5B Cracking and hydrocracking Catalytic hydrocracking (H2 ,heat

C12H26

C5H12 C7H16

Catalytic cracking by(heat,catalyst)

C12H26

C5H10 + C7H16

1.5c Halogenation Under the propor condition, alkanes react with halogens (F2, Cl2, Br2, I 2) to form alkyl halides.

1.6 Structure and conformations of alkanes. 1.6A structure of methane The simplest alkane is methane, CH4 Methane is perfectly tetrahedral . with the 109.5 bond angles predicted for an sp3 hybrid carbon. The four hydrogen atoms are covalently bonded to centralcarbon atom, with bond lengths of 1.o9A .

C H H H H

C H H H

C H H H

C H H

1.6B Conformationof ethane Ethane,the two-carbone alkanes, is composedof two methyl groups with overlapping sp3 hybrid orbitals forming a sigma bong between them.

1.7 Conformations of butane

10

1.8 Cyclohexane conformations Chair and boat conformations

11

Chapter two The study of chemical reaction

2.1 The chlorination of Methane
Heat or X2
R X

Light

HX

2.2 The Free-Radical chain Reaction

A-The initiation step: B- The propagation steps: C-Termination Reactions:

12

13

2.3 Free-Radical stabilities: The energy required to form a free radical by breaking a bond between a hydrogen atom and carbon atom. This energy is greatest for a methyl carbon. And it decreases for a primary carbon, a secondary carbon, and a tertiary carbon. The more highly substituted the carbon atom, the less energy is required to form the free radical.

R3-C.>R2-CH.>R-CH2.>H3-C. 3>2>1>Me

14