Hydrocarbons Lecture no.

29-32

Organic Compounds
Contain carbon Have covalent bonds Have low melting points Have low boiling points Burn in air (oxygen) Generally soluble in nonpolar solvents Form large molecules

Common Elements in Organic Compounds

24.1

Classification of organic compounds:

Classes of organic compounds could be distiguished according to the functional group that the compound contains. A functional group is a group of atoms that is largely responsible for the chemical behavior of the parent molecule.

Most organic compounds are derived from hydrocarbons.

On the basis of structure hydrocarbons are divided into two main classes- aliphatic and aromatic. Aliphatic hydrocarbons are further divided into: alkanes, alkenes, alkynes and cycloalkanes.

Classification of Hydrocarbons

24.1

Alkanes
Contain C

and H only

Contain
Have Are

single bonds C-C

4 bonds to every carbon (C) atom

nonpolar

Alkanes
Alkanes have the general formula CnH2n+2 where n = 1,2,3, only single covalent bonds

saturated hydrocarbons because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule

CH4 methane

C2H6 ethane

C3H8 propane

24.2

Structural isomers are molecules that have the same molecular formula but different structures

24.2

How many structural isomers does pentane, C5H12, have?

H H C H H C H H C H H C H H C H H H H C H CH3 H C H C H H C H
24.2

H H C H H CH3 H C C H

n-pentane

CH3 H

2,2-dimethylpropane

2-methylbutane

Isomers could only be distinguished by their systematic names or IUPAC nomenclature. Decan has 75 isomers.

Alkane Nomenclature
1. The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule. CH3 CH3
1

CH2
2

CH2
3

CH
4

CH2
5

CH2
6

CH3
7

4-methylheptane

2. An alkane less one hydrogen atom is an alkyl group. CH4 CH3

24.2

methane methyl

Alkane Nomenclature
3. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches. CH3 CH3
1

CH
2

CH2
3

CH2
4

CH3
5

2-methylpentane
CH3
1

CH3

CH2
2

CH2
3

CH
4

CH3
5

4-methylpentane
24.2

Alkane Nomenclature
4. Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind. CH3 CH3
1

CH3
CH
3

CH
2

CH2
4

CH2
5

CH3
6

2,3-dimethylhexane
CH3

CH3
1

CH
2

C
3

CH2
4

CH2
5

CH3
6

CH3 3,3-dimethylhexane
24.2

Alkane Nomenclature
5. Use previous rules for other types of substituents. Br CH3
1

NO2
CH
3

CH
2

CH3
4

2-bromo-3-nitrobutane
Br NO2 CH2
2

CH2
1

CH
3

CH3
4

1-bromo-3-nitrobutane
24.2

What is the IUPAC name of the following compound?

CH3 C2H5 CH2
3

CH3
1

CH
2

CH
4

CH2
5

CH2
6

CH2
7

CH3
8

4-ethyl-2-methyloctane

What is the structure of 2-ethyl-4-methylhexane?

C2H5 CH3 CH2
3

CH3
1

CH
2

CH
4

CH2
5

CH3
6

24.2

As low number as possible

Sum of the numbers should be minimum

achiral

chiral
24.2

Optical isomerism in alkanes

Cycloalkanes
Alkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula CnH2n where n = 3,4,

24.2

Cycloalkanes

24.2

Alkenes
Alkenes have the general formula CnH2n where n = 2,3, contain at least one carbon-carbon double bond

also called olefins

CH2 CH CH2 CH3 CH3 CH CH CH3

1-butene
Cl C H C H H Cl Cl

2-butene
H C C Cl

cis-dichloroethylene

trans-dichloroethylene
24.2

prepared by Dr. Harpreet Kaur

Nomenclature of alkene:

Cis-trans isomerism

Cis-Trans Isomerization in the Vision Process

24.2

Alkynes
Alkynes have the general formula CnH2n-2 where n = 2,3,4, contain at least one carbon-carbon triple bond CH C CH2 CH3 CH3 C C CH3

1-butyne Production of acetylene CaC2 (s) + 2H2O (l)

2-butyne

C2H2 (g) + Ca(OH)2 (aq)

24.2

sp

Reactions of alkanes: glance over types of reactions

Alkanes are generally considered unreactive, but under favorable conditions they do react

Alkane Reactions
Combustion
CH4 (g) + 2O2 (g) Halogenation CH4 (g) + Cl2 (g) Cl2 + energy
light

CO2 (g) + 2H2O (l) DH0 = -890.4 kJ

CH3Cl (g) + HCl (g)

Cl + Cl

H
Cl + H C H H H C + Cl Cl H

H
C

H + HCl

H H H C Cl + Cl
24.2

Cracking(prepration of alkenes)
C2H6 (g)
Pt
catalyst

CH2

CH2 (g) + H2 (g)

Reactions of alkenes

Weak electrons are attracted by electrophile and than end of reaction is carried out by nucleophile

Markovnikovs rule: the hydrogen adds to sp2 carbon that is bonded to greater no of hydrogens

prepared by Dr. Harpreet Kaur

Alkene Reactions
Addition Reactions

CH2
CH2

CH2 (g) + HBr (g)

CH2 (g) + Br2 (g)

CH3
CH2Br

CH2Br (g)
CH2Br (g)

24.2

Alkyne Reactions
Hydrogenation CH CH (g) + H2 (g) CH2 CH2 (g)

Addition Reactions CH CH CH (g) + HBr (g) CH (g) + Br2 (g) CH2 CHBr CHBr (g) CHBr (g)

CH

CH (g) + 2Br2 (g)

CHBr2

CHBr2 (g)

24.2

Alkyne Reductions
xs H2 Pt H 3C C C CH 3 H 2 /Pd/BaSO
4

CH 3 CH 2 CH 2 CH 3

H 3C C C H

CH 3 H

Quinoline (Lindlar's Catalys t) Na NH 3 (liq) H 3C C C H H

CH 3

Hydrogen Halide Addition to Alkynes

Heteroatom stabilized carbocation intermediates
H H 3C C C H HX H 3C C C H + XH H 3C C C H Mark ovnikov addition X a vinyl halide X H H 3C C C H

H H 3C C X C H HX H 3C

+ C

H C H

X H

X H a geminal dih alide

H H 3C C C H

X H + a hetero ato m prepared by Dr. Harpreet Kaur stabilized carbocation

Halogenation of Alkynes
Formation of Vicinal tetrahalides
X X C C X X

C C an alk yne

X2 carbon te trachloride

a vicinal tetrahalide

Substitution
R C CH Na R + C C Na

H2

Terminal Alkyne R

+ C C Na + R'CH 2 X
Methyl or Primary Alkyl Halide

C C CH 2R' + NaX

Alkynyl Anion Synthesis of Alkynes via Bimolecular Nucleophilic Substitution

Diels-Alder Reaction
C C C C C C

Six-membered Ring formation (4+2) Diene + Dienophile

Examples of reactions in Alkynes

prepared by Dr. Harpreet Kaur

Chemistry In Action: Ice That Burns