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Hydrocarbons
Aliphatic
Aromatic
Hydrocarbons
Aliphatic
Aromatic
Alkanes
Alkenes
Alkynes
Hydrocarbons
Aliphatic
Alkanes are hydrocarbons in which all of the bonds are single bonds.
H
Alkanes H
H C H
C
H
Hydrocarbons
Aliphatic
H Alkenes
H C C
Hydrocarbons
Aliphatic
Alkynes HC
CH
Hydrocarbons
The most common aromatic hydrocarbons are those that contain a benzene ring. H H H H H H
Aromatic
Functional Group
a structural unit in a molecule responsible for its characteristic chemical behavior and its spectroscopic characteristics
Alkanes RH
RX
Alkanes RH
RX
H
C H
H C Cl + HCl
Families of organic compounds and their functional groups Alcohols Alkyl halides Amines ROH RX (X = F, Cl, Br, I) primary amine: RNH2 secondary amine: R2NH tertiary amine: R3N Ethers ROR
O C Carbonyl group R
O C
Acyl group
O C Carbonyl group R
O C
Aldehyde
O C Carbonyl group R
O C Ketone
R'
O C Carbonyl group R
O C
OH
Carboxylic acid
O C Carbonyl group R
O C Ester
OR'
O C Carbonyl group R
O C Amide
NH2
CnH2n+2
Introduction to Alkanes: Methane, CH4 Ethane, C2H6 Propane, C3H8
The simplest alkanes Methane (CH4) Ethane (C2H6) Propane (C3H8) CH4 CH3CH3 CH3CH2CH3
bp -160C
bp -89C
bp -42C
C4H10
General formula for any butane
n-Butane CH3CH2CH2CH3
C4H10
Isobutane (CH3)3CH
bp -0.4C
bp -10.2C
CnH2n+2
n>4
CH3CH2CH2CH2CH3 n-Pentane
CnH2n+2
n>4
CH3CH2CH2CH2CH2CH3 n-Hexane
CH3CH2CH2CH2CH2CH2CH3 n-Heptane
C5H12
CH3CH2CH2CH2CH3 n-Pentane
(CH3)2CHCH2CH3
Isopentane
(CH3)4C Neopentane
The number of isomeric alkanes increases as the number of carbons increase. There is no simple way to predict how many isomers there are for a particular molecular formula.
1 1 1 2 3 5 9
1 1 1 2 3 5 9
C6H6 Isomers
How many isomers with the composition C6H6 can you draw?
Structure of Ethylene
bond angles: H-C-H = 117 H-C-C = 121 bond distances: CH = 110 pm C=C = 134 pm
planar
Bonding in Ethylene
s s
s s
Bonding in Ethylene
Bonding in Ethylene
Isomerism in Alkenes
Isomers
Isomers are different compounds that have the same molecular formula (composition).
Isomers
Constitutional isomers
Stereoisomers
Isomers
Constitutional isomers
Stereoisomers
same connectivity; different arrangement of atoms in space
different connectivity
Isomers
Constitutional isomers
Stereoisomers
H C H 1-Butene C
CH2CH3
H3C C C
H3C
2-Methylpropene
H3C C
H C
CH3
H3C C
C
CH3
cis-2-Butene
trans-2-Butene
H C H 1-Butene C
CH2CH3
H3C C C
H3C
2-Methylpropene
H3C C
H C
CH3
Constitutional isomers H
cis-2-Butene
H C H 1-Butene C
CH2CH3
H3C C C
H3C
2-Methylpropene H3C H C H
Constitutional isomers
C
CH3
trans-2-Butene
Stereoisomers
H3C C
H C
CH3
H3C C
C
CH3
cis-2-Butene
trans-2-Butene
Chirality
A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable.
Bromochlorofluoromethane is chiral
Cl Br H F
Bromochlorofluoromethane is chiral
Cl Br H F H
Cl Br
F
To show nonsuperposability, rotate this model 180 around a vertical axis.
Bromochlorofluoromethane is chiral
Cl Br H F Cl
Br
H
Another look
Enantiomers
and
Isomers
constitutional isomers
stereoisomers
Isomers
constitutional isomers
stereoisomers
enantiomers (optical)
Chlorodifluoromethane is achiral
Chlorodifluoromethane is achiral
The two structures are mirror images, but are not enantiomers, because they can be superposed on each other.
Plane of symmetry
A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry.
Plane of symmetry
A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry.
Plane of symmetry
A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane of symmetry.
Plane of symmetry
A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane of symmetry.
Boiling Points increase with increasing number of carbons more atoms, more electrons, more opportunities for induced dipole-induced dipole forces decrease with chain branching branched molecules are more compact with smaller surface areafewer points of contact with other molecules
Boiling Points
increase with increasing number of carbons more atoms, more electrons, more opportunities for induced dipole-induced dipole forces
Heptane bp 98C
Octane bp 125C
Nonane bp 150C
branched molecules are more compact with smaller surface areafewer points of contact with other molecules
Octane: bp 125C 2-Methylheptane: bp 118C 2,2,3,3-Tetramethylbutane: bp 107C
governed by strength of intermolecular attractive forces alkanes are nonpolar, so dipole-dipole and dipole-induced dipole forces are absent only forces of intermolecular attraction are induced dipole-induced dipole forces
two nonpolar molecules center of positive charge and center of negative charge coincide in each
temporary dipole in one molecule (left) induces a complementary dipole in other molecule (right)
temporary dipole in one molecule (left) induces a complementary dipole in other molecule (right)
Straight chain hydrocarbon Branched hydrocarbon Lots of intermolecular contacts Fewer intermolecular contacts