Ch 24 From Petroleum to Pharmaceuticals Classes of Hydrocarbons

Hydrocarbons

Aliphatic

Aromatic

Hydrocarbons

Aliphatic

Aromatic

Alkanes

Alkenes

Alkynes

Hydrocarbons Aliphatic Alkanes are hydrocarbons in which all of the bonds are single bonds. H H C H H Alkanes H C H .

H Alkenes H C C H H .Hydrocarbons Aliphatic Alkenes are hydrocarbons that contain a carboncarboncarbon double bond.

Hydrocarbons Aliphatic Alkynes are hydrocarbons that contain a carboncarboncarbon triple bond. Alkynes HC CH .

H H H H H H Aromatic .Hydrocarbons The most common aromatic hydrocarbons are those that contain a benzene ring.

Reactive Sites in Hydrocarbons The Functional Group Concept .

Functional Group a structural unit in a molecule responsible for its characteristic chemical behavior and its spectroscopic characteristics .

Alkanes R ²H R ²X functional group is a hydrogen atom the reaction that takes place is termed a substitution one of the hydrogens is substituted by some other atom or group. X .

Alkanes R ²H R ²X functional group is a hydrogen the reaction that takes place is substitution one of the hydrogens is substituted by some other atom or group H H C H H C H H + Cl2 H H C H H C H Cl + HCl .

triple bond ArH. double bond . double bond RH.Functional Groups in Hydrocarbons alkanes alkenes alkynes aromatics RH RH.

Some Key Functional Groups .

I) primary amine: RNH2 secondary amine: R2NH tertiary amine: R3N Ethers ROR . Cl. Br.Families of organic compounds and their functional groups Alcohols Alkyl halides Amines ROH RX (X = F.

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C Acyl group .

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C H Aldehyde .

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C Ketone R' .

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C OH Carboxylic acid .

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C Ester OR' .

Many classes of organic compounds contain a carbonyl group O C Carbonyl group R O C Amide NH2 .

General formula for an alkane CnH2n+2 Introduction to Alkanes: Methane. CH4 Ethane. C3H8 . C2H6 Propane.

The simplest alkanes Methane (CH4) Ethane (C2H6) Propane (C3H8) CH4 CH3CH3 CH3CH2CH3 bp -160°C 160° bp -89°C 89° bp -42°C 42° No isomers possible for C1. C2. C3 hydrocarbons .

Isomeric Alkanes: The Butanes C4H10 General formula for any butane .

2° .n-Butane CH3CH2CH2CH3 C4H10 Isobutane (CH3)3CH bp -0.4° bp -10.4°C 0.2°C 10.

Higher n-Alkanes Pentane (C5H12) and Beyond CnH2n+2 n>4 .

CH3CH2CH2CH2CH3 n-Pentane CnH2n+2 n>4 CH3CH2CH2CH2CH2CH3 n-Hexane CH3CH2CH2CH2CH2CH2CH3 n-Heptane .

The C5H12 Isomers .

C5H12 CH3CH2CH2CH2CH3 n-Pentane (CH3)2CHCH2CH3 Isopentane (CH3)4C Neopentane .

How many isomers? 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.

Table 2.3 Number of Constitutionally Isomeric Alkanes CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 1 1 1 2 3 5 9 .

347 C20H42 366.319 C40H82 62.Table 2.805.491.3 Number of Constitutionally Isomeric Alkanes CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 1 1 1 2 3 5 9 C8H18 18 C9H20 35 C10H22 75 C15H32 4.831 .178.

C6H6 Isomers How many isomers with the composition C6H6 can you draw? .

C6H6 Isomers: How many isomers with the composition C6H6 can you draw? .

Structure and Bonding in Alkenes .

Structure of Ethylene bond angles: H-C-H = 117° 117° H-C-C = 121° 121° bond distances: C²H = 110 pm C=C = 134 pm planar .

Bonding in Ethylene W W W W W Framework of W bonds Each carbon is sp2 hybridized .

Bonding in Ethylene Each carbon has a half-filled p halforbital .

Bonding in Ethylene Side-bySide-by-side overlap of half-filled p halforbitals gives a T bond .

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

consider the isomeric alkenes of molecular formula C4H8

H C H 1-Butene H3 C C H C C CH2CH3 H3 C C C H H H3 C H 2-Methylpropene CH3 H3 C C H H C CH3 H ciscis-2-Butene transtrans-2-Butene .

H C H 1-Butene H3 C C H C C CH2CH3 H3 C C C H H H3 C H 2-Methylpropene CH3 Constitutional isomers H ciscis-2-Butene .

H C H 1-Butene C CH2CH3 H3 C C C H H H3 C H 2-Methylpropene H3 C H C H C CH3 Constitutional isomers transtrans-2-Butene .

Stereoisomers H3 C C H C CH3 H3 C C C H H H CH3 ciscis-2-Butene transtrans-2-Butene .

Molecular Chirality: Enantiomers .

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 It cannot be superposed point for point on its mirror image.

rotate this model 180° 180° around a vertical axis.Bromochlorofluoromethane is chiral Cl Br H F H Cl Br F To show nonsuperposability. .

Bromochlorofluoromethane is chiral Cl Br H F Cl Br H F .

Another look .

Enantiomers nonsuperposable mirror images are called enantiomers and are enantiomers with respect to each other .

Isomers constitutional isomers stereoisomers .

Isomers constitutional isomers stereoisomers enantiomers (optical) geometric isomers (cis/trans) .

Chlorodifluoromethane is achiral .

because they can be superposed on each other. . but are not enantiomers.Chlorodifluoromethane is achiral The two structures are mirror images.

Symmetry in Achiral Structures .

Symmetry tests for achiral structures Any molecule with a plane of symmetry must be achiral. .

Chlorodifluoromethane has a plane of symmetry. .Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves.

Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. .

chloroof 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 Bromo.

Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane Bromo.chloroof symmetry. .

Physical Properties of Alkanes and Cycloalkanes .

Boiling Points increase with increasing number of carbons more atoms. more opportunities for induced dipole-induced dipoledipole forces decrease with chain branching branched molecules are more compact with smaller surface area²fewer points of contact area² with other molecules . more electrons.

.

more electrons. more opportunities for induced dipole-induced dipoledipole forces Heptane bp 98°C 98° Octane bp 125°C 125° Nonane bp 150°C 150° .Boiling Points increase with increasing number of carbons more atoms.

Boiling Points decrease with chain branching branched molecules are more compact with smaller surface area²fewer points of contact area² with other molecules Octane: bp 125°C 125° 2-Methylheptane: bp 118°C 118° 2.2.3107° .3.3.3-Tetramethylbutane: bp 107°C 2.2.

Boiling Points of Alkanes governed by strength of intermolecular attractive forces alkanes are nonpolar. so dipole-dipole and dipoledipoledipole-induced dipole forces are absent only forces of intermolecular attraction are induced dipole-induced dipole forces dipole- .

Induced dipole-Induced dipole attractive forces dipole- + ± ± + two nonpolar molecules center of positive charge and center of negative charge coincide in each .

Induced dipole-Induced dipole attractive forces dipole- + ± ± + movement of electrons creates an instantaneous dipole in one molecule (left) .

Induced dipole-Induced dipole attractive forces dipole- + ± ± + temporary dipole in one molecule (left) induces a complementary dipole in other molecule (right) .

Induced dipole-Induced dipole attractive forces dipole- + ± + ± temporary dipole in one molecule (left) induces a complementary dipole in other molecule (right) .

Induced dipole-Induced dipole attractive forces dipole- + ± + ± the result is a small attractive force between the two molecules .

Induced dipole-Induced dipole attractive forces dipole- ± + ± + the result is a small attractive force between the two molecules .

Straight chain hydrocarbon Branched hydrocarbon Lots of intermolecular contacts Fewer intermolecular contacts .

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