Download presentation
Presentation is loading. Please wait.
Published byBruno Atkins Modified over 9 years ago
1
24.1 Petroleum Refining and the Hydrocarbons 24.2 Functional Groups and Organic Synthesis 24.3 Pesticides and Pharmaceuticals IR Tutor and Infrared Spectroscopy Chapter 24 From Petroleum to Pharmaceuticals
2
HydrocarbonsHydrocarbons AromaticAromaticAliphaticAliphatic
3
HydrocarbonsHydrocarbons AromaticAromaticAliphaticAliphatic AlkanesAlkanes AlkynesAlkynes AlkenesAlkenes
4
HydrocarbonsHydrocarbons AliphaticAliphatic AlkanesAlkanes Alkanes are hydrocarbons in which all of the bonds are single bonds. C C H H H HHH
5
HydrocarbonsHydrocarbons AliphaticAliphatic AlkenesAlkenes Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. C C H H HH
6
HydrocarbonsHydrocarbons AliphaticAliphatic AlkynesAlkynes Alkynes are hydrocarbons that contain a carbon- carbon triple bond. HCCH
7
HydrocarbonsHydrocarbons AromaticAromatic The most common aromatic hydrocarbons are those that contain a benzene ring. H H H HHH
8
Reactive Sites in Hydrocarbons The Functional Group Concept
9
Functional Group a structural unit in a molecule responsible for its characteristic chemical behavior and its IR spectroscopic characteristics
10
AlkanesAlkanes 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 R—H R—X
11
AlkanesAlkanes functional group is a hydrogen the reaction that takes place is substitution one of the hydrogens is substituted by some other atom or group R—H R—X + Cl 2 C C H H H HHH + HCl C C H Cl H HHH
12
Functional Groups in Hydrocarbons alkanesRH alkenes RH, double bond alkynes RH, triple bond aromaticsArH, double bond
13
Some Key Functional Groups
15
Families of organic compounds and their functional groups AlcoholsROH Alkyl halidesRX (X = F, Cl, Br, I) Aminesprimary amine: RNH 2 secondary amine: R 2 NH secondary amine: R 2 NH tertiary amine: R 3 N tertiary amine: R 3 N EthersROR
16
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Acyl group R
17
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Aldehyde R H
18
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Ketone R R'
19
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Carboxylic acid R OH Not a ketone-alcohol!
20
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Ester R OR' Not a ketone-ether!
21
Many classes of organic compounds contain a carbonyl group O C Carbonyl group O C Amide R NH 2 Note a ketone-amine!
22
Introduction to Alkanes: Methane, CH 4 Ethane, C 2 H 6 Ethane, C 2 H 6 Propane, C 3 H 8 C n H 2n+2 General formula for an alkane Alkanes
23
The simplest alkanes Methane (CH 4 ) CH 4 Ethane (C 2 H 6 )CH 3 CH 3 Propane (C 3 H 8 )CH 3 CH 2 CH 3 bp -160°C bp -89°C bp -42°C No isomers possible for C1, C2, C 3 hydrocarbons
24
Isomeric Alkanes: The Butanes C 4 H 10 General formula for any butane Isomers: same composition, different structures at the constitutional or stereochemical levels
25
n-Butane (bp -0.4°C) Isobutane ( bp -10.2°C ) CH 3 CH 2 CH 2 CH 3 (CH 3 ) 3 CH C 4 H 10
26
Higher n-Alkanes Pentane (C 5 H 12 ) and Beyond C n H 2n+2 n > 4
27
CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 n-Pentane n-Hexane CH 3 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 n-Heptane C n H 2n+2 n > 4
28
The C 5 H 12 Isomers
29
n-Pentane CH 3 CH 2 CH 2 CH 2 CH 3 Isopentane (CH 3 ) 2 CHCH 2 CH 3 Neopentane (CH 3 ) 4 C C 5 H 12
30
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. How many isomers?
31
Table 2.3 Number of Constitutionally Isomeric Alkanes CH 4 1 C 2 H 6 1 C 3 H 8 1 C 4 H 10 2 C 5 H 12 3 C 6 H 14 5 C 7 H 16 9
32
Table 2.3 Number of Constitutionally Isomeric Alkanes CH 4 1 C 8 H 18 18 C 2 H 6 1 C 9 H 20 35 C 3 H 8 1 C 10 H 22 75 C 4 H 10 2 C 15 H 32 4,347 C 5 H 12 3 C 20 H 42 366,319 C 6 H 14 5 C 40 H 82 62,491,178,805,831 C 7 H 16 9 (~6 x 10 13 isomers!)
33
C 6 H 6 Isomers How many isomers with the composition C 6 H 6 can you draw?
34
C 6 H 6 Isomers: How many isomers with the composition C 6 H 6 can you draw?
35
Structure and Bonding in Alkenes
36
Structure of Ethylene bond angles: H-C-H = 117° H-C-C = 121° bond distances: C—H = 110 pm C=C = 134 pm planar
37
Bonding in Ethylene Framework of bonds Each carbon is sp 2 hybridized
38
Bonding in Ethylene Each carbon has a half-filled p orbital
39
Bonding in Ethylene Side-by-side overlap of half-filled p orbitals gives a bond which makes it very difficult to rotate about the C=C bond
40
Isomerism in Alkenes
41
IsomersIsomers Isomers are different compounds that have the same composition (numbers and kinds. of atoms). Since the compounds are different, they must have different structures in the way the atoms are connected or arranged in space
42
IsomersIsomers StereoisomersStereoisomers Constitutional isomers
43
IsomersIsomers StereoisomersStereoisomers different connectivity same connectivity; different arrangement of atoms in space
44
IsomersIsomers StereoisomersStereoisomers Constitutional isomers consider the isomeric alkenes of molecular formula C 4 H 8
45
2-Methylpropene 1-Butene cis-2-Butene trans-2-Butene C CHH H CH 2 CH 3 H3CH3CH3CH3C C C CH 3 HH H C C H3CH3CH3CH3CH C C H H H3CH3CH3CH3C H3CH3CH3CH3C
46
2-Methylpropene 1-Butene cis-2-Butene C CHH H CH 2 CH 3 H CH 3 C C H3CH3CH3CH3CH C C H H H3CH3CH3CH3C H3CH3CH3CH3C Constitutional isomers
47
cis-2-Butene trans-2-Butene H3CH3CH3CH3C C C CH 3 HH H C C H3CH3CH3CH3CH Stereoisomers Same connections, different atomic positions in space
48
Molecular Chirality: Enantiomers
49
stereoisomers constitutionalisomers Isomers
50
stereoisomers constitutionalisomers geometric isomers (cis/trans)enantiomers(optical) Isomers Chiral structures
51
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. ChiralityChirality
52
Br Cl H F It cannot be superposed point for point on its mirror image. Bromochlorofluoromethane is chiral
53
Br Cl H F H Cl Br F To show nonsuperposability, rotate this model 180° around a vertical axis. Bromochlorofluoromethane is chiral
54
Br Cl H F H Cl Br F
55
Another look
56
are enantiomers with respect to each other and nonsuperposable mirror images are called enantiomers EnantiomersEnantiomers
57
Chlorodifluoromethane is achiral
58
The two structures are mirror images, but are not enantiomers, because they can be superposed on each other. Chlorodifluoromethane is achiral
59
Symmetry in Achiral Structures
60
Symmetry tests for achiral structures Any molecule with a plane of symmetry must be achiral.
61
A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry
62
A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry
63
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
64
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
Similar presentations
© 2025 SlidePlayer.com. Inc.
All rights reserved.