Chapter 24 From Petroleum to Pharmaceuticals
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1 hapter 24 From Petroleum to Pharmaceuticals 24.1 Petroleum Refining and the ydrocarbons 24.2 Functional Groups and Organic Synthesis 24.3 Pesticides and Pharmaceuticals IR Tutor and Infrared Spectroscopy
2 ydrocarbons Aliphatic Aromatic
3 ydrocarbons Aliphatic Aromatic Alkanes Alkenes Alkynes
4 ydrocarbons Aliphatic Alkanes are hydrocarbons in which all of the bonds are single bonds. Alkanes
5 ydrocarbons Aliphatic Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. Alkenes
6 ydrocarbons Aliphatic Alkynes are hydrocarbons that contain a carbon- carbon triple bond. Alkynes
7 ydrocarbons The most common aromatic hydrocarbons are those that contain a benzene ring. Aromatic
8 Reactive Sites in ydrocarbons The Functional Group oncept
9 Functional Group a structural unit in a molecule responsible for its characteristic chemical behavior and its IR spectroscopic characteristics
10 Alkanes R R X 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
11 R Alkanes functional group is a hydrogen R X the reaction that takes place is substitution one of the hydrogens is substituted by some other atom or group + l 2 l + l
12 Functional Groups in ydrocarbons alkanes R alkenes R, double bond alkynes R, triple bond aromatics Ar,, double bond
13 Some Key Functional Groups
14
15 Families of organic compounds and their functional groups Alcohols RO Alkyl halides RX (X = F, l,, Br, I) Amines primary amine: RN 2 secondary amine: R 2 N tertiary amine: R 3 N Ethers ROR
16 Many classes of organic compounds contain a carbonyl group O R O arbonyl group Acyl group
17 Many classes of organic compounds contain a carbonyl group O O R arbonyl group Aldehyde
18 Many classes of organic compounds contain a carbonyl group O O R R' arbonyl group Ketone
19 Many classes of organic compounds contain a carbonyl group O O R O arbonyl group arboxylic acid Not a ketone-alcohol!
20 Many classes of organic compounds contain a carbonyl group O O R OR' arbonyl group Ester Not a ketone-ether!
21 Many classes of organic compounds contain a carbonyl group O O R N 2 arbonyl group Amide Note a ketone-amine!
22 Alkanes General formula for an alkane n 2n+2 Introduction to Alkanes: Methane, 4 Ethane, 2 6 Propane, 3 8
23 The simplest alkanes Methane ( 4 ) Ethane ( 2 6 ) Propane ( 3 8 ) bp -160 bp -89 bp -42 No isomers possible for 1, 2, 3 hydrocarbons
24 Isomeric Alkanes: The Butanes 4 10 General formula for any butane Isomers: same composition, different structures at the constitutional or stereochemical levels
25 4 10 n-butane (bp -0.4 ) Isobutane (bp ( 3 ) 3 bp )
26 igher n-alkanes Pentane ( 5 12 ) and Beyond n 2n+2 n > 4
27 n-pentane n 2n+2 n > n-exane n-eptane
28 The 5 12 Isomers
29 n-pentane ( 3 ) Isopentane ( 3 ) 4 Neopentane
30 ow 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.
31 Table 2.3 Number of onstitutionally Isomeric Alkanes
32 Table 2.3 Number of onstitutionally Isomeric Alkanes , , ,491,178,805,831 (~6 x isomers!)
33 6 6 Isomers ow many isomers with the composition 6 6 can you draw?
34 6 6 Isomers: ow many isomers with the composition 6 6 can you draw?
35 Structure and Bonding in Alkenes
36 Structure of Ethylene bond angles: -- = = 121 bond distances: = 110 pm = = 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 = bond
40 Isomerism in Alkenes
41 Isomers 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 Isomers onstitutional isomers Stereoisomers
43 Isomers onstitutional isomers Stereoisomers different connectivity same connectivity; different arrangement of atoms in space
44 Isomers onstitutional isomers Stereoisomers consider the isomeric alkenes of molecular formula 4 8
45 Butene 2-Methylpropene cis-2-butene trans-2-butene
46 Butene 2-Methylpropene 3 3 onstitutional isomers cis-2-butene
47 Same connections, different atomic positions in space Stereoisomers cis-2-butene trans-2-butene
48 Molecular hirality: Enantiomers
49 Isomers constitutional isomers stereoisomers
50 Isomers constitutional isomers stereoisomers enantiomers (optical) geometric isomers (cis/trans) hiral structures
51 hirality 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.
52 Bromochlorofluoromethane is chiral Br l It cannot be superposed point for point on its mirror image. F
53 Bromochlorofluoromethane is chiral Br l l Br F F To show nonsuperposability, rotate this model 180 around a vertical axis.
54 Bromochlorofluoromethane is chiral Br l l Br F F
55 Another look
56 Enantiomers nonsuperposable mirror images are called enantiomers and are enantiomers with respect to each other
57 hlorodifluoromethane is achiral
58 hlorodifluoromethane is achiral The two structures are mirror images, but are not enantiomers, because they can be superposed on each other.
59 Symmetry in Achiral Structures
60 Symmetry tests for achiral structures Any molecule with a plane of symmetry must be achiral.
61 Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. hlorodifluoromethane has a plane of symmetry.
62 Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. hlorodifluoromethane has a plane of symmetry.
63 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.
64 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.
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hain isomerism Position isomerism Metamerism Tautomerism Functional group isomerism Geometrical isomerism Optical isomerism 02/07/2017 Isomerism The presence of two or more compounds which has the same
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