18.1 Intro to Aromatic Compounds
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1 18.1 Intro to Aromatic Compounds AROMATIC compounds or ARENES include benzene and benzene derivatives. Aromatic compounds are quite common. Many aromatic compounds were originally isolated from fragrant oils. However, many aromatic compounds are odorless. Klein, Organic Chemistry 1e 18-1
2 8 of the 10 best-selling drugs have aromatic moieties. Klein, Organic Chemistry 1e 18-2
3 Coal contains aromatic rings fused together and joined by nonromantic moieties. Klein, Organic Chemistry 1e 18-3
4 18.2 Nomenclature of Benzene Derivatives Benzene is generally the parent name for monosubstituted derivatives. Klein, Organic Chemistry 1e 18-4
5 Many benzene derivatives have common names that become the parent name. (memorize these) Klein, Organic Chemistry 1e 18-5
6 If the substituent is larger than the ring, the substituent becomes the parent chain. Aromatic rings are often represented with a Ph (for phenyl) or with a φ (phi) symbol. Klein, Organic Chemistry 1e 18-6
7 The common name for dimethyl benzene derivatives is XYLENE. What do ORTHO, META, and PARA mean? Klein, Organic Chemistry 1e 18-7
8 Locants are required for rings with more than 2 substituents. 1. Identify the parent chain (generally the aromatic ring): Often a common name can be the parent chain. 2. Identify and name the substituents. Klein, Organic Chemistry 1e 18-8
9 3. Number the parent chain A substituent that is part of the parent name must be assigned locant NUMBER List the numbered substituents before the parent name in alphabetical order: Ignore prefixes (except iso) when ordering alphabetically. Complete the name for the molecule above. Klein, Organic Chemistry 1e 18-9
10 Section: 18.2 What is the correct name for the following? NH 2 Br a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene d. all of the above Klein, Organic Chemistry 1e
11 18.3 Structure of Benzene In 1866, August Kekulé proposed that benzene is a ring comprised of alternating double and single bonds. Kekulé suggested that the exchange of double and single bonds was an equilibrium process. Klein, Organic Chemistry 1e 18-11
12 We now know that the aromatic structures are resonance contributors rather than in equilibrium. Sometimes the ring is represented with a circle in it Klein, Organic Chemistry 1e 18-12
13 18.4 Stability of Benzene The stability that results from a ring being aromatic is striking. Recall that in general, alkenes readily undergo addition reactions. Aromatic rings are stable enough that they do not undergo such reactions. Klein, Organic Chemistry 1e 18-13
14 Heats of hydrogenation can be used to quantify aromatic stability. Klein, Organic Chemistry 1e 18-14
15 Molecular orbital (MO) theory can help us explain aromatic stability. The six atomic p-orbitals of benzene overlap to make six MOs. Klein, Organic Chemistry 1e 18-15
16 Summary of Critical Points of MO Theory MO Theory is good for describing excited states, ions, exotic species that defy Lewis structures. Mix n atomic orbitals to form n molecular orbitals each orbital has max occupation = 2 electrons Fill from lowest energy MO An MO has NO EFFECT until it contains an electron For each bonding MO, there exists an anti-bonding MO that can exactly cancel the bonding MO Most likely excitation moves one electron from HOMO to LUMO
17 18.4 Stability of Benzene we can use FROST CIRCLES to predict the relative MO energies. Klein, Organic Chemistry 1e 18-17
18 Use the FROST CIRCLES below to explain the 4n+2 rule. Note that the number of bonding orbitals is always an odd number; aromatic compounds will always have an odd number of electron pairs. Klein, Organic Chemistry 1e 18-18
19 18.5 Aromatic Compounds Other Than Benzene Some rings must carry a formal charge to be aromatic. Consider a 5-membered ring. Klein, Organic Chemistry 1e 18-19
20 The pk a value for cyclopentadiene is much lower than typical C-H bonds. WHY? vs. Klein, Organic Chemistry 1e 18-20
21 Consider a 7-membered ring. If six pi electrons are present, what charge will be necessary? Klein, Organic Chemistry 1e 18-21
22 Which of the following are aromatic? A. B. C. a. A b. B c. C d. A and B e. B and C f. A and C g. none of the above h. all of the above Klein, Organic Chemistry 1e
23 Heteroatoms (atoms other than C or H) can also be part of an aromatic ring. If the heteroatom s lone pair is necessary, it will be included in the HÜCKEL number of pi electrons. Klein, Organic Chemistry 1e 18-23
24 If the lone pair is necessary to make it aromatic, the electrons will not be as basic. pk a =5.2 pk a =0.4 Klein, Organic Chemistry 1e 18-24
25 The difference in electron density can also be observed by viewing the electrostatic potential maps. Klein, Organic Chemistry 1e 18-25
26 Will the compounds below be aromatic, antiaromatic, or non aromatic? Klein, Organic Chemistry 1e 18-26
27 Klein, Organic Chemistry 1e 18-27
28 18.6 Reactions at the Benzylic Position A carbon that is attached to a benzene ring is BENZYLIC. Recall that aromatic rings and alkyl groups are not easily oxidized. Klein, Organic Chemistry 1e 18-28
29 HOWEVER, benzylic positions can readily be fully oxidized. The benzylic position needs to have at least one proton attached to undergo oxidation. Klein, Organic Chemistry 1e 18-29
30 Permanganate can also be used as an oxidizing reagent. Klein, Organic Chemistry 1e 18-30
31 BENZYLIC positions have similar reactivity to allylic positions. Benzylic positions readily undergo free radical bromination. Klein, Organic Chemistry 1e 18-31
32 Once the benzylic position is substituted with a bromine atom, a range of functional group transformations are possible. Klein, Organic Chemistry 1e 18-32
33 Once the benzylic position is substituted with a bromine atom, a range of functional group transformations are possible. Klein, Organic Chemistry 1e 18-33
34 Klein, Organic Chemistry 1e 18-34
35 18.6 Reactions at the Benzylic Position Give necessary reagents for the reactions below. Klein, Organic Chemistry 1e 18-35
36 Section: 18.6 What is the correct order of reagents to achieve the following synthesis? O Br a. 1) CH 3 CH 2 CH 2 MgBr 2) H 2 O b. NBS, light, CCl 4 c. HBr d. NaBr e. 1) LAH 2) H 2 O 1) A 2) E, B 3) E, C 4) E, D 5) E, B, C Klein, Organic Chemistry 1e
37 18.7 Reduction of the Aromatic Moiety Under forceful conditions, benzene can be reduced to cyclohexane. Is the process endothermic or exothermic? WHY? WHY are forceful conditions required? Klein, Organic Chemistry 1e 18-37
38 Vinyl side groups can be selectively reduced. ΔH is just slightly less than the expected 120 kj/mol expected for a C=C C C conversion. WHY are less forceful conditions required? Klein, Organic Chemistry 1e 18-38
39 18.7 Reduction of the Aromatic Moiety Note that the BIRCH reduction product has sp 3 hybridized carbons on opposite ends of the ring. Klein, Organic Chemistry 1e 18-39
40 Like alkenes, benzene can undergo the BIRCH reduction. Klein, Organic Chemistry 1e 18-40
41 Like alkenes, benzene can undergo the BIRCH reduction. Draw the final product. Klein, Organic Chemistry 1e 18-41
42 The presence of an electron donating alkyl side group or EWD groups provides different regioselectivity. Why? Klein, Organic Chemistry 1e 18-42
43 Section: 18.7 What is the product(s) of the following reaction. NO 2 Na, CH 3 OH NH 3 A. C. NO 2 NO 2 B. D. NO 2 NO 2 Klein, Organic Chemistry 1e
44 Section: 18.8 In 1H NMR spectrometry, aromatic C-H bonds show peaks at ppm. In C NMR spectrometry, aromatic carbons show peaks at ppm. In IR spectroscopy, aromatic C-H bonds show peaks at cm 1. a. 3 4, , b , , c. 3 4, , 2250 d , , Klein, Organic Chemistry 1e
45 18.8 Spectroscopy of Aromatic Compounds Klein, Organic Chemistry 1e 18-45
46 IR spectra for ethylbenzene: Klein, Organic Chemistry 1e 18-46
47 NMR of Aromatics Recall from Section 16.5 how the anisotropic effects of an aromatic ring affect NMR shifts. Klein, Organic Chemistry 1e 18-47
48 NMR of Aromatics The integration and splitting of protons in the aromatic region of the 1 H NMR ( 7 ppm) in often very useful. Klein, Organic Chemistry 1e 18-48
49 NMR of Aromatic Compounds Because of possible ring symmetry, the number of signals in the 13 C NMR ( ppm) generally provides structural information. Klein, Organic Chemistry 1e 18-49
50 For the molecule below, predict the shift for the 13 C signals, and predict the shift, integration, and multiplicity for the 1 H NMR signals. Klein, Organic Chemistry 1e 18-50
51 Graphite, Buckyballs, and Nanotubes Graphite consists of layers of sheets of fused aromatic rings. Klein, Organic Chemistry 1e 18-51
52 Buckyballs are C 60 spheres made of interlocking aromatic rings. Fullerenes come in other sizes such as C 70. How are Buckyballs aromatic when they are not FLAT? Klein, Organic Chemistry 1e 18-52
53 Fullerenes can also be made into tubes (cylinders). Single, double, and multi-walled carbon nanotubes have many applications: Conductive Plastics, Energy Storage, Conductive Adhesives, Molecular Electronics, Thermal Materials, Fibres and Fabrics, Catalyst Supports, Biomedical Applications Klein, Organic Chemistry 1e 18-53
Organic Chemistry. Second Edition. Chapter 18 Aromatic Compounds. David Klein. Klein, Organic Chemistry 2e
Organic Chemistry Second Edition David Klein Chapter 18 Aromatic Compounds Copyright 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e 18.1 Introduction to Aromatic Compounds
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