Chapter 16. Aromatic Compounds
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1 Chapter 16 Aromatic Compounds
2 Discovery of Benzene Isolated in 1825 by Michael Faraday who determined C:H ratio to be 1:1. Synthesized in 1834 by Eilhard Mitscherlich who determined molecular formula to be C 6 H 6. He named it benzin. Other related compounds with low C:H ratios had a pleasant smell, so they were classified as aromatic. Chapter 16 2
3 Kekulé Structure Proposed in 1866 by Friedrich Kekulé, shortly after multiple bonds were suggested. Failed to explain existence of only one isomer of 1,2-dichlorobenzene. H H H C H C C C C C H H Chapter 16 3
4 Resonance Structures of Benzene Benzene is actually a resonance hybrid between the two Kekulé structures. The C C bond lengths in benzene are shorter than typical single-bond lengths, yet longer than typical double-bond lengths (bond order 1.5). Benzene's resonance can be represented by drawing a circle inside the six-membered ring as a combined representation. Chapter 16 4
5 Structure of Benzene Each sp 2 hybridized C in the ring has an unhybridized p orbital perpendicular to the ring which overlaps around the ring. The six pi electrons are delocalized over the six carbons. Chapter 16 5
6 Unusual Addition of Bromine to Benzene When bromine adds to benzene, a catalyst such as FeBr 3 is needed. The reaction that occurs is the substitution of a hydrogen by bromine. Addition of Br 2 to the double bond is not observed. Chapter 16 6
7 Resonance Energy Benzene does not have the predicted heat of hydrogenation of -359 kj/mol. The observed heat of hydrogenation is -208 kj/mol, a difference of 151 kj. This difference between the predicted and the observed value is called the resonance energy. Chapter 16 7
8 Molar Heats of Hydrogenation Chapter 16 8
9 Annulenes Annulenes are hydrocarbons with alternating single and double bonds. Benzene is a six-membered annulene, so it can be named [6]-annulene. Cylobutadiene is [4]-annulene, cyclooctatetraene is [8]-annulene. Chapter 16 9
10 Annulenes All cyclic conjugated hydrocarbons were proposed to be aromatic. However, cyclobutadiene is so reactive that it dimerizes before it can be isolated. Cyclooctatetraene adds Br 2 readily to the double bonds. Molecular orbitals can explain aromaticity. Chapter 16 10
11 MO Rules for Benzene Six overlapping p orbitals must form six molecular orbitals. Three will be bonding, three antibonding. Lowest energy MO will have all bonding interactions, no nodes. As energy of MO increases, the number of nodes increases. Chapter 16 11
12 MO s for Benzene Highest molecular orbital Lowest molecular orbital Chapter 16 12
13 First MO of Benzene The first MO of benzene is entirely bonding with no nodes. It has very low energy because it has six bonding interactions and the electrons are delocalized over all six carbon atoms. Chapter 16 13
14 Intermediate MO of Benzene The intermediate levels are degenerate (equal in energy) with two orbitals at each energy level. Both π 2 and π 3 have one nodal plane. Chapter 16 14
15 All Antibonding MO of Benzene The all-antibonding π 6 * has three nodal planes. Each pair of adjacent p orbitals is out of phase and interacts destructively. Chapter 16 15
16 Energy Diagram for Benzene The six electrons fill three bonding pi orbitals. All bonding orbitals are filled ( closed shell ), an extremely stable arrangement. Chapter 16 16
17 Aromatic Requirements Structure must be cyclic with conjugated pi bonds. Each atom in the ring must have an unhybridized p orbital (sp 2 or sp). The p orbitals must overlap continuously around the ring. Structure must be planar (or close to planar for effective overlap to occur) Delocalization of the pi electrons over the ring must lower the electronic energy. Chapter 16 17
18 Anti- and Nonaromatic Antiaromatic compounds are cyclic, conjugated, with overlapping p orbitals around the ring, but electron delocalization increases its electronic energy. Nonaromatic compounds do not have a continuous ring of overlapping p orbitals and may be nonplanar. Chapter 16 18
19 Hückel s Rule Once the aromatic criteria is met, Huckel s rule applies. If the number of pi electrons is (4N + 2) the compound is aromatic (where N is an integer) If the number of pi electrons is (4N) the compound is antiaromatic. Chapter 16 19
20 Naphthalene Fused rings share 2 atoms and the bond between them. Naphthalene is the simplest fused aromatic hydrocarbon. Chapter 16 20
21 Fused Ring Hydrocarbons Chapter 16 21
22 Polynuclear Aromatic Hydrocarbons H B r B r H B r H B r H As the number of aromatic rings increases, the resonance energy per ring decreases, so larger polynuclear aromatic hydrocarbons will add Br 2. Chapter 16 22
23 Larger Polynuclear Aromatic Hydrocarbons Formed in combustion (tobacco smoke). Many are carcinogenic. Epoxides form, combine with DNA base. pyrene Chapter 16 23
24 Allotropes of Carbon Amorphous: small particles of graphite; charcoal, soot, coal, carbon black. Diamond: a lattice of tetrahedral C s. Graphite: layers of fused aromatic rings Chapter 16 24
25 Some New Allotropes Fullerenes: 5- and 6-membered rings arranged to form a soccer ball structure. Nanotubes: half of a C 60 sphere fused to a cylinder of fused aromatic rings. Chapter 16 25
26 Fused Heterocyclic Compounds Common in nature, synthesized for drugs. Chapter 16 26
27 Common Names of Benzene Derivatives Chapter 16 27
28 Disubstituted Benzenes Numbers can also be used to identify the relationship between the groups; ortho- is 1,2-disubstituted, meta- is 1,3, and para- is 1,4. Chapter 16 28
29 Three or More Substituents Use the smallest possible numbers, but the carbon with a functional group is #1. Chapter 16 29
30 Common Names for Disubstituted Benzenes C H 3 C H 3 O C O H C H 3 O H C H 3 H 3 C C H 3 H 3 C m -xylene mesitylene o -toluic acid p -cresol Chapter 16 30
31 Phenyl and Benzyl B r C H 2 B r phenyl bromide benzyl bromide Phenyl indicates the benzene ring attachment. The benzyl group has an additional carbon. Chapter 16 31
32 Physical Properties of Aromatic Compounds Melting points: More symmetrical than corresponding alkane, pack better into crystals, so higher melting points. Boiling points: Dependent on dipole moment, so ortho > meta > para, for disubstituted benzenes. Density: More dense than nonaromatics, less dense than water. Solubility: Generally insoluble in water. Chapter 16 32
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