Lecture 10. More Aromatics. February 15, Chemistry 328N
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1 Lecture 10 More Aromatics February 15, 2018
2 ückel's Rule for Aromaticity To be Aromatic a compound must : 1. be Cyclic 2. have one P orbital on each atom in the ring 3. be planar or nearly so to give orbital overlap 4. have a closed loop of 4n+2 pi electrons in the cyclic arrangement of p orbitals
3 ückel's Rule Among planar, monocyclic, completely conjugated polyenes, only those with 4n + 2p electrons possess special stability (are aromatic) n 4n benzene! Magic Numbers
4 ückel's Rule Actually and inadvertently defines a condition for cyclic molecules in which the bonding molecular orbitals are filled and there are no electrons in non-bonding or antibonding orbitals. roughly analogous to the rare gas condition for atomic orbitals
5 p-mos of Benzene Antibonding Benzene 6 p electrons fill all of the bonding orbitals all p antibonding orbitals are empty Bonding
6 p-mos of Cyclooctatetraene Antibonding Nonbonding Cyclooctatetraene Bonding
7 Aromatic Ions Radical Anion p e s Radical Cation Cation Anion
8 Cyclopentadiene Let s fill these for each case, radical, anion and cation p e s Radical Cation Anion
9 Cycloheptatriene Radical Anion p e s Radical Cation Anion Cation
10 Cycloheptatriene Let s fill these for each case, radical, anion and cation p e s Radical Cation Anion
11 Compare Acidities of Cyclopentadiene and Cycloheptatriene pk a = 16 pk a = 36 K a = K a = 10-36
12 Cyclopropenyl Cation + also written as + n = 0 4n +2 = 2 p electrons!!
13 n = 0 (4n+2 = 2) fills a bonding MO
14 Discovery of Cyclopropylium Cation Ron Breslow While still in his twenties, Breslow made two groundbreaking contributions to mechanistic organic chemistry. is synthesis of a cyclopropenyl cation generalized the concept of aromaticity to cyclic systems with only 2 π-electrons. This work was bolstered by showing that cyclopropenyl anions and cyclopentadienyl cations, each with 4n π- electrons in a cyclic array, are antiaromatic (a term Breslow coined).
15 Cyclooctatetraene Dianion also 2 written as n = 2 4n +2 = 10 p electrons
16 eterocyclic Aromatic Compounds
17 eterocyclic Aromatic Compounds N N O S Pyridine Pyrrole Furan Thiophene
18 eterocyclic Aromatic Compounds and ückel's Rule N Pyridine 6 p electrons in ring lone pair on nitrogen is in an sp 2 hybridized orbital; not part of p system of ring
19 ückel and Pyridine
20 N Pyrrole lone pair on nitrogen must be part of ring p system if ring is to have 6 p electrons lone pair must be in a p orbital in order to overlap with ring p system
21 ückel and Pyrrole
22 Furan O two lone pairs on oxygen one pair is in a p orbital and is part of ring p system; other is in an sp 2 hybridized orbital and is not part of ring p system
23 uckel and Furan
24 Recognizing Aromatic Compounds Be careful with uckel s Rule
25 Some Nomenclature A B A A Ortho or 1,2 Meta or 1,3 B B Para or 1,4 Please read about naming in Chapter 21!
26 Some Nomenclature Please read about naming in Chapter Many substituted benzenes are so old and so common that they have been given nick names! O C 3 C 3 C 3 C 3 C 3 C 3 C 3
27 IR
28 Benzene rings--substitution patterns R 750,700 R 750 R 850,780, 700 R R 820 R R Unreliable with NO 2, CO 2 subs From Crewes, Rodriguez and Jaspars, ch 8 Out-of-plane bending combinations, quite small, but in a normally clean region of IR. Reliable even with nitro or carboxyl substitution
29 If the region between cm -1 (w) is free of interference (C=O stretching frequency) a weak grouping of peaks is observed for aromatic systems. Analysis of this region can lead to a determination of the substitution pattern on the aromatic ring G G G G G G G Monosubstituted 1,2 disubstituted (ortho or o-) 1,2 disubstituted (meta or m-) 1,4 disubstituted (para or p-)
30 C 3 C cm -1 C 3 C cm cm -1 C 3 C cm -
31 Ring Current in Benzene Circulating p electrons Deshielded B o Secondary magnetic field generated by circulating p electrons deshields aromatic protons
32
33 NMR Spectrum of Toluene 5 C 3 3
34 [18]Annulene 18 p electrons satisfies ückel's rule resonance energy = 418 kj/mol bond distances range between pm
35 nmr Spectroscopy Ring Current effect is massive in the larger annulenes, for example for [18]annulene the six hydrogens on the inside of the ring resonate at d !! Up field of TMS!! the twelve hydrogens on the outside of the ring resonate at d 9.3
36 Coupling Constants - Aromatics Ortho s = 9 z Meta s = 3 z Para s < 1 z
37 NMR Spectrum of 1-iodo-4-methoxybenzene 3 I OC CCl 3 impurity
38 NMR Spectrum of 1-bromo-4-ethoxybenzene 4 Br OC 2 C 3 3 2
39 TE p-disubstituted PATTERN CANGES AS TE TWO GROUPS BECOME MORE AND MORE SIMILAR All peaks move closer. Outer peaks get smaller.. and finally disappear. Inner peaks get taller. and finally merge. X X X Y X' X all equivalent X = Y X ~ X X = X
40 Phenol Joseph Lister A British surgeon and a pioneer of antiseptic surgery, who successfully introduced carbolic acid (now known as phenol) to sterilize surgical instruments and to clean wounds, which led to reducing post-operative infections and made surgery safer for patients
41 Carbolic Acid Antiseptic
42 Phenols The functional group of a phenol is an -O group bonded to a benzene ring O O Phenol C 3 3-Methylphenol (m-cresol)
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