Lecture 10. More Aromatics. February 18, Chemistry 328N
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1 Lecture 10 More Aromatics February 18, 2016
2 eterocyclic Aromatic Compounds N N O S Pyridine Pyrrole Furan Thiophene
3 ückel and Pyridine
4 ückel and Pyrrole
5 uckel and Furan
6 Recognizing Aromatic Compounds Be careful with uckel s Rule
7 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 21.3!
8 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
9 IR
10 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
11 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-)
12 C 3 C cm -1 C 3 C cm cm -1 C 3 C cm -
13 Ring Current in Benzene Circulating electrons Deshielded B o Secondary magnetic field generated by circulating electrons deshields aromatic protons
14 NMR Spectrum of Toluene 5 C 3 3
15 [18]Annulene 18 electrons satisfies ückel's rule resonance energy = 418 kj/mol bond distances range between pm
16 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
17 Coupling Constants - Aromatics Ortho s = 9 z Meta s = 3 z Para s < 1 z
18 NMR Spectrum of 1-iodo-4-methoxybenzene 3 I OC CCl 3 impurity
19 NMR Spectrum of 1-bromo-4-ethoxybenzene 4 Br OC 2 C 3 3 2
20 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
21 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
22 Carbolic Acid Antiseptic
23 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)
24 Acidity of Phenols Phenols are much more acidic than aliphatic alcohols that also contain the -O group Phenol: pk a = 9.95 O+ 2O O - + 3O + Ethanol: pk a = 15.9 C3 C2 O + 2O C3 C2 O - + 3O + delocalization of the negative charge by resonance stabilizes the phenoxide ion relative to the alkoxide ion
25 Acidity of Phenols O + O - O O pka 9.95 Strong acid + Strong Weak + base base pka 15.7 Weak acid Strong acids have weak conjugate bases Stabilization of anions leads to weakly conjugate bases!
26 Lets move electrons together!! PLEASE FOLLOW ME STEP BY STEP
27 Acidity of Phenols O + O - O O pka 9.95 Strong acid + Strong Weak + base base pka 15.7 Weak acid Strong acids have weak conjugate bases Stabilization of anions leads to weak/stable conjugate bases!
28 Acidity of Phenols Alkyl and halogen substituents effect acidities by inductive effects alkyl groups are electron-releasing by induction halogens are electron-withdrawing by induction O O O O O C 3 C 3 Phenol m-cresol p-cresol pk a 9.95 pk a pk a Cl m-chloro phenol pk a 8.85 Cl p-chlorophenol pk a 9.18
29 Acidities of Phenols Part of the acid-strengthening effect of -NO 2 is due to its electron-withdrawing inductive effect In addition, -NO 2 substituents in the ortho and para positions help to delocalize the negative charge by Resonance O O O + + N N O O O delocalization of negative charge onto oxygen
30 Acidities of Phenols Nitro groups increase the acidity of phenols by both an electron-withdrawing inductive effect and a resonance effect O O O Phenol pk a 9.95 NO 2 m-nitrophenol pk a 8.28 NO 2 p-nitrophenol pk a 7.15
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Lecture Topics: I. Electrophilic Aromatic Substitution (EAS)
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trends in reactivity based on substitution of the starting iodoarene 5. 1) Pd(OAc) 2, CH 2 CN 2) HCl O Triethylamine
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Hour Examination # 1
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Alcohols, protons α to ketones. Aromatics, Amides. Acids, Aldehydes. Aliphatic. Olefins. ppm TMS
Interpretation of 1 spectra So far we have talked about different NMR techniques and pulse sequences, but we haven t focused seriously on how to analyze the data that we obtain from these experiments.