Chapter 21. Phenols and Aryl Halides. Nucleophilic Aromatic Substitution. Ch. 21-1
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1 Chapter 21 Phenols and Aryl alides Nucleophilic Aromatic Substitution Ch. 21-1
2 1. Structure and Nomenclature of Phenols Phenol 1-Naphthol (α-naphthol) 9-Phenanthrol Ch. 21-2
3 1A. Nomenclature of Phenols Cl C 3 N 2 4-Chlorophenol (p-chlorophenol) 2-Nitrophenol (o-nitrophenol) 3-Methylphenol (m-cresol) Ch. 21-3
4 The benzenediols also have common names 1,2-Benzenediol (catechol) 1,3-Benzenediol (resorcinol) 1,4-Benzenediol (hydroquinone) Ch. 21-4
5 2. Naturally ccurring Phenols L-Tyrosine + N 3 C 3 C 2 C 3 Methyl salicylate (oil of wintergreen) C 3 Eugenol (oil of cloves) Estradiol Ch. 21-5
6 3. Physical Properties of Phenols C 3 Phenol Toluene M.W B.P. ( o C) Ch. 21-6
7 4. Synthesis of Phenols 4A. Laboratory Synthesis N 2 N 2 Cu 2, Cu 2+ R N R 2 R e.g. N 2 Cl C 3 1. NaN 2, Cl, 0-5 o C 2. Cu 2, Cu 2+, 2 Cl C 3 Ch. 21-7
8 4B. Industrial Syntheses ydrolysis of chlorobenzene (Dow Process) Cl 2 Na 350 o C high pressure Na + NaCl + 2 Cl + NaCl Ch. 21-8
9 From cumene hydroperoxide + 3 P o C high pressure (Cumene) o C o C (Cumene hydroperoxide) Ch. 21-9
10 Mechanism Chain initiation Step 1 R + R Ch
11 Step 2 Chain propagation + Step Ch
12 Chain propagation Ch
13 5. Reactions of Phenols as Acids pk a pk a N 7.15 N 2 3 C N 3.96 N 2 Cl N 0.38 N 2 Ch
14 pk a (N resonance stabilization) Ch
15 Ch
16 5B. Distinguishing and Separating Question Phenols from Alcohols and Carboxylic Acids If you are given three unknown samples: one is benzoic acid; one is phenol; and one is cyclohexyl alcohol; how would you distinguish them by simple chemical tests? Recall: acidity of > > Ch
17 R + Na R Na (soluble in water) Na Na (soluble in water) + Na No Reaction (immiscible with 2 ) Ch
18 + NaC 3 Na + C 2 (g) + 2 (gas evolved) + NaC3 No Reaction + NaC3 No Reaction Ch
19 6. ther Reactions of the Group of Phenols R R base R R Cl base Ch
20 6A. Phenols in the Williamson Synthesis Na R Na R R R X (X = halides, Ts, Ms) R e.g. 1. Na 2. Br Ch
21 7. Cleavage of Alkyl Aryl Ethers R R conc. X heat R + RX e.g. conc. Cl heat + Cl Ch
22 8. Reactions of the Benzene Ring of Phenols Bromination 3 Br 2 2 Br Br + 3 Br Br (N Lewis acid required for the brominations) Br 2 CS 2, 5 o C + Br Br Ch
23 Nitration 20% N 3 N o C N 2 (30-40%) (15%) Ch
24 Sulfonation conc. 2 S 4 S 3 25 o C conc. 2 S o C conc. 2 S o C S 3 Ch
25 Kolbe reaction Na 1. C 2 C (Salicylic acid) Ch
26 Mechanism Na C C Na tautomerization 3 + Na Salicylic acid Sodium salicylate Ch
27 C R R C 3 C C + (Salicylic acid) Acetylsalicylic acid (Aspirin) Ch
28 9. The Claisen Rearrangement 1. Na 2. Br 200 o C Ch
29 Via a [3,3] sigmatropic rearrangement 2 1 1' 3 2' 3' keto-enol tautomerization Ch
30 10. Quinones - 2 e + 2 e ydroquinone p-benzoquinone Ch
31 3 C C e, C C 3 n - 2 e, Ubiquinones (n = 6-10) (coenzymes Q) 3 C C 3 3 C C 3 Ubiquinol (hydroquinone form) n Ch
32 1,4-Naphthoquinone C 3 3 Vitamin K 1 Ch
33 11. Aryl alides and Nucleophilic Aromatic Substitution Cl 2 + Na N substitution heat Cl 2 + Na N substitution heat X Nu: X N reaction Ch
34 X X X X X Ch
35 11A. Nucleophilic Aromatic Substitution by Addition Elimination: The S N Ar Mechanism Nucleophilic aromatic substitution can occur when strong electron-withdrawing groups are ortho or para to the halogen atom Cl N 2 + aq. NaC o C 3 + N 2 Ch
36 Cl N 2 + aq. NaC o C 3 + N 2 N 2 N 2 Cl 2 N N 2 + aq. NaC o C N N N 2 N 2 Ch
37 The mechanism that operates in these reactions is an addition elimination mechanism involving the formation of a carbanion with delocalized electrons, called a Meisenheimer intermediate. The process is called nucleophilic aromatic substitution (S N Ar) Ch
38 The S N Ar mechanism Cl Cl N 2 + addition slow N 2 elimination fast + Cl + N 2 N 2 Ch
39 Cl Cl Cl N N N Cl N Ch
40 11B. Nucleophilic Aromatic Substitution through an Elimination Addition Mechanism: Benzyne Cl Na Na o C Phenol Br N 2 K :N 2 + KBr -33 o C Aniline Ch
41 The benzyne elimination addition mechanism Br Br (-N 3 ) (-Br ) N 2 Benzyne (or dehydrobenzene) N 2 N 2 + N 3 N 2 N 2 Ch
42 * N 2 * Cl K + * N 2 N 2 N 3 50% * elimination addition 50% N 2 Ch
43 CF 3 Cl NaN 2 N 3 (-NaCl) CF 3 N 2 m-(trifluoromethyl)aniline CF 3 Ch
44 X CF 3 > N 2 CF 3 N 2 less stable carbanion CF 3 CF 3 > N 3 more stable carbanion N 2 + N 2 N 2 Ch
45 Benzyne intermediates have been trapped through the use of Diels Alder reactions C C diazotization Anthranilic acid N 3 N N -C 2 -N 2 Benzyne (trapped in situ) Ch
46 11C. Phenylation Et + Br 2 NaN 2 liq. N 3 Et Ch
47 12. Spectroscopic Analysis of Phenols and Aryl alides Infrared spectra (IR) stretching: cm -1 R X R and R : characteristic absorptions of the benzene rings Ch
48 1 NMR spectra δ (ppm) of pure phenol: 2.55 in CCl 4 (1%) 5.63 δ ppm intramolecular hydrogen bonding Ch
49 Y (Y = or halides) δ 7 9 ppm Ch
50 13 C NMR spectra Y (Y = or halides) δ ppm Ch
51 Mass spectra Mass spectra of phenols often display a prominent molecular ion peak, M Phenols that have a benzylic hydrogen produce an M 1 peak that can be larger than the M peak Ch
52 END F CAPTER 21 Ch
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