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HOAÙ HOÏC HÖÕU CÔ Organic Chemistry CHÖÔNG 10 (t.t) ALCOHOLS & PHENOLS

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Presentation on theme: "HOAÙ HOÏC HÖÕU CÔ Organic Chemistry CHÖÔNG 10 (t.t) ALCOHOLS & PHENOLS"— Presentation transcript:

1 HOAÙ HOÏC HÖÕU CÔ Organic Chemistry CHÖÔNG 10 (t.t) ALCOHOLS & PHENOLS
Mendeleev Hamilton Hartree

2 GIÔÙI THIEÄU CHÖÔNG 10.1. RÖÔÏU 10.1.1.DANH PHAÙP & ÑOÀNG PHAÂN
CAÙC PHÖÔNG PHAÙP ÑIEÀU CHEÁ TÍNH CHAÁT ÖÙNG DUÏNG 10.2. PHENOL DANH PHAÙP & ÑOÀNG PHAÂN CAÙC PHÖÔNG PHAÙP ÑIEÀU CHEÁ TÍNH CHAÁT ÖÙNG DUÏNG

3 DANH PHAÙP

4 4-Bromo-3-methyl-phenol

5 2-(2-Hydroxyethyl)phenol
o-(2-Hydroxyethyl)phenol (o = ortho(1,2), m = meta(1,3), p = para(1,4))

6 C6-C1 : Alcohol, Aldehyde, Acid

7 C6

8 C6-C3 : Phenylpropanoid

9 C6-C3 : Coumarin, Chromone

10 C6-C4 :Napthoquinone

11 C6-C1-C6 : Xanthones Gentisin Guttiferae Gentian root

12 C6-C1-C6 : Xanthones Mangiferin Cratoxylem pruniflorum Swertia chirata
Hypericum Anti-inflammatory, antihepatotoxic, antiviral

13 C6-C2-C6 : Stilbenes Resveratrol Arachis,Cassia, Eucalyptus, Polygonum, Veratrum Antioxidant, anti-inflammatory, anticancer, coronary heart disease

14 C6-C2-C6 : Stilbenes Rhaponticin Rhapontic Rhubarb Blue in ultraviolet

15 C6-C2-C6 : Anthraquinone

16 C6-C3-C6 : Flavonoid

17 (C6-C3)2 : Lignans Magnolia officinalis M. obovata Magnoliaceae
CNS depressant, muscle relaxant, antiplatelet, antimicrobial, anticancer, insecticide

18 (C6-C3)2 : Lignans caffeic acid derivative
Echinacea angustifolia, E. purpurea (Coneflower) Compositae (Asteraceae) immunostimulant

19 (C6-C3-C6)2 : Biflavonoid Ginkgo spp Hypericum spp Rhus spp

20 (C6-C3-C6)2 : Biflavonoid Have activity against influenza A virus, HSV-1 and HSV-2 viruses

21 Capsicum Capsicum annuum (พริกหยวก), C. frutescens (พริกขี้หนู)
Solanaceae Counter irritant, relief of pain in osteoarthritis, post herpetic neuralgia and painful diabetic neuropathy

22 Uva Ursi / Bearberry leaves
Arctostaphylos uva-ursi Ericaceae diuretic, astringent, urinary antiseptic

23 Thyme Thymus vulgaris, T. zygis Labiatae
volatile oil 1.2% (thymol 36-55%, carvacrol 1-4%) antiseptic, antitussive, expectorant export : Spain

24 Clove (กานพลู) Syzygium aromaticum (Eugenia caryophyllus)
Myrtaceae volatile oil 14-21% (eugenol 84-95%) flavouring agent, stimulant, antiseptic Flower bud : Madagascar, Indonesia, Brazil Stem : Madagascar, Tanzania Leaves : Madagascar, Tanzania, Indonesia

25 Medicinol (clove) oil has a phenol content 85 - 90%
Deterioration Opt : phenol content low, use in pharmacy Strong : phenol content high, use in the manufacture of vanillin

26 Ginger Zingiber officinale Zingiberaceae
gingerol(an oily liquid consisting of homologous phenols) pungency of ginger inhibit prostaglandin synthetase (Anti-inflammatory) antiplatelet aggregation

27

28 CAÙC PHÖÔNG PHAÙP ÑIEÀU CHEÁ PHENOL

29 CAÙC PHÖÔNG PHAÙP ÑIEÀU CHEÁ PHENOL

30 ……. 1. Why does the reaction shift to the right?
2. Why is phenoxide ion stable? 3. Why is phenol acidic (compare to water)? …….

31 Resonance, Stability, Acid Strength
1. Resonance structures implies stability. 2. Stable anion implies the following reaction will proceed to the right, 3. Stable anion also implies that phenol is a stronger acid than water.

32 Substituted Phenol Which one is more acidic and why?

33 To examine the acid strength,

34 Resonance, Stability, Acid Strength
1. has more resonance structures than ,so it is more stable. 2. Fifth structure shows that nitro is an electron-withdrawing group. 3. Since 1 is true, that means is more reactive than . 4. Since 3 is true, is more acidic than . 5. See page 663 for para position effect.

35 Resonance, Stability, Acid Strength
pKa 9.95 10.17 1. Phenol is more acidic than p-methylphenol. 2. pKa indicates that CH3– is an electron-donating group.

36 Arrange the order of acidity (from highest to lowest) of the following compounds and explain why.

37 which enhances the aciditiy compare to phenol. The methoxy- of
Answer Key 4-nitrobenzylphenol (most acidic) phenol 4-methoxylphenol (least acidic) Reason: The nitro- on 4-nitrobenzylphenol is an electron-withdrawing group which enhances the aciditiy compare to phenol. The methoxy- of 4-methoxylphenol is an electron-donating group, thus it is less acidic than phenol.

38

39 PHAÛN ÖÙNG THEÁ AÙI ÑIEÄN TÖÛ CUÛA PHENOL

40 PHAÛN ÖÙNG THEÁ AÙI ÑIEÄN TÖÛ CUÛA PHENOL

41 PHAÛN ÖÙNG THEÁ AÙI ÑIEÄN TÖÛ CUÛA PHENOL

42 PHAÛN ÖÙNG THEÁ AÙI ÑIEÄN TÖÛ CUÛA PHENOL

43 ACYLATION OF PHENOL

44 ACYLATION OF PHENOL

45 ACYLATION OF PHENOL

46 ACYLATION OF PHENOL

47 ACYLATION OF PHENOL

48 PHAÛN ÖÙNG KOLBE-SCHMITT

49 PHAÛN ÖÙNG KOLBE-SCHMITT

50 PHAÛN ÖÙNG KOLBE-SCHMITT

51 PHAÛN ÖÙNG KOLBE-SCHMITT

52 PHAÛN ÖÙNG TAÏO ARYL ETHER

53 PHAÛN ÖÙNG OXI HOÙA PHENOL

54 PHAÛN ÖÙNG OXI HOÙA PHENOL

55 PHAÛN ÖÙNG OXI HOÙA PHENOL

56 CHAÁT ÑOÄC DA CAM VAØ DIOXIN

57 CHAÁT ÑOÄC DA CAM VAØ DIOXIN

58 CHAÁT ÑOÄC DA CAM VAØ DIOXIN

59 CAÛM ÔN SÖÏ THEO DOÕI CUÛA CAÙC BAÏN CHUÙC MOÏI ÑIEÀU TOÁT ÑEÏP


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