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

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

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

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

3 DANH PHAÙP

4 4-Bromo-3-methyl-phenol

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

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 Gentisin Guttiferae Gentian root Gentian root

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

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

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

15 C6-C2-C6 : Anthraquinone

16 C6-C3-C6 : Flavonoid

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

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

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

20 Have activity against influenza A virus, HSV-1 and HSV-2 viruses

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

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

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

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

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

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

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28 CAÙC PHÖÔNG PHAÙP ÑIEÀU CHEÁ PHENOL

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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 Which one is more acidic and why? Substituted Phenol

33 To examine the acid strength,

34 Resonance, Stability, Acid Strength 2. Fifth structure shows that nitro is an electron-withdrawing group. 1.has more resonance structures than,so it is more stable. 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 1. Phenol is more acidic than p-methylphenol. pK a pK a indicates that CH 3 – is an electron-donating group.

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

37 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.

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39 PHAÛN ÖÙNG THEÁ AÙI ÑIEÄN TÖÛ CUÛA PHENOL

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43 ACYLATION OF PHENOL

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48 PHAÛN ÖÙNG KOLBE-SCHMITT

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52 PHAÛN ÖÙNG TAÏO ARYL ETHER

53 PHAÛN ÖÙNG OXI HOÙA PHENOL

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56 CHAÁT ÑOÄC DA CAM VAØ DIOXIN

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


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