Hoa huu co _phenol

HOÁ HỌC HỮU CƠ
Organic Chemistry
CHƯƠNG 10 (t.t)
ALCOHOLS & PHENOLS
Mendeleev
Hamilton
Hartree
GIỚI THIỆU CHƯƠNG
10.1. RƯỢU
10.1.1.DANH PHÁP & ĐỒNG PHÂN
10.1.2.CÁC PHƯƠNG PHÁP ĐIỀU CHẾ
10.1.3. TÍNH CHẤT
10.1.4.ỨNG DỤNG

10.2. PHENOL
10.2.1. DANH PHÁP & ĐỒNG PHÂN
10.2.2. CÁC PHƯƠNG PHÁP ĐIỀU CHẾ
10.2.3. TÍNH CHẤT
10.2.4. ỨNG DỤNG


DANH PHÁP
4-Bromo-3-methyl-phenol
o-(2-Hydroxyethyl)phenol
2-(2-Hydroxyethyl)phenol
C6-C1 : Alcohol, Aldehyde, Acid
C6
C6-C3 : Phenylpropanoid
C6-C3 : Coumarin, Chromone

C6-C4 :Napthoquinone
C6-C1-C6 : Xanthones
Gentisin Guttiferae
Gentian root
C6-C1-C6 : Xanthones
Mangiferin Cratoxylem pruniflorum
Swertia chirata
Hypericum
Anti-inflammatory, antihepatotoxic, antiviral
C6-C2-C6 : Stilbenes
Resveratrol Arachis,Cassia, Eucalyptus, Polygonum, Veratrum
Antioxidant, anti-inflammatory, anticancer, coronary heart disease
C6-C2-C6 : Stilbenes
Rhaponticin Rhapontic Rhubarb
Blue in ultraviolet
C6-C2-C6 : Anthraquinone
C6-C3-C6 : Flavonoid
(C6-C3)2 : Lignans
Magnolia officinalis
M. obovata
Magnoliaceae
CNS depressant, muscle relaxant, antiplatelet, antimicrobial, anticancer, insecticide
(C6-C3)2 : Lignans
caffeic acid derivative
Echinacea angustifolia, E. purpurea (Coneflower)
Compositae (Asteraceae)
immunostimulant
Ginkgo spp
Hypericum spp
Rhus spp
(C6-C3-C6)2 : Biflavonoid
(C6-C3-C6)2 : Biflavonoid
Have activity against influenza A virus, HSV-1 and HSV-2 viruses
Capsicum
Capsicum annuum (พริกหยวก), C. frutescens (พริกขี้หนู)
Solanaceae
Counter irritant, relief of pain in osteoarthritis, post herpetic neuralgia and painful diabetic neuropathy
Uva Ursi / Bearberry leaves
Arctostaphylos uva-ursi
Ericaceae
diuretic, astringent, urinary antiseptic
Thyme
Thymus vulgaris, T. zygis
Labiatae
volatile oil 1.2% (thymol 36-55%, carvacrol 1-4%)
antiseptic, antitussive, expectorant
export : Spain
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
Opt : phenol content low, use in pharmacy
Strong : phenol content high, use in the manufacture
of vanillin
Medicinol (clove) oil has a phenol content 85 - 90%
Deterioration
Ginger
Zingiber officinale
Zingiberaceae
gingerol(an oily liquid consisting of homologous phenols)
pungency of ginger
inhibit prostaglandin synthetase (Anti-inflammatory)
antiplatelet aggregation
CÁC PHƯƠNG PHÁP ĐIỀU CHẾ PHENOL
CÁC PHƯƠNG PHÁP ĐIỀU CHẾ PHENOL
1. Why does the reaction shift to the right?
2. Why is phenoxide ion stable?
3. Why is phenol acidic (compare to water)?
…….
Resonance, Stability, Acid Strength
1. Resonance structures implies stability.
3. Stable anion also implies that phenol is a stronger acid than water.
Which one is more acidic and why?
Substituted Phenol
To examine the acid strength,
Resonance, Stability, Acid Strength
2. Fifth structure shows that nitro is an electron-withdrawing group.
5. See page 663 for para position effect.
Resonance, Stability, Acid Strength
1. Phenol is more acidic than p-methylphenol.
2. pKa indicates that CH3– is an electron-donating group.
Arrange the order of acidity (from highest to lowest) of the following compounds and explain why.
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.
PHẢN ỨNG THẾ ÁI ĐIỆN TỬ CỦA PHENOL
PHẢN ỨNG THẾ ÁI ĐIỆN TỬ CỦA PHENOL
PHẢN ỨNG THẾ ÁI ĐIỆN TỬ CỦA PHENOL
PHẢN ỨNG THẾ ÁI ĐIỆN TỬ CỦA PHENOL
ACYLATION OF PHENOL
ACYLATION OF PHENOL
ACYLATION OF PHENOL
ACYLATION OF PHENOL
ACYLATION OF PHENOL
PHẢN ỨNG KOLBE-SCHMITT
PHẢN ỨNG KOLBE-SCHMITT
PHẢN ỨNG KOLBE-SCHMITT
PHẢN ỨNG KOLBE-SCHMITT
PHẢN ỨNG TẠO ARYL ETHER
PHẢN ỨNG OXI HÓA PHENOL
PHẢN ỨNG OXI HÓA PHENOL
PHẢN ỨNG OXI HÓA PHENOL
CHẤT ĐỘC DA CAM VÀ DIOXIN
CHẤT ĐỘC DA CAM VÀ DIOXIN
CHẤT ĐỘC DA CAM VÀ DIOXIN
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