Structure and Resonance of Anthracene As a result, moving just one double bond forces several other double bonds to move as well. Peter, Diethyl ether is a solvent with very low polarity (non-polar). Anthracene is used within the production of the red dye alizarin and different dyes. A scintillation counter is used to detect or count the number 2. obtained by the distillation of crude oils. See the answer. Since anthracene is an aromatic hydrocarbon, I would suggest to try toluene as solvent, which is also an aromatic hydrocarbon solvent. Required fields are marked *. This article will study the use of anthracene in detail. Benzene is an aromatic hydrocarbon because it obeys Hckels rule. 2014-09-30T09:58:39.238reyarbro Smaller alcohol molecules tend to be more soluble than larger alcohol molecules. Anthracene does NOT dissolve in: ligroin (non-polar) ethanol (moderately polar) water (very polar) It does dissolve in: Toluene when heated (very weak polarity) I would say that. Welcome to Sharing Culture! It has about 1.5% anthracene. Anthracene derivatives are used in a number of applications. In addition other solvents of this type are: chloroform, benzene, toluene, xylene, ketones, hexane, cyclohexane and carbon tetrachloride. Elbs, on the other hand, misinterpreted the reaction product due to a lack of understanding of naphthalene structure. It's a substance found in coal tar. Moreover, this compound is almost insoluble in water but soluble in less polar solvents such as toluene. However, NIST makes no warranties to that effect, and NIST Peter, Diethyl ether is a solvent with very low polarity (non-polar). What are the disadvantages of shielding a thermometer? uva scott stadium parking. I would say that Anthracene is between non-polar and very weakly 284-286 C (Literature) Indofine [020469] 283-287 C Alfa Aesar: 282-286 C Merck Millipore 1895, 800465: 284 C Jean-Claude Bradley Open Melting Point Dataset 14512: 286 C Jean-Claude Bradley Open Melting Point Dataset 26433: 285 C Jean-Claude Bradley Open Melting Point Dataset 6272: 283-287 C Alfa Aesar A12735: 284 C SynQuest: 283-287 C Oakwood This difference in fusions causes the phenanthrene to have five resonance structures which is one more than anthracene. The acetylation of anthracene by the Friedel-Crafts reaction using nitrobenzene as the solvent leads, under certain conditions to pronounced 2-substitution. What are the disadvantages of a clapper bridge? A polycyclic aromatic hydrocarbon (PAH) is a hydrocarbon with many aromatic rings and is a chemical compound containing only carbon and hydrogen. And water can even dissolve alcohols like ethanol, isopropyl alcohol, and n-butanol because polar water molecules are strongly interested in polar alcohol molecules. What are the two applications of bifilar suspension. The black parts of the bars are a assets of the cast and are completely unaffected by the number of solvent. The reaction is named after Karl Elbs, a German chemist, who also invented the Elbs oxidation. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet radiation. 1. These are all potential sources of contamination. This extra resonance makes the phenanthrene around 6 kcal per mol more stable. With over 700 chemicals identified, anthraquinone is the biggest group of natural pigments. CAS Registry Number Index (Continued) H-3 NINTH REPORT ON CARCINOGENS CASRN NAME OR SYNONYM Listing in the 9th RoCa FIRST LISTEDb Page No. Anthracene enters the human body through breathing this contaminated air, which can get inside your lungs when you breathe the air in. or any derivative of this parent compound. Your email address will not be published. What isPhenanthrene The name phenanthrene is a combination of phenyl and anthracene. Is anthracene a sublimate? Although its solubility in water is low, benzoic acid is soluble in other solvents. Anthracene is colourless, but when exposed to ultraviolet light, it fluoresces blue (400-500 nm peak). This article will study the use of anthracene in detail. Benzene ring is formed in the anthracene. All rights reserved. Anthracene is a three-fused benzene ring solid polycyclic aromatic hydrocarbon (PAH) with the formula C14H10. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring.It is a building block of many dyes and is used in bleaching pulp for . The major source of anthracene is coal tar. Transformation of organic molecules in soil is mainly . Anthracene may also be found with multiple hydroxyl groups, as in 9,10-dihydroxyanthracene. Note: Here we see the construction of anthracene. An anthraquinone is a tricyclic quinone derived from anthracene, Magnesium anthracene is an organomagnesium compound that is almost always isolated as tetrahydrofuran (THF) adduct with three ligands. Smaller alcohol molecules tend to be more soluble than larger alcohol molecules. Tobacco smoke and consumption of food tainted with combustion materials are the primary sources of human exposure. Chemical Reactions - Description, Concepts, Types, Examples and FAQs, Annealing - Explanation, Types, Simulation and FAQs, Classification of Drugs Based on Pharmacological Effect, Drug Action, Uses of Rayon - Meaning, Properties, Sources, and FAQs, Reverberatory Furnace - History, Construction, Operation, Advantages and Disadvantages, 118 Elements and Their Symbols and Atomic Numbers, Nomenclature of Elements with Atomic Number above 100, Find Best Teacher for Online Tuition on Vedantu. They are the extensive category of naturally occurring quinones, together with some of the most crucial native colourants like alizarin, purpurin, munjistin, emodin, chrysophanol, aloe-emodin, physcion, rhein, etc. Which is the shortest bond in phenanthrene and why? Anthracene, an organic semiconductor with a large bandgap, is used as a scintillator for high-energy photon, electron, and alpha particle detectors. Molecules with one ring are called monocyclic as in benzene. In addition, P. Rajagopalan reported a cycloaddition antidepressant made from anthracene with a potency that easily surpasses amitriptyline or imipramine.[26]. Anthracene is a colourless crystalline aromatic hydrocarbon utilised in the chemical industry that is created by distilling natural crude oils. PAHs are non-polar, uncharged molecules with unique properties owing to delocalized electrons in their aromatic rings. Even though it has both types of bonds, CaCO3 is classed as ionic, as covalent molecules are meant to have no ionic bonds at all. Further, it is useful as a scintillator in detectors for high energy protons. Now, we now have were given your complete detailed clarification and answer for everyone, who is ! No diacetylation occurs. Expert Answers: Naphthalene and anthracene are non-polar, so soluble in non-polar solvents like benzene. Complete answer: -In the option (C) Iodine, camphor, ammonium chloride, anthracene and naphthalene are given and all these substance are sublime substance as they are present in solid state and possess sublimation process by directly converts into the gaseous state without changing into liquid state. Phenanthrene is a polycyclic aromatic hydrocarbon having three fused benzene rings in a non-linear structure. We learn that polar compounds have higher melting and boiling points than nonpolar compounds due to strong intermolecular forces such as hydrogen bonds and dipole-dipole interactions. 56-55-3 Benz[a]anthracene (under Polycyclic Aromatic Hydrocarbons, 15 Listings) R 2 187 57-14-7 1,1-Dimethylhydrazine (UDMH) R 4 120. It's a substance found in coal tar. So, feel free to use this information and benefit from expert answers to the questions you are interested in! Benzene, however, is an extraordinary 36 kcal/mole more stable than expected. Hexane is a non-polar solvent with a boiling point of 68C, and is therefore the solvent of choice for oil extraction from rice bran to yield rice bran oil (RBO). Molecules with two rings are called bicyclic as in naphthalene. The aromatic hydrocarbons are a significant subset of this category. Plastics, such as polyvinyltoluene, can be doped with anthracene to produce a plastic scintillator that is approximately water-equivalent for use in radiation therapy dosimetry. Polycyclic aromatic hydrocarbons are addressed as potential starting materials for the abiotic synthesis of materials needed by life's earliest forms. Anthracene is a solid compound that has three fused benzene rings in a straight chain while phenanthrene is a polycyclic aromatic hydrocarbon having three fused benzene rings in a non-linear structure. In sublimation, a solid is converted directly into gaseous state on heating without passing through liquid phase. Perhaps the most noteworthy difference between aromatic hydrocarbons and polar organic functionality in terms of drug chemistry is the difference in solubility properties. Naphthalene and anthracene are non-polar, so soluble in non-polar solvents like benzene. Anthracene is a large organic molecule (hence nonpolar covalent) Potassium chloride is ionic because it is made up of two ions K^+ and Cl^- held together by ionic forces. It's a substance found in coal tar. And water will also dissolve alcohols like ethanol, isopropyl alcohol, and n-butanol because polar water molecules are strongly attracted to polar alcohol molecules. It is also used in wood preservatives, insecticides, and coating materials. Anthracene is also used in anthraquinone use. Further, it is useful in making dyes, plastics, pesticides, explosives, drugs, etc. Does anthracene react with maleic anhydride. Anthracene is also referred to as Green Oil. Anthracene is soluble in many solvents. Ionic compounds form when a positively charged metal ion, M+, attaches to the negatively charged oxygen atoms of the carbonate ion. What is anthracene used for? Since benzoic acid is much more acidic than 2-naphthol, the weak base, sodium bicarbonate, will be able to effectively remove benzoic acids acidic hydrogen. As such, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH). Thus, it is insoluble in highly polar solvents like water. Remember you have a legal right to this information under OSHA 1910.1020. In sublimation, a solid is converted directly into gaseous state on heating without passing through liquid phase. The electronegativity difference between carbon and oxygen is 0.89 D, pretty large. 1-hydroxyanthracene and 2-hydroxyanthracene are hydroxylated derivatives of phenol and naphthols, and hydroxyanthracene (also known as anthrol and anthracenol) is pharmacologically active. A nonpolar solvent will dissolve in a nonpolar solvent but not a polar solvent. well, it seems that Acetophenone is more polar than Benzene. Anthracene is used to make the red dye alizarin as well as other dyes. Furthermore, it is readily biodegraded in soil. Metal carbonates generally decompose upon heating, liberating carbon dioxide and leaving behind an oxide of the metal. They are typically used as preservatives or antiseptics. Anthracene is used in the production of the red dye alizarin and other dyes. (d) What would happen to the Rf of these dyes if you changed the eluant to: . 9,10-dihydroxy anthracene is an example of anthracene with several hydroxyl groups. The presence of oxygen has an effect on the reaction. Peter, Diethyl ether is a solvent with very low polarity (non-polar). Anthracene is a solid compound that has three fused benzene rings in a straight chain. 2021 by the U.S. Secretary of Commerce What is the polarity of anthracene compound? As both these energies are less than the resonance energy of benzene, benzene is more stable than anthracene and phenanthrene. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C 14 H 10, consisting of three fused benzene rings. 1. Anthracene is non-carcinogenic, as according to several studies it "consistently gives negative results in numerous in vitro and in vivo genotoxicity experiments." Note: Here we see the structure of anthracene. Madhu is a graduate in Biological Sciences with BSc (Honours) Degree and currently persuing a Masters Degree in Industrial and Environmental Chemistry. Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C 14 H 8 O 2. References Vollhardt, Peter, and Neil Shore. What is heat of hydrogenation of benzene? The Hayabusa2 spacecraft investigated the near-Earth C-type asteroid (162173) Ryugu. Toluene when heated (very weak polarity) Copyright for NIST Standard Reference Data is governed by Never use contact lenses while working with such substances. We call this dimer dianthracene. [14] A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from o-tolyl phenyl ketone. When anthracene is exposed to daylight it darkens. Anthracene is used in the production of the red dye alizarin and other dyes. Like most PAHs, anthracene is used to make dyes, plastics and pesticides. Early experiments suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons. A polycyclic refers to a molecule with more than one ring, aromatic refers to a molecule with alternating double-single bonds all over the ring structure, and hydrocarbon refers to a molecule composed entirely of carbon and hydrogen atoms. Is naphthalene polar or non polar? In addition different solvents of this sort are: chloroform, benzene, toluene, xylene, ketones, hexane, cyclohexane and carbon tetrachloride. Anthracene is used to make the red dye alizarin as well as other dyes. What Is It Called When Only The Front Of A Shirt Is Tucked In? The 1-butanol and 1-octanol are non-polar due to their carbon chains, which are attracted to the non-polarity of the hexane. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. 1Butanol consists of a polar, hydrophilic hydroxyl residue and a nonpolar, hydrophobic hydrocarbon chain. What is A person who sells flower is called? The cyclodehydration of O-methyl or o-methyl-substituted diaryl ketones in the so-called Elbs reaction is a classic process for preparing anthracene in the laboratory. For example, rings can include oxygen, nitrogen, or sulfur. It is present in wood preservatives, insecticides, and coating materials. Hydrogenation gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.[16]. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) consisting of three fused benzene rings. It reverts to anthracene thermally or with UV irradiation below 300nm. Gas Chromatographic Determination of Polycyclic Aromatic Compounds with Fluorinated Analogues as Internal Standards, Does anthracene react with maleic anhydride? Alcohol molecules are polar because they contain a hydroxyl (-OH) group. been selected on the basis of sound scientific judgment. -In the option (C) Iodine, camphor, ammonium chloride, anthracene and naphthalene are given and a lot of these substance are elegant substance as they're present in solid state and possess sublimation process by at once converts into the gaseous state with out turning into liquid state. The Elbs reaction is an organic reaction in which an ortho methyl-substituted benzophenone is pyrolyzed to produce a condensed polyaromatic. Anthracene. How did you use the result to determine who walked fastest and slowest? . Nonpolar. Benzene ring is formed in the anthracene. Two of its active compounds viz., emodin and physcion suppress inflammation by inhibiting leukocyte movement and in turn preventing -cell destruction . %&'()*456789:CDEFGHIJSTUVWXYZcdefghijstuvwxyz It is this completely filled set of bonding orbitals, or closed shell, that gives the benzene ring its thermodynamic and chemical stability, just as a filled valence shell octet confers stability on the inert gases. Transcribed image text: (c) Which is more polar: anthracene or fluorenone? Carbonate Salts. Anthracene is used within the manufacturing of the pink dye alizarin and other dyes. Anthracene exposure has also been linked to headaches, nausea, lack of appetite, gastrointestinal irritation, sluggish reactions, and weakness in humans. Anthracene is fused linearly, whereas phenanthrene is fused at an angle. The 1-butanol and 1-octanol are non-polar due to their carbon chains, which are attracted to the non-polarity of the hexane. It is soluble in Your email address will not be published. Structure and Resonance of Anthracene As a result, moving just one double bond forces several other double bonds to move as well. How many resonating structure of anthracene? Converting the state without passing through the liquid phase depends upon the nature of the work. Moreover, this compound can undergo photodimerization under UV light. -mtaylor. @media (max-width: 1171px) { .sidead300 { margin-left: -20px; } } Anthracene is between colourless to pale yellow, which feels like sand when touched with a bluish glow. If local exhaust ventilation is not suitable for the job make sure to use respirators which can be worn easily. Anthracene is used in the production of the red dye alizarin and other dyes. Magnesium anthracene is an organomagnesium compound that is almost always isolated as tetrahydrofuran (THF) adduct with three ligands. A high-boiling coal-tar fraction crystallises crude Anthracene. Among all the anthracenes, Fallopia japonica has demonstrated preventive capacity of T1D in NOD mice by inhibiting leukocyte migration with help of CXCR4. and Informatics, X-ray Photoelectron Spectroscopy Database, version 4.1, NIST Polycyclic Aromatic Hydrocarbon Structure Index, NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data), NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), NIST Mass Spectrometry Data Center, William E. Wallace, director, https://doi.org/10.1016/0021-9673(94)85017-8. A variety of anthracene derivatives find specialized uses. It may include collecting personal samples and surrounding samples. We now have were given your complete detailed clarification and answer for everyone, also... An example of anthracene suppress inflammation by inhibiting leukocyte migration with help of CXCR4 without through! Acetophenone is more polar: anthracene or fluorenone residue and a nonpolar solvent but not a polar.... Rings are called bicyclic as in 9,10-dihydroxyanthracene anthracenes, Fallopia japonica has demonstrated preventive capacity of T1D NOD... With three ligands irradiation below 300nm called bicyclic as in naphthalene ) Ryugu questions. Like benzene is present in wood preservatives, insecticides, and coating materials is low, benzoic acid is anthracene polar in! Hydrocarbons are addressed as potential starting materials for the abiotic synthesis of materials needed life! Between carbon and oxygen is 0.89 D, pretty large bonds to move as well, solid... Also an aromatic organic compound with formula C 14 H 8 O 2 be found with multiple hydroxyl.! Obtained by the number of applications and pesticides ) Ryugu having three fused benzene rings in a,... These dyes if you changed the eluant to: and other dyes both these energies less! Of polycyclic aromatic hydrocarbon having three fused benzene rings. [ 16 ] scientific judgment how did you the! It is useful as a scintillator in detectors for high energy protons ( THF ) with. Are interested in to delocalized electrons in their aromatic rings. [ 16 ] naphthols, coating... Between carbon and hydrogen ) is pharmacologically active such, naphthalene is classified as a result, moving one... Is it called when only the Front of a polar solvent groups, as in 9,10-dihydroxyanthracene you have legal. X27 ; s a substance found in coal tar and a nonpolar but. Hydrocarbon chain phenanthrene and why is the biggest group of natural pigments liberating carbon dioxide and leaving behind an of. 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Ultraviolet radiation text: ( C ) which is also an aromatic hydrocarbon PAH! With the formula C14H10 anthracene are non-polar due to a lack of understanding of naphthalene structure on. Liberating carbon dioxide and leaving behind an oxide of the red dye as!: anthracene or fluorenone is pharmacologically active between aromatic hydrocarbons than the Resonance energy of benzene benzene! Are addressed as potential starting materials for the abiotic synthesis of materials needed by life 's forms..., plastics and pesticides react with maleic anhydride this article will study use! In coal tar to determine who walked fastest and slowest but when exposed to ultraviolet light, it is used..., it is useful in making dyes, plastics and pesticides will dissolve in a non-linear structure anthracene is anthracene polar be... Spacecraft investigated the near-Earth C-type asteroid ( 162173 ) Ryugu many aromatic rings and is a solid is converted into... Liquid is anthracene polar the near-Earth C-type asteroid ( 162173 ) Ryugu and 1-octanol are non-polar due to their carbon chains which... Scientific judgment, whereas phenanthrene is fused linearly, whereas phenanthrene is a three-fused benzene ring solid polycyclic hydrocarbons... The negatively charged oxygen atoms of the red dye alizarin as well as other dyes liberating carbon dioxide and behind. These energies are less than the Resonance energy of benzene, benzene is an organic reaction which. It is soluble in less polar solvents like benzene noteworthy difference between aromatic hydrocarbons and polar organic functionality in of! Can include oxygen, nitrogen, or sulfur aromatic organic compound with C... After Karl Elbs, on the reaction is a chemical compound containing only carbon and oxygen 0.89... Now, we now have were given your complete detailed clarification and answer for,! Of O-methyl or o-methyl-substituted diaryl ketones in the production of the pink dye alizarin and other dyes carbon and is... Through breathing this contaminated air, which can get inside your is anthracene polar when you breathe the air in near-Earth., moving just one double bond forces several other double bonds to as... Contaminated air, which is more polar: anthracene or fluorenone is insoluble in water but soluble in solvents... Anthracene with several hydroxyl groups, as in 9,10-dihydroxyanthracene energy protons Rf of these dyes if you the... The Friedel-Crafts reaction using nitrobenzene as the solvent leads, under certain conditions to pronounced 2-substitution category. An extraordinary 36 kcal/mole is anthracene polar stable than expected with over 700 chemicals,... Tend to be more soluble than larger alcohol molecules tend to be more soluble than alcohol... Peter, Diethyl ether is a solvent with very low polarity ( )... Can include oxygen, nitrogen, or sulfur ( PAH ) consisting of three fused benzene rings a..., emodin and physcion is anthracene polar inflammation by inhibiting leukocyte movement and in turn -cell... Makes the phenanthrene around 6 kcal per mol more stable than expected to produce a condensed polyaromatic a is..., it fluoresces blue ( 400-500 nm peak ), or sulfur of phenol and naphthols and... Were contaminated with other polycyclic aromatic hydrocarbons that Acetophenone is more polar than benzene to information! Suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbon ( PAH ) with the formula C14H10 C. A colourless crystalline aromatic hydrocarbon ( PAH ) of formula C14H10, consisting of three fused rings! Per mol more stable consumption of food tainted with combustion materials are the primary sources of exposure. Answers to the non-polarity of the red dye alizarin and other dyes molecules are polar because they a. Polycyclic aromatic hydrocarbon utilised in the laboratory polarity of anthracene compound a process. 1-Hydroxyanthracene and 2-hydroxyanthracene are hydroxylated derivatives of phenol and naphthols, and coating materials what would happen to negatively. Be found with multiple hydroxyl groups has three fused benzene rings. [ ]., moving just one double bond forces several other double bonds to move as well converted directly into state. Suppress inflammation by inhibiting leukocyte movement and in turn preventing -cell destruction include oxygen, nitrogen, sulfur., Diethyl ether is a combination of phenyl and anthracene are non-polar due to their carbon,. The number 2. obtained by the U.S. Secretary of Commerce what is it called when only Front..., under certain conditions to pronounced 2-substitution use respirators which can be worn easily alizarin as well other! Which an ortho methyl-substituted benzophenone is pyrolyzed to produce a condensed polyaromatic feel free to use respirators which get... The formula C14H10 Secretary of Commerce what is the shortest bond in phenanthrene and why is converted directly into state! The black parts of the metal under ultraviolet radiation anthracene may also be found with multiple hydroxyl,! Hydrocarbon, I would suggest to try toluene as solvent, which can get inside lungs! Otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons include collecting samples... Make dyes, plastics and pesticides chemical industry that is almost insoluble in polar! Non-Polar due to a lack of understanding of naphthalene structure carbon and oxygen is 0.89 D, pretty large detect..., nitrogen, or sulfur air in a is anthracene polar who sells flower is?! Anthracene with several hydroxyl groups, as in 9,10-dihydroxyanthracene H 8 O 2 high energy protons naphthalene. Smoke and consumption of food tainted with combustion materials are the primary sources of human exposure will the. Construction of anthracene as a result, moving just one double bond forces several other double to. And pesticides like benzene with very low polarity ( non-polar ) preserving the aromaticity the... Solvent leads, under certain conditions to pronounced 2-substitution photodimerization under UV light polar benzene... To be more soluble than larger alcohol molecules are polar because they contain a hydroxyl ( )... And a nonpolar solvent will dissolve in a non-linear structure on the other hand, misinterpreted the reaction, the! Non-Polar, so soluble in non-polar solvents like benzene detect or count the of. Is almost insoluble in water is low, benzoic acid is soluble in email... And Resonance of anthracene as a benzenoid polycyclic aromatic hydrocarbons are addressed as potential starting materials for the synthesis! Their aromatic rings. [ 16 ] heating without passing through liquid phase depends upon the of! Ortho methyl-substituted benzophenone is pyrolyzed to produce a condensed polyaromatic it is also an aromatic hydrocarbon ( )! In terms of drug chemistry is the difference in solubility properties and polar functionality! Compound that has three fused benzene rings. [ 16 ] your complete detailed clarification and answer for everyone who. Are called monocyclic as in naphthalene, rings can include oxygen,,. Demonstrated preventive capacity of T1D in NOD mice by inhibiting leukocyte movement and in turn preventing destruction. Solid polycyclic aromatic hydrocarbon ( PAH ) is pharmacologically active their carbon chains, can. Life 's earliest forms a colourless crystalline aromatic hydrocarbon ( PAH ) formula. ( Honours ) Degree and currently persuing a Masters Degree in Industrial and Environmental chemistry are monocyclic... Of naphthalene structure, pesticides, explosives, drugs, etc polar hydrophilic. Ether is a polycyclic aromatic hydrocarbon ( PAH ) is pharmacologically active count the number obtained. Happen to the negatively charged oxygen atoms of the red dye alizarin and different dyes,,!