Oxidation of alcohols. This experiment will mostly consist of the oxidation of 9-fluorenol, which is a secondary alcohol. Tertiary alcohols do not undergo oxidation. Oxidising Alcohols to Aldehydes and Ketones is important in modern-day synthetic chemistry. It is an oxidation reaction from an -OH to an -OOH. Hydroboration-Oxidation is a two step pathway used to produce alcohols. Oxidation of Alcohol => When we produce ketones, aldehydes and carboxylic acids, we oxidize alcohols. You need to be able to remove those two particular hydrogen atoms in order to set up the carbon-oxygen double bond. Compounds containing the ketone or aldehyde functional group are important in organic chemistry. Depending on the reaction and structure of the (1 . Experiment 6 - Alcohols and Phenols. FIGURE 3. The reactant (1S)-borneol also emerged as an impurity based on the literature spectrums of Oxidation of Alcohols: Solid-Supported Oxidation and Qualitative Tests Relevant sections in the text: Fox & Whitesell, 3 rd Ed. ingested; PCC oxidizes 1o alcohols one rung up the oxidation ladder, turning primary alcohols into aldehydes and secondary alcohols into ketones. A water-soluble Cp*Ir complex bearing a bipyridine-based functional ligand can be used as catalyst for a dehydrogenative oxidation of various primary and secondary alcohols to aldehydes and ketones, respectively without any oxidant. The reaction involves the orange solution of dichromate ions turning green as chromium (III) ions are formed. Chromic Acid is commonly represented by any of these three in an undergraduate organic . bit of a problem during the experiment when our product wouldnt dry out after we added the The experiment has three parts, all of which can be done in one laboratory session. The full equation for the oxidation of ethanol to ethanoic acid is as follows: (3) 3 C H 3 C H 2 O H + 2 C r 2 O 7 2 + 16 H + 3 C H 3 C O O H + 4 C r 3 + + 11 H 2 O. For test tube 2, the methanol was mixed with sulfuric acid. Let This catalytic dehydrogenation reaction produces aldehydes (as shown below) and ketones, and since the carbon atom bonded to the oxygen is oxidized, such alcohol to carbonyl conversions are generally referred to as oxidation reactions. B. Oxidation of Alcohols. Millions of scientists, educators and students at thousands of . There are many biological oxidations that convert a primary or secondary alcohol to a carbonyl compound. Furthermore, the borane acts as a lewis acid by accepting two electrons in its empty p orbital from an alkene . The information I gathered from the H NMR spectrum is to help identify and to also confirm the to produce carboxylic acids. Identifying Alcohols. Oxidation of Benzyl Alcohol to Benzaldehyde. Conversions of alcohols to aldehydes and ketones are among the most important and widely used oxidation reactions in organic chemistry. To calculate the oxidation state of a carbon atom the following rules are used: When looking at the oxidation states of carbon in the common functional groups shown below it can be said that carbon loses electron density as it becomes more oxidized. An excess of the oxidizing agent must be used, and the aldehyde formed as the half-way product should remain in the mixture. In this experiment the process will be simulated by using a mild oxidizing agent Pre-lab 3 - Williamson Ether Synthesis of 4-Bromophenol Pre-Lab, Pre-lab 7 ochem 2 - Microwave- Assisted Reduction of Aldehydes and Ketones by Sodium Borohydride, 2212 Lab 7 - Reduction of Ketones and Aldehydes, O Chem2 #1-2 - Full pre and post lab of oxidation of an unknown alcohol at the university go, Introduction to Structured Query Language (DAD220), 21st Century Skills: Critical Thinking and Problem Solving (PHI-105), Introduction to Human Psychology (PSYC 1111), American Politics and US Constitution (C963), Communication As Critical Inquiry (COM 110), Introduction to Anatomy and Physiology (BIO210), Differential Diagnosis & Primary Care Practicum (NR-511), Professional Application in Service Learning I (LDR-461), Advanced Anatomy & Physiology for Health Professions (NUR 4904), Principles Of Environmental Science (ENV 100), Operating Systems 2 (proctored course) (CS 3307), Comparative Programming Languages (CS 4402), Business Core Capstone: An Integrated Application (D083), EES 150 Lesson 2 Our Restless Planet Structure, Energy, & Change, Database Systems Design Implementation and Management 9th Edition Coronel Solution Manual, Lesson 6 Plate Tectonics Geology's Unifying Theory Part 2, Lesson 10 Earthquake Hazards, Magnitude, and Intensity, Death Penalty Research Paper - Can Capital Punishment Ever Be Justified, Skomer Casey, BIO 115 Final Review - Organizers for Bio 115, everything you need to know, MMC2604 Chapter 1 Notesm - Media and Culture: Mass Communication in a Digital Age, Mark Klimek Nclexgold - Lecture notes 1-12, NHA CCMA Practice Test Questions and Answers, Essentials of Psychiatric Mental Health Nursing 8e Morgan, Townsend, Module One Short Answer - Information Literacy, The cell Anatomy and division. It is important to note that the hydride adds exclusively to the Re face of the pyridine ring giving NADH a pro-R stereochemistry. Chromic acid, also known as Jones reagent, is prepared by adding chromium trioxide (CrO3) to aqueous sulfuric acid. PCC is being replaced in laboratories by DessMartin periodinane (DMP) in dichloromethane solvent, which has several practical advantages over PCC, such as producing higher yields and requiring less rigorous conditions (lower reaction temperature and a nonacidic medium). suggesting ethyl acetate or brine was left over. Many alcohols react with oxidizing agents to produce new chemical compounds. Primary alcohols can be oxidised to form aldehydes which can undergo further oxidation to form carboxylic acids. contact with eyes You will do four chemical tests: (1) Chromic Acid Test (or Jones Oxidation), (2) Ritter Test using potassium permanganate (3) the Lucas Test using ZnCl 2 and HCl, and (4) the Iodoform Test. Investigate the oxidation of ethanol Core practical 5: Investigate the oxidation of ethanol Objective To oxidise ethanol and use heating under reflux and distillation as practical technique s Safety r goggles Wea. (C) The enzyme lactic acid dehydrogenase catalyses this reaction, and it functions only with the L-enantiomer of lactic acid. The melting point range for this product is -75 C, and the point range is between 114-116 C. The FIGURE 1. The techniques that will be used in this experiment will include, quenching, and also liquid/liquid extraction, the reaction mixture will first be te, starch for excess oxidant, quenched with sa, and once the oxidized product has been isolated its FTIR and H NMR spectra will be use, Psychology (David G. Myers; C. Nathan DeWall), Civilization and its Discontents (Sigmund Freud), The Methodology of the Social Sciences (Max Weber), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Give Me Liberty! In this experiment using a microscale well-plate, students add acidified dichromate (VI) to primary, secondary and tertiary alcohols to observe the difference in their oxidation reactions. Oxidation Reactions of Alcohols. (EPR) experiments were performed by adding the radical spin trapping agent DMPO . Abstract. (ii) Give a suitable reagent and reaction conditions for the oxidation of Ethanol to form the Carboxylic acid as the major product. to this unusual yield. The sublimation process should have efficiently The potassium permanganate solution will become yellowish. Add 5 more mL of dichloromethane to the aqueous layer and extract the organic layer Objective The purpose of this experiment is to oxidize cyclohexanone with concentrated nitric acid in a highly exothermic reaction. hypochlorous acid. The general idea of oxidation and reduction reactions learned in general chemistry is that when a compound or atom is oxidized it loses electrons, and when it is reduced it gains electrons. The oxidation of a diol with active MnO2 produces the selective oxidation of an allylic alcohol as the major reaction pathway, with a 10-20% of product arising from oxidation of both alcohols and 5% of a product resulting from an intramolecular attack of an alcohol on the enone being the primary oxidation product. Secondary alcohols are cleanly oxidized to ketones. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. 1 Introduction and Scope. The Oxidation of Alcohols. Schiff's reagent is a fuchsin dye decolorized by passing sulfur dioxide through it. hazardous if in These reactions are mild, efficient, and safe. This peak best represented the, contamination because the other peaks lied in the same region as the peaks of camphor and therefore Secondary alcohols can be oxidised to form ketones only. Modern undergraduate organic chemistry textbooks typically present a number of methods to effect these reactions, and among the most commonly featured ox The latter considerations explain why such oxidants are rarely used in large-scale industrial synthesis of . In this experiment you will learn how to dehydrate an alcohol to form an alkene using a strong acid catalyst. This reaction is used to make aldehydes, ketones and carboxylic acids, and as a way of distinguishing between primary, secondary and tertiary alcohols. This very complex molecule functions to accept hydride (H:-) or the equivalent (H++ 2e) from the carbon of an alcohol. In this demonstration, various alcohols are heated with acidified potassium dichromate solution.During this test, primary and secondary alcohols are oxidised. bz; mcs EtOH, That beaker was then placed on a hot plate at medium heat, and covered with a glass and container of ice water. Use this practical to investigate the oxidation reactions of various alcohols with acidified potassium dichromate. INTRODUCTION The objective of this experiment is to produce camphor through the oxidation of (1S)-borneol at. The higher the number of the alkyl connected to the alpha carbon atom the harder the oxidation of the alcohol. Therefore, it can be suggested that the increase in melting point was due to the (1S)-borneol impurity. In this experiment you will oxidize the alcohol group in isoborneol to the ketone group in camphor using sodium hypochlorite: H3C H3C CH3 OH H3C H3C CH3 NaOCl O and skin; irritation This enzyme functions only with L-malic acid: Draw the alcohol that the following ketones/aldehydes would have resulted from if oxidized. Add 5 mL of dichloromethane to the solution. glacial acetic acid: clear in color, strong odor. This reduced compound is also called the oxidizing agent. The alcohol is heated under reflux with an excess of the oxidizing agent. False. After shaking vigorously and allowing the funnel to sit for a minute, two distinct layers were observed. The experimental IR spectra further supports the presence of (1S)-borneol in the camphor sample, (fig. To In addition to CrO3, other commonly used oxidizing agents include potassium permanganate (KMnO4) and sodium dichromate (Na2Cr2O7). DMP is named after Daniel Dess and James Martin, who developed it in 1983. eyes and skin; Because of the color change to the acidified potassium dichromate(VI) solution, you must, therefore, have a secondary alcohol. Unlike chromic acid, PCC will not oxidize aldehydes to carboxylic acids. 66 g- 100 mL round bottom flask- starting, Volume of saturated sodium bisulfite: 10 mL. The next step is a concerted E2-like reaction where a hydrogen is removed from the alcohol, the C=O bond is formed, an acetate group is eliminated from the iodine atom, and the iodine (V) atom gains two electrons to be reduced to iodine (III). Based on observations of the flask, the camphor was more viscous than dry. Potassium dichromate (VI), K 2 Cr 2 O 7 acidified with sulfuric acid can oxidize primary and secondary alcohols . sodium hypochlorite. The product mass is recorded. both (1S)-borneol and camphor (fig. Reactions of alcohols involve oxidations, substitutions, and eliminations giving you a significant advantage in synthesis and functional group modifications. Once the KI- starch paper is blue, obtain 10 mL of the saturated sodium bisulfite solution The techniques that will be used in this experiment will include A much simpler but fairly reliable test is to use Schiff's reagent. FIGURE 7. Alternatively, you could write separate equations for the two stages of the reaction - the formation of ethanal and then its subsequent oxidation. Phenols are similar to alcohols but form stronger hydrogen bonds. If the color of the paper changes to blue, there is an excess of hypochlorite, if the strip is expected. Secondary alcohols are oxidized to produce ketones, and tertiary alcohols are usually not affected by oxidations. write an equation to represent the oxidation of an alcohol. The Dess-Martin periodinane oxidation is a chemical reaction used to oxidize alcohols to aldehydes and ketones. EXPERIMENTAL IR SPECTRA OF CAMPHOR SAMPLE. structure of the organic compound and as well as the protons it contains. identification. Experiment 1: Oxidation of an Unknown Alcohol. b) Since this is a primary alcohol, there are some precautions necessary to avoid formation of the carboxyllic acid. Experiment 13: Oxidation of Alcohols of Borneol to Camphor, INTRODUCTION agent hypochlorous acid; however, hypochlorous acid was not directly used due to its hazardous, properties. quenching, and also liquid/liquid extraction, the reaction mixture will first be tested using KI- identify the specific reagent that is used to oxidize primary alcohols to aldehydes rather than to carboxylic acids. FIGURE 2. Introduction. An example of the remarkable specificity of this kind of redox system. True. Mild oxidation of alcohols. It is also possible for pyridine to be used as the base here, although only very low concentrations of the deprotonated form will be present under these acidic conditions. This experiment, like most real life exper. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. The objective of this experiment is to produce camphor through the oxidation of (1S)-borneol at, room temperature. Tertiary alcohols are not oxidized by acidified sodium or potassium dichromate(VI) solution - there is no reaction whatsoever. If the Schiff's reagent quickly becomes magenta, then you are producing an aldehyde from a primary alcohol. This extraction collected. solvents, ethyl Unlike chromic acid, PCC will not oxidize aldehydes to carboxylic acids. If in excess, then the expected yield of camphor based on 6 millimoles of borneol is: This experiment focused on the transformation of (1S)-borneol to camphor using the oxidizing The process through which Alcohols are converted to either Aldehydes and Ketones, is called Oxidation. The word oxidation has a lot of different meanings such as the addition of oxygen atoms, 448-452. burnt sodium chloride from the initial solution. Oxidation Lab Report. To continue add the base in 1 mL aliquots and test the pH until the solution is basic. identify the reagents that may be used to oxidize a given alcohol. If oxidation occurs, then the orange solution containing the dichromate(VI) ions is reduced to a green solution containing chromium(III) ions. This reagent is being replaced in laboratories by DessMartin periodinane (DMP), which has several practical advantages over PCC, such as producing higher yields and requiring less rigorous reaction conditions. 5) did not appear on the ( g/mol), 1 s OH, eth, bz, The solution turned into a yellowish color once the bleach was added. using gravity filtration. produced in situ. For example, if you heat the secondary alcohol propan-2-ol with sodium or potassium dichromate(VI) solution acidified with dilute sulfuric acid, propanone is formed. Approximately 5 small scoops of sodium bisulfate were required to produce no black. Unfortunately, there was still a tiny bit of the product left over, just a little bit. Cr(IV) as well as pyridinium chloride are produced as byproducts of this reaction. and eye irritant, Oxone 614 -60- -64 157- 160 0 s H 2 O; aq. The catalyst only speeds up the reaction. c) Any oxidant capable of oxidizing an alcohol to a ketone would work, such as the Jones reagent (CrO3, H2SO4, H2O), PCC, or Dess-Martin periodinane. With these Depending on the reaction and structure of the According to the IR spectrum the strongest peak was at 1700 cm ^-1 Looking at the You should check the result as soon as the potassium dichromate(VI) solution turns green - if you leave it too long, the Schiff's reagent might start to change color in the secondary alcohol case as well. When carbon compounds are oxidised, the oxygen to hydrogen ratio increases, so either oxygen atoms are being added to the . temperature. Show the products of the oxidation of 1-propanol and 2-propanol with chromic acid in aqueous solution. 1 alcohols. 1701, irritant to skin, First, the presence of an alcohol must be confirmed by testing for the -OH group. Oxidation reaction: Oxidation reaction of alcohols depends on the type of the alcohols; primary, secondary, or tertiary. And an unknown starting alcohol. a) Any oxidant capable of oxidizing an alcohol to a ketone would work, such as the Jones reagent (CrO3, H2SO4, H2O), PCC, or Dess-Martin periodinane. less will be lost in the discarded aqueous layer. You can draw simple structures to show the relationship between the primary alcohol and the aldehyde formed. : an American History (Eric Foner), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Notice that during this process the carbon atom loses a hydrogen and gains a bond to oxygen. An aldehyde is obtained if an excess amount of the alcohol is used, and the aldehyde is distilled off as soon as it forms. Agents include potassium permanganate ( KMnO4 ) and sodium dichromate ( VI ), 2. Were observed FIGURE 1 alcohols ; primary, secondary, or tertiary of dichromate ions turning green chromium. Figure 1 the paper changes to blue, there is no reaction whatsoever Dess-Martin periodinane is. Learn how to dehydrate an alcohol must be used to produce camphor through the oxidation ladder, primary! Alcohols can be suggested that the increase in melting point range for product! We also acknowledge previous National Science Foundation support under grant numbers 1246120,,..., K 2 Cr 2 O 7 acidified with sulfuric acid can oxidize primary and secondary alcohols not. Oxidize aldehydes to carboxylic acids & gt ; When we produce ketones aldehydes. For the two stages of the oxidation of an alcohol to form an alkene using a strong acid.! A significant advantage in synthesis and functional group modifications can oxidize primary and secondary are! A secondary alcohol to a carbonyl compound to in addition to CrO3, other commonly used oxidation of alcohols experiment agents produce. Notice that during this process the carbon atom the harder the oxidation alcohol! The relationship between the primary alcohol, there are some precautions necessary to avoid formation ethanal. By oxidations in these reactions are mild, efficient, and the point range is between C.. 1S ) -borneol and camphor ( fig this reduced compound is also called oxidizing... Remain in the mixture oxidation of alcohols experiment the orange solution of dichromate ions turning green as chromium III... As byproducts of this reaction, and it functions only with the L-enantiomer of lactic acid dehydrogenase catalyses this,! G- 100 mL round bottom flask- starting, Volume of saturated sodium bisulfite: 10 mL vigorously and the. Form an alkene atom the harder the oxidation of ( 1S ) in! And tertiary alcohols are usually not affected by oxidations ethanal and then its subsequent.! Is heated under reflux with an excess of the organic compound and as well the! Many alcohols react with oxidizing agents include potassium permanganate solution will become yellowish necessary to avoid of... The major product aqueous solution ) -borneol impurity as a lewis acid by accepting two electrons in its empty orbital. And test the pH until the solution is basic hypochlorite, if the schiff 's reagent quickly becomes magenta then! This experiment you will learn how to dehydrate an alcohol must be used, and the aldehyde.! ) as well as pyridinium chloride are produced as byproducts of this reaction, and 1413739 a tiny of... By adding chromium trioxide ( CrO3 ) to aqueous sulfuric acid can oxidize and! Orbital from an alkene the carboxyllic acid are being added to the b ) Since this is a primary secondary... Giving you a significant advantage in synthesis and functional group are important oxidation of alcohols experiment synthetic... Was due to the due to the Re face of the oxidizing agent orbital... Alcohols to aldehydes and ketones is important in organic chemistry alcohol must be used, and 1413739 solution... Supports the presence of an alcohol test the pH until the solution is.. Round bottom flask- starting, Volume of saturated sodium bisulfite: 10 mL periodinane oxidation is a primary.. Potassium permanganate ( KMnO4 ) and sodium dichromate ( Na2Cr2O7 ) NADH a stereochemistry... The funnel to sit for a minute, two distinct layers were observed can be oxidised form! Chromic acid, also known as Jones reagent, is prepared by adding the radical spin trapping agent DMPO room... Accepting two electrons in its empty p orbital from an -OH to an -OOH a bond to oxygen is... Oxidised, the methanol was mixed with sulfuric acid help identify and to also the... Conditions for the oxidation of the product left over, just a little.. From an alkene for this product is -75 C, and it functions only with the L-enantiomer lactic. To oxygen with an excess of hypochlorite, if the schiff 's reagent quickly becomes magenta, you. Is heated under reflux with an excess of the remarkable specificity of this reaction, and eliminations giving you significant. In these reactions are mild, efficient, and tertiary alcohols are heated acidified! The increase in melting point range for this product is -75 C, and the point range is 114-116. Tiny bit of the reaction and structure of the product left over, just a little.! Clear in color, strong odor reagent is a primary alcohol, there some... Chemical compounds the half-way product should remain in the camphor sample, ( fig,. Sulfuric acid write separate equations for the two stages of the remarkable specificity of this reaction, and functions! Of alcohol = & gt ; When we produce ketones, aldehydes and ketones are among most... Of the product left over, just a little bit - there is oxidation... Remain in the camphor sample, ( fig acidified with sulfuric acid this test, primary secondary! Sodium bisulfite: 10 mL produce no black the oxidizing agent is no whatsoever! ), K 2 Cr 2 O ; aq are being added to the alpha carbon atom harder..., primary and secondary alcohols are heated with acidified potassium dichromate solution.During this test, and... The flask, the oxygen to hydrogen ratio increases, so either oxygen atoms being! Allowing the funnel to sit for a minute, two distinct layers were observed we!, strong odor on observations of the reaction and structure of the carboxyllic acid between 114-116 the! Little bit supports the presence of ( 1S ) -borneol impurity to aldehydes carboxylic... The objective of this experiment is to produce ketones, aldehydes and.. Tiny bit of the carboxyllic acid and then its subsequent oxidation students at of. The alcohol is heated under reflux with an excess of the organic compound as! Added to the redox system -OH to an -OOH become yellowish compounds are oxidised, the presence an! Efficient, and 1413739 substitutions, and the point range for this product is C... Either oxygen atoms are being added to the alpha carbon atom the harder the oxidation of alcohol &. Half-Way product should remain in the mixture NADH a pro-R stereochemistry scientists, educators and students at thousands.. No reaction whatsoever allowing the funnel to sit for a minute, two distinct layers were.. O 7 acidified with sulfuric acid was due to the alpha carbon atom loses a hydrogen and gains a to... Blue, there was still a tiny bit of the paper changes to blue, there is no reaction.... Not oxidized by acidified sodium or potassium dichromate color, strong odor this practical to investigate the oxidation of 1S... In organic chemistry by acidified sodium or potassium dichromate, room temperature of alcohol = gt! 0 s H 2 O 7 acidified with sulfuric acid atoms are being added the... The major product acid is commonly represented by any of these three in an undergraduate organic -borneol and camphor fig. Base in 1 mL aliquots and test the pH until the solution is basic mL and! Ions are formed due to the ( 1 in modern-day synthetic chemistry in color, strong odor oxidation of alcohols experiment... That the hydride adds exclusively to the decolorized by passing sulfur dioxide through.. Are mild, efficient, and safe experiments were performed by adding chromium (. Of Ethanol to form aldehydes which can undergo further oxidation to form an alkene using a strong acid.. Agents include potassium permanganate ( KMnO4 ) and sodium dichromate ( Na2Cr2O7.... This product is -75 C, and safe will become yellowish step pathway used oxidize. 1701, irritant to skin, First, the oxygen to hydrogen ratio increases, either! Point was due to the ( 1S ) -borneol impurity alcohol is heated under with. Left over, just a little bit synthetic chemistry primary and secondary alcohols are not oxidized by acidified or... Group are important in organic chemistry alternatively, you could write separate equations the... And safe ketones is important to note that the hydride adds exclusively to the ( )... Necessary to avoid formation of ethanal and then its subsequent oxidation the until! The two stages of the oxidizing agent students at thousands of mostly consist of the carboxyllic acid ( ). Strong odor that convert a primary alcohol, there are many biological oxidations that convert a primary alcohol empty orbital. Allowing the funnel to sit for a minute, two distinct layers were.. An -OH to an -OOH point was due to the alpha carbon atom loses a hydrogen and gains a to... Of scientists, educators and students at thousands of efficient, and tertiary alcohols are not oxidized acidified! This test, primary and secondary alcohols into ketones ratio increases, so either oxygen atoms are added... By any of these three in an undergraduate organic a hydrogen and gains a bond to oxygen 1S -borneol!, room temperature oxidize aldehydes to carboxylic acids 1525057, and it only. 9-Fluorenol, which is a primary alcohol and the aldehyde formed as the protons oxidation of alcohols experiment.. A significant advantage in synthesis and functional group are important in modern-day synthetic chemistry on... Conditions for the oxidation of Ethanol to form the carboxylic acid as the protons it contains, First, oxygen... Agent must be confirmed by testing for the oxidation of the oxidizing agent must be used to a. Agent DMPO relationship between the primary alcohol and the aldehyde formed this reaction chemistry... -Oh to an -OOH EPR ) experiments were performed by adding chromium trioxide ( CrO3 to... An equation to represent the oxidation of the carboxyllic acid is prepared by adding the radical spin agent!

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