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M.Sc (ORGANIC CHEMISTRY) LABORATORY MANUAL

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M.Sc (ORGANIC CHEMISTRY) LABORATORY MANUAL DEPARTMENT OF CHEMISTRY RAJA BAHADUR VENKATA RAMA REDDY WOMEN’S COLLEGE (Autonomous) Affiliated to Osmania University Accredited by NAAC with ‘A’ Grade College with Potential for Excellence (Selected by UGC) Narayanaguda, Hyderabad, Telangana State SYNTHESIS OF ORGANIC COMPOUNDS INDEX S. No Contents Page No. 1. Synthesis of Organic Compounds 1-31 2. Multi step synthesis of Organic Compounds 35-77 3. Isolation of Natural Products 79-85 4. Synthesis of Drugs 87-107 5. Separation of Organic binary & ternary mixtures 109-115 6. Qualitative Analysis of Organic Compounds 117-135 7. Spectral Analysis of Unknown Organic compounds 137-145 8. Chromatography 147-166 9. Estimation of Drugs 167-201 10. Microwave Assisted Organic Synthesis 202 CONTENTS 1. ACETANILIDE 2. P-BROMO ACETANILIDE 3. P-BROMO ANILINE 4. 2,4,6-TRIBROMO ANILINE 5. ASPIRIN 6. HIPPURIC ACID 7. TETRA-HYDRO CARBAZOLE 8. PHTHALIMIDE 9. META-DINITRO BENZENE 10. META NITRO ANILINE 11. ANTHRACENE-MALEIC ANHYDRIDE ADDUCT 12. 2,4- DIHYDROXY ACETOPHENONE 13. 7-HYDROXY-4-METHYL COUMARIN 14. AZALACTONE Department of Chemistry, RBVRRWC 1 2017-2018 ACETANILIDE General Reaction O NH2 NH C CH3 O O CH3COOH CH COOH O 3 Aniline Acetic Anhydride Acetanilide Mechanism O O O O C C NH2 H2N CH CH O O 3 3 O O H O C NH C CH3 H3C N H C O CH3 CH3COOH Acetanilide Department of Chemistry, RBVRRWC 2 2017-2018 PREPARATION OF ACETANILIDE Aim: To study N-acylation. Principle: Aniline undergoes N-acylation with acetic anhydride in the presence of glacial acetic acid, preferentially attacking the nitrogen atom of aniline. Reaction:N-acylation / N-acetylation / Electrophilic Substitution Reaction. Chemicals: Aniline - 5mL Glacial acetic acid - 5mL Acetic anhydride - 5mL Apparatus: R. B. Flask, Beaker, Water condenser. Procedure: Transfer 5mLof Aniline into a clean & dry round bottomed flask, add 5mL of glacial acetic acid and 5mL of acetic anhydride. Add a porcelain piece and fix the water condenser and boil the mixture for 15 minutes on bunsen flame. Test for the completion of reaction by transferring a few drops of mixture into a beaker containing 100mL of cold water. If white precipitate is formed, it indicates that the reaction is completed. If no precipitate is formed continue heating for 10 more minutes and check for completion of the reaction.Then transfer the reaction mixture into beaker containing cold water & stir with a glass rod. Filter the compound under suction. Wash the precipitate with cold water & dry the sample. Recrystallisation: Solvent-Hot water M.P: 1140C Department of Chemistry, RBVRRWC 3 2017-2018 Department of Chemistry, RBVRRWC 4 2017-2018 PREPARATION OF P-BROMO ACETANILIDE Aim: To study the orientation of Electrophilic Substitution Reaction. Principle: Aniline undergoes electrophilic substitution with bromine at 2, 4, 6 – positions to form tribromo aniline. To substitute selectively, the amino group has to be protected by acylation such that the bulky group restricts electrophilic substitution at ortho position because of steric hindrance & directs to para position. Reaction : Electrophilic Substitution Reaction. Chemicals: Acetanilide – 4gms Glacial CH3COOH – 10mL Bromine in glacial CH3COOH – 10mL Apparatus: Conical flask, beaker &glass rod Procedure: Dissolve 4gms of finely powdered acetanilide in 10mL of cold glacial acetic acid in a 250mL conical flask. In another small flask take 10mL of bromine in acetic acid and add this solution slowly into acetanilide solution until reddish orange colour persists. Shake the reaction mixture throughout the addition to ensure thorough mixing. Allow the final mixture to stand at room temperature for 15 minutes with occasional stirring. Then pour the reddish orange solution which may already contain some crystals of p-bromo acetanilide into a large amount of cold water, where upon p-bromo acetanilide will readily crystallizes out. Stir these crystals thoroughly with water to eliminate CH3COOH & wash it with cold water & filter. Recrystallisation: Solvent-Rectified Spirit M.P: 163oC Department of Chemistry, RBVRRWC 5 2017-2018 Department of Chemistry, RBVRRWC 6 2017-2018 PREPARATION OF P-BROMO ANILINE Aim: To study hydrolysis of p-bromo acetanilide Principle: p-bromo acetanilide undergoes hydrolysis in the presence of conc.HCl to form p-bromo aniline. Reaction: Hydrolysis (deacylation) Chemicals: Para bromo acetanilide – 4gms Conc HCl-5mL Ethyl alcohol – 8mL 5% NaOH Apparatus: R.B. flask, water condenser Procedure: Dissolve 4g of p-bromo acetanilide in 8mL of boiling ethanol contained in a 100mL round bottomed flask. Add 5mL of conc. HCl drop wise to the boiling solution. Reflux for 30-40 minutes. Dilute the reaction mixture with 50mL of water where by p-bromo aniline is formed. Neutralize the acidic solution with 5% NaOH until alkaline. Para bromo aniline separates as oil, which crystallizes by adding ice and filter. Recrystallisation: Solvent-Alcohol M.P: 66oC Department of Chemistry, RBVRRWC 7 2017-2018 2,4,62,4,6 -T TRIBROMORIBROMO A NANILINEILINE General reaction NH NH2 2 Br Br CH3COOH 3 Br2 Mechanism Br Formation of Electrophile O O H3C C OH H3C C O H Br Br H H Br Br Electrophile Formation of Sigma Complex NH2 NH2 NH2 NH2 NH2 Resonance hybrid Attack of Electrophile NH 2 NH2 NH2 NH2 Br H Br H Br Br Br NH2 NH NH 2 NH2 2 Br H Br Br Br Br Br Br Br NH2 Br NH2 NH2 Br H Br Br Br Br Br Br Br 2,4,6-TRIBROMO ANILINE 2,4,6 Tribromo aniline Department of Chemistry, RBVRRWC 8 2017-2018 PREPARATION OF 2, 4, 6–TRIBROMO ANILINE Aim: To study Electrophilic Substitution Reaction (bromination) on aniline Principle: Aniline readily undergoes Electrophilic Substitution Reaction by involving the non-bonding electrons present on nitrogen. As NH2group is Ortho& Para directing and also ring activating group there is an increase in electron density at ortho and para positions. Therefore aniline on bromination gives 2,4,6- tribromo aniline (i.e) bromination takes place at 2,4&6 positions. Reaction:Electrophilic Substitution Reaction (Bromination) Chemicals: Aniline – 5mL Acetic acid – 19mL Bromine in CH3COOH – 30mL. Apparatus: Beaker, Funnel, Measuring jar, Glass rod. Procedure: Take 5mL of aniline and 19mL ofglacial acetic acid in conical flask & keep this flask in ice bath and then add 30mL of Br2in acetic acid drop wise with constant stirring till orange colour of bromine persists. Allow the solution to stand at room temp for 15 minutes. Pour it into the cold water. 2,4,6-tribromo aniline precipitates out and filter. Recrystallisation: Solvent- Ethyl Alcohol M.P: 1200C Department of Chemistry, RBVRRWC 9 2017-2018 ASPIRIN General Reaction O OH O C CH COOH 3 O O COOH Conc. H2SO4 CH3COOH O Salicylic Acid Acetic Anhydride Aspirin Mechanism H O O O O H O O H O O H O O O H O OH HO O O HOOC HOOC HOOC CH3COOH - H O O C CH3 COOH Aspirin Department of Chemistry, RBVRRWC 10 2017-2018 PREPARATION OF ASPIRIN Aim: To prepare aspirin by O-acylation Principle: Salicylic acid undergoes acetylation with acetic anhydride selectively at the weakly acidic group (i.e.) phenolic group into strongly acidic group in the presence of conc. H2SO4as catalyst. Reaction: Electrophilic Substitution Reaction /O-Acetylation / O-Acylation Chemicals: Salicylic acid – 2gms Acetic anhydride– 2.8mL Conc.H2SO4- 2-3 drops Apparatus: Conical flask, glass rod. Procedure: Weigh about 2gms of salicylic acid and transfer into a clean conical flask and add 2.8mL of acetic anhydride and stir it with a glass rod and add 2-3 drops of conc. H2SO4 and stir the mixture and warm on water bath to about 50-60oC for 15 minutes. Allow the mixture to cool and add about 50mL of water. Stir well and filter at the pump. Recrystallisation: Solvent-Equal amounts of acetic acid and water M.P:1360C Department of Chemistry, RBVRRWC 11 2017-2018 -HCl HIPPURIC ACID Genearal reaction O O O Cl NaOH H2N H OH N O Benzoyl Chloride H Glycine Hippuric Acid O Mechanism O NaOOC CH2 O O O NaOH Ph Cl HN C Ph H2N NH2 OH H2O NaO H Cl -HCl CH2COONa O O HOH H HN C N NaOH HO O Hippuric Acid Department of Chemistry, RBVRRWC 12 2017-2018 PREPARATION OF HIPPURIC ACID Aim: To study N-Benzoylation Principle: Electrophilic substitution of benzoyl group on nitrogen atom of glycine gives N-Benzoyl glycine, commonly known as Hippuric acid. Reaction: N-Benzoylation of glycine. Chemicals: Glycine - 2.5gm 10% NaOH – 2.5mL Benzoyl chloride – 4.5mL Apparatus: Conical flask, glass rod,cork Procedure: Dissolve 2.5 gms of glycine in 2.5mL of 10% NaOH solution taken in a conical flask (if not dissolved add few more mL of 10% NaOH) and add 4.5mL of benzoyl chloride in two portions to the solution. Stopper the flask and shake vigorously after each addition. Transfer the solution into a beaker containing water & filter it. If product is not formed, add crushed ice. Recrystallisation: Solvent – Boiling water M.P: 1870C Department of Chemistry, RBVRRWC 13 2017-2018 TETRA HYDRO CARBAZOLE General Reaction AcOH NH NH2 O N H Phenyl Hydrazene Cyclohexanone Tetra Hydro Carbazole Mechanism Ph Ph H NH N Ph NH NH2 HN N O H H O HO -H2O H H H N N HN N H H Ph H H H NH3 NH HN N H H2N N H Tetra Hydro Carbazole Department of Chemistry, RBVRRWC 14 2017-2018 PREPARATION OF TETRA – HYDRO CARBAZOLE Aim: To study Fischer Indole synthesis. Principle: Fischer Indolization occurs when phenyl hydrazine reacts with saturated cyclic aldehyde or ketone. Cyclization takes place with loss of NH3 under the influence of reagents like glacial acetic acid. Phenyl hydrazine of saturated cyclic ketone like cyclohexanone undergoes cyclisation very rapidly when boiled with glacial acetic acid.
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    02/22/13 COMMONWEALTH OF PENNSYLVANIA DEPARTMENT OF ENVIRONMENTAL PROTECTION BUREAU OF POINT AND NON-POINT SOURCE MANAGEMENT RATIONALE FOR THE DEVELOPMENT OF AMBIENT WATER QUALITY CRITERIA RESORCINOL & SULFONIC ACID COMPOUNDS (Revised February 2012) (Revised February 2013) Introduction: Beazer East, Inc. (Beazer) implemented environmental investigations and remediation at sites in Butler and Armstrong Counties, Pennsylvania in cooperation with the Department of Environmental Protection (Department) and United States Environmental Protection Agency (U.S. EPA). These sites are located within an area approximately 60 square miles in size that has been designated by the Department under the Hazardous Sites Cleanup Act (HSCA) as the “Bear Creek Area Chemical Site” (BCACS). The Department has determined that environmental media (i.e. soil and groundwater) within the BCACS have been impacted by sulfonate (sulfonic acid) compounds and resorcinol and other hazardous substances. The sulfonic acid compounds include meta-benzene disulfonic acid (m-BDSA), benzene monosulfonic acid (BSA), p-phenol sulfonic acid (p-PSA). Currently, with respect to surface water, there are no ambient water quality criteria for the sulfonic acids or resorcinol, which are needed to evaluate the environmental clean-up objectives and progress within the BCACS. EPA and Department Review Aquatic Life Water Quality Criteria Developed by AMEC: Because water quality criteria had not been developed for the sulfonic acids or resorcinol by either the Department or the U.S. EPA, AMEC Earth & Environmental (AMEC) used U.S. EPA's national guidelines to develop aquatic life water quality criteria (Stephan, et al., 1985) in accordance with 25 Pa. Code § 16.22. (AMEC. April 2008).
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    Vienna International Centre, P.O. Box 500, 1400 Vienna, Austria Tel: (+43-1) 26060-0, Fax: (+43-1) 26060-5866, www.unodc.org RECOMMENDED METHODS FOR THE IDENTIFICATION AND ANALYSIS OF AMPHETAMINE, METHAMPHETAMINE AND THEIR RING-SUBSTITUTED ANALOGUES IN SEIZED MATERIALS (revised and updated) MANUAL FOR USE BY NATIONAL DRUG TESTING LABORATORIES Laboratory and Scientific Section United Nations Office on Drugs and Crime Vienna RECOMMENDED METHODS FOR THE IDENTIFICATION AND ANALYSIS OF AMPHETAMINE, METHAMPHETAMINE AND THEIR RING-SUBSTITUTED ANALOGUES IN SEIZED MATERIALS (revised and updated) MANUAL FOR USE BY NATIONAL DRUG TESTING LABORATORIES UNITED NATIONS New York, 2006 Note Mention of company names and commercial products does not imply the endorse- ment of the United Nations. This publication has not been formally edited. ST/NAR/34 UNITED NATIONS PUBLICATION Sales No. E.06.XI.1 ISBN 92-1-148208-9 Acknowledgements UNODC’s Laboratory and Scientific Section wishes to express its thanks to the experts who participated in the Consultative Meeting on “The Review of Methods for the Identification and Analysis of Amphetamine-type Stimulants (ATS) and Their Ring-substituted Analogues in Seized Material” for their contribution to the contents of this manual. Ms. Rosa Alis Rodríguez, Laboratorio de Drogas y Sanidad de Baleares, Palma de Mallorca, Spain Dr. Hans Bergkvist, SKL—National Laboratory of Forensic Science, Linköping, Sweden Ms. Warank Boonchuay, Division of Narcotics Analysis, Department of Medical Sciences, Ministry of Public Health, Nonthaburi, Thailand Dr. Rainer Dahlenburg, Bundeskriminalamt/KT34, Wiesbaden, Germany Mr. Adrian V. Kemmenoe, The Forensic Science Service, Birmingham Laboratory, Birmingham, United Kingdom Dr. Tohru Kishi, National Research Institute of Police Science, Chiba, Japan Dr.