Experiment 3: Preparation of Lidocaine
|
|
- Tracy Pearson
- 5 years ago
- Views:
Transcription
1 Experiment 3: Preparation of Lidocaine This two-step synthesis involves the following conversion: 2,6-dimethylaniline α- chloro-2, 6-dimethylacetanilide Lidocaine. This synthetic scheme is shown in equation (1). Each step is discussed in more detail in each individual part of the lab along with experimental procedures. verall Reaction Sequence: NH 2 + C 2 H N H 2,6-dimethylaniline!-chloroacetyl chloride!-chloro-2,6-dimethylacetanilide ( CH 2 ) 2 NH diethylamine (1) N H N Lidocaine 1
2 Experiment Part A: Preparation of α-chloro-2, 6- dimethylacetanilide from 2,6-dimethylaniline. INTRDUCTIN 2, 6-Dimethylaniline is converted to α-chloro-2, 6-dimethylacetanilide by allowing it to react with α-chloroacetyl chloride, as shown in equation (2). NH 2 + C 2 H N H (2) 2,6-dimethylaniline!-chloroacetyl chloride!-chloro-2,6-dimethylacetanilide The nitrogen atom in 2, 6-dimethylaniline is a nucleophile because of the non-bonding pair of electrons on nitrogen. Nucleophilic substitution occurs selectively at the acyl carbon atom in α-chloroacetyl chloride because of the greater reactivity of nucleophiles toward acid chlorides compared to alkyl chlorides. The reasons for this selectivity are attributed to the differences in the electrophilicity of the two carbon atoms in α- chloroacetyl chloride. Electronically, the carbonyl carbon has two electron-withdrawing groups the oxygen doubly bonded to it and the - bonded to it. n the other hand, the carbon in CH 2 has only one electron-withdrawing group (-). Besides electronics, steric factors also play a role in this selectivity. It is easier for the nucleophile to attack the carbon of the planar carbonyl group in the acid chloride than to attack the tetrahedral carbon in the CH 2 group. The mechanism for the substitution reaction that occurs between an amine and an acid chloride may be found in lecture textbooks and may be discussed by your instructor. This reaction is carried out in glacial (anhydrous) acetic acid as the solvent. The acetic acid reacts with 2, 6-dimethylaniline to establish an equilibrium between it and its acetate salt, as shown in equation (3a) on the following page. As the reaction proceeds, hydrochloric acid is liberated so that 2, 6-dimethylaniline is partially converted into its hydrochloride salt [equation (3b)]. If this salt remains at the end of the reaction, it would contaminate the α-chloro-2, 6-dimethylacetanilide because both the hydrochloride salt and the α-chloro-2, 6-dimethylacetanilide are insoluble in cold acetic acid. The co-precipitation is avoided by adding an aqueous solution of sodium acetate to the warm reaction mixture and plays two key roles. (a) It reestablishes the reaction 2
3 shown in equation (3a) as an acid-base equilibrium. Sodium acetate, which is the salt of the weak acid acetic acid, serves to remove the H that is formed in the reaction and yield acetic acid, as shown in equation (3c) and to prevent co-precipitation of the hydrochloride salt. (b) The addition of the water contained in the aqueous sodium acetate solution changes the polarity of the solvent and causes the α-chloro-2, 6- dimethylacetanilide to precipitate. NH 2 + CH NH 3 C (3a) acetate salt NH 2 + H- NH 3 (3b) hydrochloride salt C + H- CH + acetate anion acetic acid (3c) Vacuum filtration is used to collect the product. The acetate salt of 2, 6- dimethylaniline and unreacted 2, 6-dimethylaniline are soluble in water and thus remain in the filtrate. After collecting the α-chloro-2, 6-dimethylacetanilide product by vacuum filtration, it is washed with several portions of cold water to remove residual amounts of acetic acid, unreacted 2, 6-dimethylaniline and the acetate salt of 2, 6- dimethylaniline. The α-chloro-2, 6-dimethylacetanilide is allowed to air-dry until the next lab period at which point a weight will be obtained. If desired, it can then converted without further purification to lidocaine in experiment 3B. 3
4 REAGENT/PRDUCT TABLE: Reagents MW (g/mol) MP (ºC) BP (ºC) Density 2, 6-dimethylaniline /739mm alpha-chloroacetyl chloride acetic acid Product alpha-chloro-2, 6-dimethylacetanilide MW (g/mol) EXPERIMENTAL PRCEDURE FR YUR SAFETY 1. α-chloroacetyl chloride is a noxious chemical and must be kept in the hood. When it is used, transfer it to the conical vial in the hood (Step 3). 2. Wear gloves at all times when handling α-chloroacetyl chloride. 3. Avoid inhaling α-chloroacetyl chloride. 1. Heat a 0-mL beaker containing about 40 ml of water and a couple of boiling stones on the hot plate set to about 3 until the water is gently boiling. This beaker will be used as a hot water bath. 2. Take a clean, dry, pre-weighed ml conical vial with spin vane with a cap and add 0.0 ml of 2, 6-dimethylaniline (density g/ml) to the vial. Reweigh this capped vial to determine the weight of 2, 6-dimethylaniline you added to it. Add about 1 ml of glacial acetic acid to the same vial. Stir this mixture gently with the tip of a clean microspatula, to ensure the contents in the vial are mixed. 3. btain a clean dry small sample vial with a cap and take a weight on them. In the hood, place 0.0 ml of α-chloroacetyl chloride (density = 1.42 g/ml) in the vial, cap it and and reweigh to determine the weight of the α-chloroacetyl chloride you added. [Note: You must transfer the α-chloroacetyl chloride to this vial in the hood.] Add about 1 ml of glacial acetic acid to this vial, and stir this mixture gently with the tip of a clean microspatula, to ensure mixing. 4. Take the ml conical vial containing 2,6-dimethylaniline/glacial acetic acid mixture to the hood, and using a dry pipette, transfer the α-chloroacetyl chloride/glacial acetic acid mixture to the ml conical vial. Attach an air condenser to the conical vial, clamp the air condenser and lower the conical vial so it is about one-half immersed in the hot water bath. (See Section A.3 and Figure A.3) Start magnetic stirring, and after the water starts to boil, continue heating for about 30 minutes. 4
5 Safety Note: Place the small sample vial that had contained the α chloroacetyl chloride/glacial acetic acid in the dirty vial beaker in the hood.. After heating the reaction mixture in the conical vial for 30 minutes, cool it to room temperature by placing the conical vial (air condenser still attached) in a beaker of cold tap water. In the hood, remove the air condenser and pour the contents of the reaction vial into a clean, dry 30-mL beaker. Add about 6. ml (measured with a graduated cylinder) of 0.4 M NaAc at one time to the beaker. This causes the α chloro-2, 6-dimethylacetanilide to form as a heavy precipitate. Stir the mixture with a stirring rod, and cool the beaker in an ice water bath for about minutes. 6. Collect the solid by vacuum filtration using a Hirsch funnel (see Section A.2, Figure A.2). Add about 1 ml of ice water to the beaker that contained the reaction mixture and pour it over the solid on the filter to wash the 2, 6-product. Add a second 1 ml portion of ice water to the funnel. Keep the vacuum applied to the filter flask and filter containing the solid for about 10 minutes to remove as much solvent as possible. Break up the solid on the funnel with a clean, microspatula and leave the funnel containing your product in a small beaker in your locker to dry until the next lab period. At that time, you will need to get a weight on your compound and record this in your notebook. No melting point will be taken on this product. WASTE DISPSAL Place the filtrate contained in the filter flask in the aqueous acid waste bottle.
6 %Transmittance Wavenumbers (cm-1) Date: Wed Dec 16 10:44: (GMT-0:00) 2,6-dimethylaniline Scans: 4 Resolution: 4.000
7 %Transmittance Wavenumbers (cm-1) Date: Wed Dec 16 10:49: (GMT-0:00) alpha-chloroacetyl chloride Scans: 4 Resolution: 4.000
8 NH PPM
9 N H PPM
Expt 6: Preparation of Lidocaine, Part 1
Expt 6: Preparation of Lidocaine, Part 1 Local anesthetics are an important class of clinical drugs that provide targeted numbing and pain relief when applied to specific areas of the body. This is in
More information2 (CH 3 CH 2 ) 2 NH diethylamine
Experiment: (Part B) Preparation of Lidocaine from α-chloro-2,6-dimethylacetanilide and Diethylamine ITRDUCTI This step of the synthesis involves the reaction of α-chloro-2, 6- dimethylacetanilide, prepared
More informationExpt 8: Preparation of Lidocaine, Part 2, from α- Chloro-2,6-dimethylacetanilide and Diethylamine
Expt 8: Preparation of Lidocaine, Part 2, from α- Chloro-2,6-dimethylacetanilide and Diethylamine ITRDUCTI This step of the synthesis involves the reaction of α-chloro-2, 6-dimethylacetanilide, prepared
More informationExpt 9: The Aldol Condensation
Expt 9: The Aldol Condensation INTRDUCTIN Reactions that form carbon-carbon bonds are particularly important in organic chemistry as they allow the synthesis of more complex structures from simpler molecules.
More informationExpt 7: Preparation of Isobutyl Propionate (or Isobutyl Propanoate)
Expt 7: Preparation of Isobutyl Propionate (or Isobutyl Propanoate) INTRDUCTIN Esters are an important class of carbonyl compounds that are formally derived by combining a carboxylic acid and an alcohol.
More informationExperiment 1: Preparation of Vanillyl Alcohol
Experiment 1: Preparation of Vanillyl Alcohol INTRDUCTIN A common method for preparing alcohols is the reduction of aldehydes to form primary alcohols [equation (1)] or of ketones to produce secondary
More informationExpt 10: Friedel-Crafts Alkylation of p-xylene
Expt 10: Friedel-Crafts Alkylation of p-xylene INTRODUCTION The Friedel-Crafts alkylation reaction is one of the most useful methods for adding alkyl substituents to an aromatic ring. Mechanistically,
More informationExpt 5: Synthesis of Benzoic Acid Using the Grignard Reaction
Expt 5: Synthesis of Benzoic Acid Using the Grignard Reaction INTRDUCTIN The Grignard reaction is one of the most general methods for carbon-carbon bond formation in all of organic chemistry. In the first
More informationExperiment 12: Grignard Synthesis of Triphenylmethanol
1 Experiment 12: Grignard Synthesis of Triphenylmethanol Reactions that form carbon-carbon bonds are among the most useful to the synthetic organic chemist. In 1912, Victor Grignard received the Nobel
More informationExperiment 7: The Synthesis of Artificial Hyacinth Odor (1-bromo-2-phenylethene), Part I
Experiment 7: The Synthesis of Artificial Hyacinth Odor (1-bromo-2-phenylethene), Part I This two-step synthesis involves the following conversion: trans-cinnamic acid 2,3- dibromocinnamic acid 1-bromo-2-phenylethene
More informationReview Experiments Formation of Polymers Reduction of Vanillin
Review Experiments Formation of Polymers What is a polymer? What is polymerization? What is the difference between an addition polymerization and a condensation polymerization? Which type of polymerization
More informationExperiment 17 Preparation of Methyl Orange
Experiment 17 Preparation of Methyl range In this experiment you will prepare methyl orange, an azo dye that forms beautiful orange crystals and is used as an acid-base indicator (Figure 17.1). The anion
More informationChemistry 283g Experiment 4
Chemistry 283g xperiment 4 XPRIMNT 4: lectrophilic Aromatic Substitution: A Friedel-Craft Acylation Reaction Relevant sections in the text: Fox & Whitesell, 3 rd d. Chapter 11, especially pg. 524-526,
More informationExperiment 3: Acid/base Extraction and Separation of Acidic and Neutral Substances
Experiment 3: Acid/base Extraction and Separation of Acidic and Neutral Substances Introduction Your task in this lab is to separate two compounds by taking advantage of differences in their acidity, and
More informationThe Synthesis of Triphenylmethano. will synthesize Triphenylmethanol, a white crystalline aromatic
HEM 333L rganic hemistry Laboratory Revision 2.0 The Synthesis of Triphenylmethano ol In this laboratory exercise we will synthesize Triphenylmethanol, a white crystalline aromatic compound. Triphenylmethanol
More informationSodium Borohydride Reduction of Benzoin
Sodium Borohydride Reduction of Benzoin Introduction The most common and useful reducing agents for reducing aldehydes, ketones, and other functional groups are metal hydride reagents. The two most common
More informationGRIGNARD REACTION Synthesis of Benzoic Acid
1 GRIGNARD REACTION Synthesis of Benzoic Acid In the 1920 s, the first survey of the acceleration of chemical transformations by ultrasound was published. Since then, many more applications of ultrasound
More informationNucleophilic displacement - Formation of an ether by an S N 2 reaction The Williamson- Ether Synthesis
Nucleophilic displacement - Formation of an ether by an S N 2 reaction The Williamson- Ether Synthesis Bond formation by use of an S N 2 reaction is very important for organic and biological synthesis.
More informationTo understand concept of limiting reagents. To learn how to do a vacuum filtration. To understand the concept of recrystallization.
E x p e r i m e n t Synthesis of Aspirin Experiment : http://genchemlab.wordpress.com/-aspirin/ objectives To synthesize aspirin. To understand concept of limiting reagents. To determine percent yield.
More informationExperiment 11: Dehydration of Cyclohexanol
Experiment 11: Dehydration of yclohexanol INTRODUTION In this experiment, cyclohexanol is dehydrated by aqueous sulfuric acid to produce cyclohexene as the sole product [equation (1)], and no rearrangement
More informationExperiment V: Multistep Convergent Synthesis: Synthesis of Hexaphenylbenzene
Experiment V: Multistep Convergent Synthesis: Synthesis of Hexaphenylbenzene 1) Introduction CH H Thiamine HCl (V-02) ah (aq) Cu(Ac) 2 H 4 3 HAc V-01 V-03 V-04 Me 3 + H - V-05 V-06 Tetraphenylcyclopentadieneone
More informationSynthesis of Benzoic Acid
E x p e r i m e n t 5 Synthesis of Benzoic Acid Objectives To use the Grignard reagent in a water free environment. To react the Grignard reagent with dry ice, CO 2(s). To assess the purity of the product
More informationExp t 144 Synthesis of N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF"
Exp t 144 Synthesis of,-diethyl-m-toluamide: The Insect epellent "FF" Adapted by. Minard and Sridhar Varadarajan from Introduction to rganic Laboratory Techniques: A Microscale Approach, Pavia, Lampman,
More informationAldol Condensation Notes
Reminder: These notes are meant to supplement, not replace, the laboratory manual. Aldol Condensation Notes History and Application Condensation reactions are molecular transformations that join together
More informationThe Friedel-Crafts Reaction: 2-(4-methylbenzoyl)benzoic acid
The Friedel-Crafts Reaction: 2-(4-methylbenzoyl)benzoic acid Exp t 63 from K. L. Williamson, Macroscale and Microscale rganic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston. p449 revised 10/13/98
More informationORG1 Syntheses of Acetaminophen and Aspirin
RG1 Syntheses of Acetaminophen and Aspirin Estimated Time Required: 60 minutes Introduction Ethanoylation (better known as acetylation) is the introduction of an acetyl functional group onto a suitable
More informationExperiment 3. Condensation Reactions of Ketones and Aldehydes: The Aldol Condensation Reaction.
Experiment 3. Condensation Reactions of Ketones and Aldehydes: The Aldol Condensation Reaction. References: Brown & Foote, Chapters 16, 19, 23 INTRODUCTION: This experiment continues the saga of carbon-carbon
More informationAspirin Synthesis H 3 PO 4
Aspirin Synthesis Experiment 10 Aspirin is the common name for the compound acetylsalicylic acid, widely used as a fever reducer and as a pain killer. Salicylic acid, whose name comes from Salix, the willow
More information5: SYNTHESIS OF TRIS(ETHYLENEDIAMINE)NICKEL(II) CHLORIDE
Experiment 5: SYNTHESIS OF TRIS(ETHYLENEDIAMINE)NICKEL(II) CHLORIDE Purpose: Synthesize a nickel(ii) complex and apply reaction stoichiometry to determine the percent yield Performance Goals: Prepare a
More informationChemical Reactions: The Copper Cycle
1 Chemical Reactions: The Copper Cycle ORGANIZATION Mode: pairs assigned by instructor Grading: lab notes, lab performance and post-lab report Safety: Goggles, closed-toe shoes, lab coat, long pants/skirts
More informationScheme 1. Outline in the acid-base extraction of Bengay, hydrolysis to salicylic acid, and esterification to synthesize aspirin.
Experiment 6 Synthesis of Aspirin, Lab Practical Exam Preparation Students come to lab with a pen/pencil, calculator, and pre-lab questions (no notebook). Students will carry out the experiment individually;
More informationPreparation of an Ester Acetylsalicylic Acid (Aspirin)
Preparation of an Ester Acetylsalicylic Acid (Aspirin) BJECTIVE: To become familiar with the techniques and principle of esterification. DISCUSSIN: Aspirin is a drug widely used as an antipyretic agent
More informationCHEMISTRY Organic Chemistry Laboratory II Spring 2019 Lab #2: Grignard Reaction: Preparation of Triphenylmethanol
CHEMISTRY 244 - Organic Chemistry Laboratory II Spring 2019 Lab #2: Grignard Reaction: Preparation of Triphenylmethanol Purpose. In this lab you will use the Grignard Reaction, a classic reaction in organic
More informationFlushing Out the Moles in Lab: The Reaction of Calcium Chloride with Carbonate Salts
Flushing Out the Moles in Lab: The Reaction of Calcium Chloride with Carbonate Salts Pre-lab Assignment: Reading: 1. Chapter sections 3.3, 3.4, 3.7 and 4.2 in your course text. 2. This lab handout. Questions:
More informationEXPERIMENT: LIMITING REAGENT. NOTE: Students should have moles of reactants in DATASHEET converted into masses in grams prior to the lab period.
Revised 12/2015 EXPERIMENT: LIMITING REAGENT Chem 1104 Lab NOTE: Students should have moles of reactants in DATASHEET converted into masses in grams prior to the lab period. INTRODUCTION Limiting reactant
More information12AL Experiment 9: Markovnikov s Rule
12AL Experiment 9: Markovnikov s Rule Safety: Proper lab goggles/glasses must be worn (even over prescription glasses). WEAR GLOVES this lab utilizes hydrogen peroxide which can burn your skin and multiple
More informationExperiment 7 - Preparation of 1,4-diphenyl-1,3-butadiene
Experiment 7 - Preparation of 1,4-diphenyl-1,3-butadiene OBJECTIVE To provide experience with the Wittig Reaction, one of the most versatile reactions available for the synthesis of an alkene. INTRODUCTION
More information6. Extraction. A. Background. (a) (b) (c) Figure 1. Mixing of Solvents
6. Extraction A. Background Extraction is a frequently used technique to selectively transfer a compound of interested from one solvent to another. Extraction is based on solubility characteristics of
More information12BL Experiment 7: Vanillin Reduction
12BL Experiment 7: Vanillin Reduction Safety: Proper lab goggles/glasses must be worn (even over prescription glasses). WEAR GLOVES and please handle the following chemicals with care: Hydrochloric acid
More informationCHEMISTRY Organic Chemistry Laboratory II Spring 2019 Lab #3: Friedel-Crafts Acylation
CHEMISTRY 244 - Organic Chemistry Laboratory II Spring 2019 Lab #3: Friedel-Crafts Acylation Purpose: In this lab you will predict and experimentally test the directing effects of substituent groups in
More informationLisa Barton CHEM 2312 Organic Chemistry Performed: 2/4/12. Synthesis of Aspirin
Lisa Barton CHEM 2312 rganic Chemistry Performed: 2/4/12 Synthesis of Aspirin bjective: The goal of this experiment is to synthesize Aspirin (Acetylsalicylic Acid) from the reaction of Salicylic acid and
More information2. Synthesis of Aspirin
This is a two-part laboratory experiment. In part one, you will synthesize (make) the active ingredient in aspirin through a reaction involving a catalyst. The resulting product will then be purified through
More informationCl 2(g) + NaCl + H 2 O. light. 2Cl. Once formed, the chlorine radical can react with the heptane as shown below: + Cl
Experiment Free Radical Chlorination of Heptane In today s experiment, you will be chlorinating n-heptane with chlorine atoms (radicals) to form monochlorination products of that alkane. You will analyze
More informationExperiment 24. Chemical recycling of poly(ethylene) terephthalate (PET)
Methods of pollution control and waste management Experiment 24 Chemical recycling of poly(ethylene) terephthalate (PET) Manual Department of Chemical Technology The aim of this experiment is to gain knowledge
More informationAcid Anhydrides CH3 C. ethanoic anhydride.
arboxylic acid derivatives: Acyl hlorides and Acid Anhydrides Acyl hlorides l ethanoyl chloride Acyl chlorides are much more reactive than carboxylic acids Acid Anhydrides ethanoic anhydride. Acid anhydrides
More informationExperiment 9: Synthesis and Isolation of Optical Isomers of a Cobalt (III) Compound CH3500: Inorganic Chemistry, Plymouth State University
Experiment 9: Synthesis and Isolation of Optical Isomers of a Cobalt (III) Compound CH3500: Inorganic Chemistry, Plymouth State University Adapted from GS Girolami, TB Rauchfuss, RJ Angelici, "Experiment
More information12AL Experiment 11 (3 days): Nucleophilic Substitution Reactions
12AL Experiment 11 (3 days): Nucleophilic Substitution Reactions Instructor note: Day 1 (half of the class); Day 2 (other half); Day 3 (everyone to finish up any separation & purification steps etc). Initial
More information6. Extraction. A. Background. (a) (b) (c) Figure 1. Mixing of Solvents
6. Extraction A. Background Extraction is a frequently used technique to selectively transfer a compound of interested from one solvent to another. Extraction is based on solubility characteristics of
More informationAP Chemistry Lab #5- Synthesis and Analysis of Alum (Big Idea 1 & 2)
www.pedersenscience.com AP Chemistry Lab #5- Synthesis and Analysis of Alum (Big Idea 1 & 2) 1.A.1: Molecules are composed of specific combinations of atoms; different molecules are composed of combinations
More informationSYNTHESIS OF 1-BROMOBUTANE Experimental procedure at macroscale (adapted from Williamson, Minard & Masters 1 )
SYNTHESIS OF 1-BROMOBUTANE Experimental procedure at macroscale (adapted from Williamson, Minard & Masters 1 ) Introduction 1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced
More informationSPECIFICATION & TEST PROCEDURE SODIUM SALICYLATE Technical. Molecular weight : Reference : In-house
Page 1 of 8 Molecular Formula : C 7 H 5 NaO 3 CAS Registry No. : [54 21 7] Molecular weight : 160.10 Reference : In-house Other names : Benzoic acid, 2 hydroxy, mono sodium salt, Mono sodium salicylate.
More informationExperiment 8 Synthesis of Aspirin
Experiment 8 Synthesis of Aspirin Aspirin is an effective analgesic (pain reliever), antipyretic (fever reducer) and anti-inflammatory agent and is one of the most widely used non-prescription drugs. The
More informationR C OR' H 2 O carboxylic acid alcohol ester water side product
EXPERIMENT 7 SYNTHESIS OF ESTERS USING ACETIC ANHYDRIDE 1 Materials Needed 2.0 ml of an alcohol to be chosen from the following: 1-propanol (n-propyl alcohol), 3-methyl 1-butanol (isoamyl alcohol, isopentyl
More informationGeneral Chemistry I CHEM-1030 Laboratory Experiment No. 2 Physical Separation Techniques
General Chemistry I CHEM-1030 Laboratory Experiment No. 2 Physical Separation Techniques Introduction When two or more substances that do not react chemically are blended together, the components of the
More informationCH 241 EXPERIMENT #6 WEEK OF NOVEMBER 12, NUCLEOPHILIC SUBSTITUTION REACTIONS (S N 1 and S N 2)
C 241 EXPERIMENT #6 WEEK OF NOVEMBER 12, 2001 NUCLEOPILIC SUBSTITUTION REACTIONS (S N 1 and S N 2) Background By the time you do this experiment we should have covered nucleophilic substitution reactions
More informationReductive Amination Reaction
Boston University OpenBU Chemistry http://open.bu.edu Organic Chemistry Laboratory Experiments 2011-07-14 eductive Amination eaction Mulcahy, Seann P. https://hdl.handle.net/2144/1419 Boston University
More informationLab #3 Reduction of 3-Nitroacetophenone
Lab #3 Reduction of 3-Nitroacetophenone Introduction: Extraction: This method uses a different technique in which the two chemical compounds being separated are in immiscible solvents, also known as phases.
More informationmedia), except those of aluminum and calcium
1- Aspirin occurs as white crystals or as a white crystalline powder. 2- It is slightly soluble in water (1:300), soluble in alcohol (1 :5), chloroform (1:17) & ether (1:15). It dissolves easily in glycerin.
More informationAcid-Base Extraction
Experiment: Acid-Base Extraction Background information on the theory of extraction is covered extensively online and will also be covered in your discussion The information here pertains specifically
More informationThe Grignard Reaction: Synthesis of 1,2-diphenyl-1,2-propanediol via a Diastereoselective Reaction.
EXPERIMENT 2 The Grignard Reaction: Synthesis of 1,2-diphenyl-1,2-propanediol via a Diastereoselective Reaction. Relevant sections in the text: Fox & Whitesell, 3 rd Ed. pg. 400-404, 615-618 General Concepts
More informationWittig Reaction. Mulcahy, Seann P. Boston University Boston University
Boston University penbu Chemistry http://open.bu.edu rganic Chemistry Laboratory Experiments 2012-01-03 Wittig Reaction Mulcahy, Seann P. https://hdl.handle.net/2144/2688 Boston University The Wittig Reaction
More informationScheme 2: Formation of Di- Halide via Chloronium Intermediate
Bromination of Alkenes CHM226 Background The carbon- carbon double bond, also known as an alkene, is a very important functional group in organic chemistry, and is often used as a precursor in the synthesis
More informationMinneapolis Community and Technical College. Separation of Components of a Mixture
Minneapolis Community and Technical College Chemistry Department Chem1020 Separation of Components of a Mixture Objectives: To separate a mixture into its component pure substances. To calculate the composition
More informationSeparation and Identification of Metal Ions
Vivek Kumar, Ph.D. OBJECTIVES: In this experiment, you will analyze an aqueous solution for the presence of Ag +, Pb 2+ and Hg2 2+ ions LEARNING GOALS 1. To understand and apply chemistry of metal ions
More informationExp t 111 Structure Determination of a Natural Product
Exp t 111 Adapted by R. Minard, K. Smereczniak and Jon Landis (Penn State Univ.) from a microscale procedure used by the University of California, Irvine, in its undergraduate labs. The procedure is based
More informationExperimental techniques
Experimental techniques 2.1 Measurement Apparatus used in the lab: Name Use Picture Beaker Used to hold liquids Burette Used to add accurate volumes of liquid Conical Flask Used to hold liquids Crystallizing
More informationCHEMISTRY Organic Chemistry Laboratory II Spring 2019 Lab #1: Oxidation of Alcohols to Ketones - Borneol Oxidation (2 weeks)
CHEMISTRY 244 - Organic Chemistry Laboratory II Spring 2019 Lab #1: Oxidation of Alcohols to Ketones - Borneol Oxidation (2 weeks) Purpose. In this lab you will learn about oxidation reactions in organic
More informationINTRODUCTION TO MICROSCALE ORGANIC CHEMISTRY
INTRODUCTION TO MICROSCALE ORGANIC CHEMISTRY Welcome to the world of microscale organic chemistry. Most of the experiments you will perform this semester will be done on a small scale with specially designed
More informationHonors Cup Synthetic Proposal
onors Cup Synthetic Proposal Section: 270-V Group Members: Azhar Carim, Ian Cross, Albert Tang Title: Synthesis of indigo from -(2-bromoethyl)-2-nitrobenzamide Introduction: Indigo has been used as a dye
More informationGreen Chemistry in the Undergraduate Organic Laboratory: Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay
LAB PRCEDURE: Green Chemistry in the Undergraduate rganic Laboratory: Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay Matthew R. Dintzner*, Paul R. Wucka and Thomas
More information5. SEPARATION OF MIXTURES, PURIFICATION OF SOLIDS Objectives
Name: Date:.. 5. SEPARATION OF MIXTURES, PURIFICATION OF SOLIDS Objectives Introduction to basic chemical laboratory operations: grinding, dissolving, decanting, centrifuging, filtration, crystallization.
More informationLab #6: CARBOXYLIC ACIDS LAB
lab Lab #6: CARBOXYLIC ACIDS LAB Name PART I: Preparation of Carboxylic Acids (a) Oxidation of an Aldehyde by Oxygen from the Air: Benzaldehyde is an aromatic aldehyde with a familiar odor. On a clean,
More informationChlorobenzene from Aniline via the Sandmeyer Reaction. August 21, By ParadoxChem126. Introduction
Chlorobenzene from Aniline via the Sandmeyer Reaction August 21, 2014 By ParadoxChem126 Introduction Chlorobenzene is a useful chemical in organic syntheses. It dissolves a wide range of organic compounds,
More informationR R CH. Some reactions of alcohols vary depending on their classification as 1º, 2º, or 3º alcohols.
Experiment: Alcohol Reactions Alcohols are important organic molecules characterized by an alkyl group covalently bonded to a hydroxyl group. They may be classified as primary, secondary, or tertiary,
More informationExperiment : Reduction of Ethyl Acetoacetate
Experiment 7-2007: eduction of Ethyl Acetoacetate EXPEIMENT 7: eduction of Carbonyl Compounds: Achiral and Chiral eduction elevant sections in the text: Fox & Whitesell, 3 rd Ed. Chapter 12, pg.572-584.
More information18 Macroscale and Microscale Organic Experiments
360465-P01[01-024] 10/17/02 16:16 Page 18 Sahuja Ahuja_QXP_03:Desktop Folder:17/10/02: 18 Macroscale and Microscale Organic Experiments Preparing a Laboratory Record Use the following steps to prepare
More information22. The Diels-Alder Cycloaddition Reaction
22. The Diels-Alder Cycloaddition Reaction A. Introduction In 1928, tto Diels and his student Kurt Alder at the University of Kiel in Germany first reported their work in the reactions of electron poor
More information26. The preparation and purification of N-phenylethanamide Student Sheet
26. The preparation and purification of N-phenylethanamide Student Sheet In this experiment you will learn or develop skills in preparative organic chemistry by making and purifying a sample of an aromatic
More informationArenediazonium Ions in Organic Synthesis: Para Red and para-iodonitrobenzene
Arenediazonium Ions in Organic Synthesis: Para Red and para-iodonitrobenzene Background An arenediazonium salt will be prepared from para-nitroaniline and used in two different reactions with iodide ion
More informationFriedel-Crafts Reaction
OpenStax-CNX module: m15260 1 Friedel-Crafts Reaction Mary McHale This work is produced by OpenStax-CNX and licensed under the Creative Commons Attribution License 2.0 1 Lab 4: Friedel-Crafts Reaction:
More informationWavenumbers. Infrared spectrum of 6-ethoxycarbonyl-3,5-diphenyl-2-cyclohexenone, KBr. Enamine Reactions: 2-Acetylcyclohexanone
33 Part Three Properties and Reactions of Organic Compounds I QUESTIONS 1. Why was it possible to separate the product from sodium hydroxide using acetone? 2. The white solid that remains in the centrifuge
More informationSYNTHESIS OF AN AZO DYE revisited (1 or 2 credits)
SYNTHESIS OF AN AZO DYE revisited (1 or 2 credits) This lab you can revisit the fist experiment of this quarter and synthesize more azo dyes of your choice. The old procedure is given below followed by
More informationExperiment 17. Synthesis of Aspirin. Introduction
Experiment 17 Introduction Synthesis of Aspirin Aspirin (acetylsalicylic acid) is a synthetic organic derived from salicylic acid. Salicylic acid is a natural product found in the bark of the willow tree
More informationUniversity of Wisconsin Chemistry 116 Preparation and Characterization of Aspirin and Some Flavoring Esters *
University of Wisconsin Chemistry 116 Preparation and Characterization of Aspirin and Some Flavoring Esters * Esters are an important class of organic compounds commonly prepared via a condensation reaction
More informationLab 2. Go Their Separate Ways: Separation of an Acid, Base, and Neutral Substance by Acid-Base Extraction
Lab 2. Go Their Separate Ways: Separation of an Acid, Base, and Neutral Substance by Acid-Base Extraction How can I use an acid-base reaction to separate an acid-base-neutral mixture? Objectives 1. use
More informationThe CCLI Initiative Computers in Chemistry Laboratory Instruction
Experiment Determining the Coordination Number of Ni and Cu The CCLI Initiative Computers in Chemistry Laboratory Instruction by Enthalpy The objectives of this experiment are to... LEARNING OBJECTIVES
More informationLimiting Reagent Synthesis of Aspirin Thomas M. Moffett Jr., SUNY Plattsburgh, 2007.
Limiting Reagent Synthesis of Aspirin Thomas M. Moffett Jr., SUNY Plattsburgh, 007. Aspirin (acetylsalicylic acid) is the most common medicinal drug in use today. Aspirin is an analgesic (pain reliever),
More informationLab Activity 3: Gravimetric Stoichiometry 2
Chemistry 2202 Gravimetric Stoichiometry Lab 2 1 Lab Activity 3: Gravimetric Stoichiometry 2 Introduction: Stoichiometry involves making predictions about how much of one substance should react or be produced
More informationScientific Observations and Reaction Stoichiometry: The Qualitative Analysis and Chemical Reactivity of Five White Powders
Scientific Observations and Reaction Stoichiometry: The Qualitative Analysis and Chemical Reactivity of Five White Powders Objectives Part 1: To determine the limiting reagent and percent yield of CuCO
More informationEXPERIMENT 6. Physical and Chemical Changes Part 2 INTRODUCTION
EXPERIMENT 6 Physical and Chemical Changes Part 2 INTRODUCTION Evidence of chemical change can be the evolution of heat or light, the formation of a gas (seen in Experiment 5), the appearance of a material
More informationExperiment 3 Two-Step Synthesis of Ionones
Experiment 3 Two-Step Synthesis of Ionones Reading: Mohrig Section 24 (UV-vis Spectroscopy), Palleros p. E23B.1-3 (included here) * Students will work with one lab partner (no groups of three) Notebook
More informationNucleophilic Addition to Carbonyl: Grignard Reaction with a Ketone
Experiment 7 Nucleophilic Addition to Carbonyl: Grignard eaction with a Ketone prepared by Jan William Simek, California Polytechnic State University modified by Hyunwoo Kim, Sunkyu Han and Eunyoung Yoon,
More informationEXPERIMENT 20. Solutions INTRODUCTION
EXPERIMENT 20 Solutions INTRODUCTION A solution is a homogeneous mixture. The solvent is the dissolving substance, while the solute is the dissolved substance. A saturated solution is one in which the
More informationFree Radical Chlorination
Free Radical Chlorination Although saturated hydrocarbons are inert to most acidic and basic reagents, they can be halogenated in the presence of a free radical initiator. The process is a chain reaction,
More informationPrelab Assignmet Date, Title, Introduction. You will complete the procedures during the lab period as you plan for each test.
1 Qualitative Analysis Prelab Assignmet Date, Title, Introduction. You will complete the procedures during the lab period as you plan for each test. Introduction In this experiment you will be determining
More informationExperiment 8: Chlorination of 1-Chlorobutane
1 Experiment 8: Chlorination of 1-Chlorobutane Alkanes contain only nonpolar carbon-hydrogen and carbon-carbon single bonds, which makes them unreactive toward most acidic and basic reagents. They can,
More informationExperiment 12 Grignard Reaction; Preparation of Triphenylcarbinol
Experiment 12 Grignard Reaction; Preparation of Triphenylcarbinol In this experiment we will perform a Grignard addition to an ester. First we will form the Grignard reagent from magnesium and bromobenzene
More informationThe Synthesis and Analysis of Aspirin
The Synthesis and Analysis of Aspirin Computer 22 Aspirin, the ubiquitous pain reliever, goes by the chemical name acetylsalicylic acid. One of the compounds used in the synthesis of aspirin is salicylic
More informationExp't 141. Exp't 141
Exp't 141 Exp't 141 Chlorination of 1-Chlorobutane from K L Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed 1994, Houghton Mifflin, Boston p255, Rev 10/13/98 Prelab exercise: If there
More information12BL Experiment 1: The Diels-Alder Reaction
12BL Experiment 1: The Diels-Alder Reaction Safety: Proper lab goggles/glasses must be worn (even over prescription glasses). As always, ask where organic waste containers are located in the lab. Background:
More information