CH421 Experiment 2. Nitration of Aniline: a three-step protecting group strategy to prepare p-nitroaniline
|
|
- Shona Thompson
- 7 years ago
- Views:
Transcription
1 CH421 Experiment 2 Nitration of Aniline: a three-step protecting group strategy to prepare p-nitroaniline Reading: Organic Chemistry by John McMurry, 8e, Chapter Techniques: recrystallization, melting point, IR, NMR Introduction Electrophilic aromatic substitution is one of the more common ways to functionalize aromatic rings, and one common method is nitration. The reactivity of the aromatic ring is heavily influenced by substituent effects, specifically resonance and/or inductive effects of the substituent. The purpose of this experiment is to prepare para-nitroaniline from aniline. Para-nitroaniline is used in the synthesis of the dye para red (aka American flag red). One of the intermediates in our synthetic scheme, acetanilide, was also used in the synthesis of sulfanilamide, one of the first synthetic antibiotics. We will perform the synthesis of para-nitroaniline over several steps (overall scheme shown below): acetylation of aniline to form acetanilide; nitration of acetanilide, which forms a mixture of ortho- (minor) and para-nitroacetanilide (major); and hydrolysis of the nitroacetanilides to liberate ortho- and para-nitroanilines. Separation of the ortho- and para-nitroanilines is accomplished by recrystallization. When performing multi-step synthesis, high yield is important, since each reaction uses as starting material the product of the previous reaction. For example, if in three successive reactions the yields are: 80%, 90%, and 75% respectively, the overall yield at the end of the third reaction is 0.8 x 0.9 x 0.75 x 100 = 54%. For this reason, multi-step syntheses are a good test of laboratory skills. In the first step of the sequence above, aniline is acetylated with acetic anhydride to produce acetanilide. Note that the desired final product in this experiment is a mono-nitroaniline. Why, then, is the step of acetylating the aniline included in the reaction scheme? Essentially, the amide is used as a protecting group for the aniline in this scheme (keep in mind amines can act as bases and nucleophiles; amides in contrast are non-basic, non-nucleophilic). First, aniline can be oxidized by nitric acid. (If aniline and nitric acid are mixed directly, a violent oxidation of the aniline occurs which can cause the mixture to ignite.) In addition, under these acidic reaction conditions, aniline is protonated, and the anilinium cation is actually a meta-director! Thus, in order to successfully and selectively mononitrate aniline at the para position, it is necessary to modify the amine as the amide, perform the nitration reaction, and remove the acetamide protecting group at the end of the synthesis the liberate the amine. The second step in our sequence is the nitration of acetanilide. Nitronium ion (NO 2 + ) is a very strong electrophile that is generated in situ from concentrated nitric acid and sulfuric acid, as shown below.
2 In the mechanism of this reaction, the nucleophilic pi electrons on the aromatic ring attack the electrophile NO 2 +. The resulting intermediate carbocation is short-lived, since aromaticity is lost upon addition of NO 2 +. Elimination of the paraproton restores aromaticity, resulting in an overall substitution reaction. In electrophilic aromatic substitutions where there is an electron-donating group (EDG, such as OMe) on the aromatic ring, the electrophile substitutes in the ortho- and/or para- positions relative to the EDG. This is due to resonance stabilization of the intermediate carbocation by the EDG. On the other hand, if there is an electron-withdrawing group (EWG) on the aromatic ring, reaction is directed to the meta position. In this reaction, the electrophile substitutes mainly at the position para to the acetanilide, since the amide is an electron-donating group (EDG) by resonance. While we want to obtain the p-nitroacetanilide selectively, in reality we obtain a mixture of isomers, wherein p- nitroacetanilide is the major isomer (see scheme below). Acetanilide displays moderate reactivity in electrophilic aromatic substitution as it is a weak EDG. Also, unlike aniline, acetanilide is not oxidized by nitric acid. Nitration of acetanilide gives principally the ortho and para mononitroacetanilides (with more para than ortho due to sterics), together with a small amount of 2,4-dinitroacetanilide. To prevent dinitration of the acetanilide, the nitrating mixture of concentrated nitric acid and sulfuric acids is added in small portions to the acetanilide solution (and not vice versa), so that the concentration of the nitrating agent is kept at a minimum. The nitroacetanilides are not isolated in this reaction scheme. Instead, the reaction mixture is heated and the acid present serves to hydrolyze them to the nitroanilines (see scheme below). Separation of the para- and ortho-nitroanilines is effected by recrystallization in ethanol due to the different solubility of each compound in ethanol. In Week 1, we will prepare acetanilide (Step 1), isolate it, and fully characterize the crude product. In Week 2, we will perform two steps: nitration of acetanilide (Step 2), followed by hydrolysis of the acetamide (Step 3) to generate the desired nitroaniline product.
3 Safety Precautions Nitrobenzene, aniline, and nitroaniline are toxic; aniline is also a cancer suspect agent. Sulfuric acid, nitric acid, acetic anhydride, and ammonium hydroxide are extremely caustic; avoid skin contact. If contact does occur, flush with water for 15 minutes. Wear your gloves and protective clothing throughout this experiment and work in the fume hood to avoid breathing vapors. Week 1: Preparation of Acetanilide Pre-Lab Notebook (to be completed prior to the start of lab in Week 1) Enter date, experiment number and title on notebook page and in TOC with corresponding page number. Copy the Week 1 reaction and the reaction table below (in your own writing) into your notebook and complete all empty cells in the table. Make sure to check your calculations with your instructor before starting the experiment. Name formula MW (g/mol) mass (g) mmol equiv d (g/ml) vol (ml) mp ( C) bp ( C) aniline C 6 H 7 N acetic anhydride C 4 H 6 O water H 2 O desired rxn conc M 1.0 acetanilide C 8 H 9 NO Lit. mp Week 1 Procedure Into a 125-mL Erlenmeyer flask, weigh out 1.50 g of aniline (NOTE: always record the actual mass that you measured to the precision of your balance), add a stir bar, and dissolve this in enough water to give a concentration of 0.27 M (you should record the VOLUME of water used). Add 1.2 equivalents of acetic anhydride, and stir the solution at room temperature for at least minutes. At some point, solids should form. Note any changes that occur to the reaction mixture and the times at which they occurred. After minutes, cool the reaction mixture in an ice bath to complete crystallization. Isolate the product by vacuum filtration, wash it with cold water, and allow it to dry on the funnel by pulling air through the solids for 20 minutes. It is imperative that your acetanilide be dry for the next step! Thus, label a small beaker, obtain a tare weight, and put your produce in it covered with a Kimwipe/rubber band to dry in the back of the hood for a week.
4 Data for Week 1 (collect and record in your notebook during the lab) Describe product and calculate crude % yield of the dried solid Obtain melting point and list with literature value Obtain IR (solid is best), staple in notebook, and assign major functional group peaks Obtain 1 H NMR (use ~10 mg in CDCl 3 ), staple into notebook, and assign all peaks in the spectrum Record beaker tare weights Week 2: a) Nitration of Acetanilide; b) Hydrolysis of Nitroacetanilides Pre-Lab Notebook (to be completed prior to the start of lab in Week 2) Enter date, experiment number and title on notebook page and in TOC with corresponding page number. Copy the Week 2 reaction and the reaction table below (in your own writing) into your notebook and complete all empty cells in the table. Make sure to check your calculations with your instructor before starting the experiment. HN O 1.H 2 SO 4,HNO 3 2.H 2 O,heat 3.NH 4 OH NH 2 acetanilide NO 2 p-nitroaniline Name formula MW (g/mol) mass (g) mmol equiv d (g/ml) vol (ml) mp ( C) bp ( C) acetanilide C 8 H 9 NO conc. H 2 SO 4 H 2 SO conc. HNO 3 HNO conc. NH 4 OH NH 4 OH 33.9 p-nitroaniline C 6 H 6 N 2 O 2 Lit. mp
5 Week 2 Procedure Measure 8 equivalents of concentrated sulfuric acid into a 10-mL graduated cylinder (this volume should be in your notebook, as you calculated it previously). Pour about half of this acid into a 50-mL round bottom flask. To the acid remaining in the graduated cylinder, add 2.0 equivalents of concentrated nitric acid (again, record volume). Carefully mix the two acids in the cylinder by filling a Pasteur pipet at the bottom of the cylinder, and then discharging it at the top, several times. Add 0.90 g of your dry acetanilide from Week 1 to the sulfuric acid in the Erlenmeyer flask, swirl until almost all of it has dissolved, and then cool the flask in an ice bath. Using a Pasteur pipet, transfer about ¼ ml portions of the nitric-sulfuric acid mixture to the flask and swirl the flask in the ice bath after each addition. Do not allow the flask to become warm; the addition of all of the mixture of acids should require about 10 min. When the addition of acids is complete, swirl for 2 minutes, then add to the reaction mixture 10 ml of ice water and a boiling chip. Attach a water-cooled condenser to the flask. Using a heating mantle as the heat source (Variac setting ~ 70), gently boil the mixture for 15 min to effect hydrolysis of the nitroacetanilides. Cool the flask in an ice bath. When the reaction mixture is thoroughly cold (make sure it and the ice bath are directly under your hood), CAUTIOUSLY add a total of 9 ml of concentrated ammonium hydroxide in approximately 1 ml portions, taking care to swirl the flask after each addition. Make sure that the mouth of the flask is not pointed at yourself or your neighbor. This neutralization reaction is quite exothermic, and if done improperly, it will result in a sudden evolution of ammonia that expels the contents out of the flask! Collect the crude product by vacuum filtration, wash the product in the Büchner funnel with a total of 4 ml of cold water, and dry it by drawing air through it for 5-10 minutes. Run a TLC of your crude product in 1:1 hexanes:ethyl acetate, draw the plate in the Data section and calculate Rf s for all spots. The crude product contains both ortho- and para-nitroaniline. As stated in the introduction to this experiment, the major isomer is para-nitroaniline. (The amount of dinitroaniline present is negligible.) Recrystallize the crude product from about 2 ml of hot ethanol in a 25-mL Erlenmeyer flask. Allow the mixture to slowcool to room temperature, and then set it in an ice bath for min. Isolate the resulting solids by vacuum filtration use 1-2 ml of cold ethanol to transfer remaining crystals to the funnel and to rinse the crystals on the filter paper. Dry the solids by pulling air through the funnel for 10 minutes. Run TLC of your purified product in 1:1 hexanes:ethyl acetate, draw the plate and calculate Rf in your Data section. Data for Week 2 (collect and record in your notebook during the lab) Describe product and calculate % yield of the recrystallized solid TLC data (draw crude and purified product TLC s, calculate Rf s, include mobile phase) Obtain melting point and list with literature value Obtain IR (solid is best), staple in notebook, and assign major functional group peaks Obtain 1 H NMR (use ~10 mg in CDCl 3 ), staple into notebook, and assign all peaks in the spectrum Overall Conclusion (record in your notebook) State outcome, yield for each step, overall yield for the two steps, proof of success and purity, possible sources of error, and any other information deemed necessary and relevant (i.e. spectral data as support). Also note how well recrystallization went (should compare TLC of crude vs. purified product).
6 The IR and NMR data for your aniline starting material are given below for your reference. IR of aniline (thin film) 1H NMR of aniline (90 MHz in CDCl 3 ) s, 2H m, 2H m, 3H
Online edition for students of organic chemistry lab courses at the University of Colorado, Boulder, Dept of Chem and Biochem.
u Experiment 9 Aromatic Chemistry: Synthesis of o-nitroaniline and p-nitroaniline via a Multi-Step Sequence Reading: Introduction to rganic Chemistry by Streitwieser, Heathcock, and Kosower, pp. 695-696
More informationEXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate
EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate Pahlavan/Cherif Purpose a) Study electrophilic aromatic substitution reaction (EAS) b) Study regioselectivity
More informationexperiment5 Understanding and applying the concept of limiting reagents. Learning how to perform a vacuum filtration.
81 experiment5 LECTURE AND LAB SKILLS EMPHASIZED Synthesizing an organic substance. Understanding and applying the concept of limiting reagents. Determining percent yield. Learning how to perform a vacuum
More informationEXPERIMENT 9 (Organic Chemistry II) Pahlavan - Cherif Synthesis of Aspirin - Esterification
EXPERIMENT 9 (rganic hemistry II) Pahlavan - herif Materials Hot plate 125-mL Erlenmeyer flask Melting point capillaries Melting point apparatus Büchner funnel 400-mL beaker Stirring rod hemicals Salicylic
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 informationExperiment 14 Preparation of p-nitroaniline
Experiment 14 Preparation of p-nitroaniline This experiment usually takes three weeks to complete and counts as two laboratory experiments (40 points). We will do a three-step synthesis to make p-nitroaniline
More informationSulfa Antibiotics - Synthesis of Sulfanilamide
Sulfa Antibiotics - Synthesis of Sulfanilamide INTRDUCTIN Many people think of the term chemotherapy as relating to specific modern drug treatments used to fight cancer. Actually, modern chemotherapy began
More informationCHEM 2423 Recrystallization of Benzoic Acid EXPERIMENT 4 - Purification - Recrystallization of Benzoic acid
EXPERIMENT 4 - Purification - Recrystallization of Benzoic acid Purpose: a) To purify samples of organic compounds that are solids at room temperature b) To dissociate the impure sample in the minimum
More informationSaturated NaCl solution rubber tubing (2) Glass adaptor (2) thermometer adaptor heating mantle
EXPERIMENT 5 (Organic Chemistry II) Pahlavan/Cherif Dehydration of Alcohols - Dehydration of Cyclohexanol Purpose - The purpose of this lab is to produce cyclohexene through the acid catalyzed elimination
More informationCHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon*
CHM220 Nucleophilic Substitution Lab Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* Purpose: To convert a primary alcohol to an alkyl bromide using an S N 2 reaction
More informationExperiment 5 Preparation of Cyclohexene
Experiment 5 Preparation of yclohexene In this experiment we will prepare cyclohexene from cyclohexanol using an acid catalyzed dehydration reaction. We will use the cyclohexanol that we purified in our
More informationEXPERIMENT Aspirin: Synthesis and NMR Analysis
EXPERIMENT Aspirin: Synthesis and NMR Analysis Introduction: When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is produced according
More informationSeparation by Solvent Extraction
Experiment 3 Separation by Solvent Extraction Objectives To separate a mixture consisting of a carboxylic acid and a neutral compound by using solvent extraction techniques. Introduction Frequently, organic
More informationEnantiomers: Synthesis, characterization, and resolution of tris(ethylenediamine)cobalt(iii) chloride Introduction:
Enantiomers: Synthesis, characterization, and resolution of tris(ethylenediamine)cobalt(iii) chloride Introduction: The development of coordination chemistry prior to 1950 involved the synthesis and characterization
More informationSynthesis of Aspirin and Oil of Wintergreen
Austin Peay State University Department of hemistry hem 1121 autions Purpose Introduction Acetic Anhydride corrosive and a lachrymator all transfers should be done in the vented fume hood Methanol, Ethanol
More informationExperiment 3: Extraction: Separation of an Acidic, a Basic and a Neutral Substance
1 Experiment 3: Extraction: Separation of an Acidic, a Basic and a Neutral Substance Read pp 142-155, 161-162, Chapter 10 and pp 163-173, Chapter 11, in LTOC. View the videos: 4.2 Extraction (Macroscale);
More informationPREPARATION AND PROPERTIES OF A SOAP
(adapted from Blackburn et al., Laboratory Manual to Accompany World of Chemistry, 2 nd ed., (1996) Saunders College Publishing: Fort Worth) Purpose: To prepare a sample of soap and to examine its properties.
More informationPage 1 of 5. Purification of Cholesterol An Oxidative Addition-Reductive Elimination Sequence
Page 1 of 5 Purification of Cholesterol An Oxidative Addition-Reductive Elimination Sequence From your lectures sessions in CEM 2010 you have learned that elimination reactions may occur when alkyl halides
More informationThe Synthesis of trans-dichlorobis(ethylenediamine)cobalt(iii) Chloride
CHEM 122L General Chemistry Laboratory Revision 2.0 The Synthesis of trans-dichlorobis(ethylenediamine)cobalt(iii) Chloride To learn about Coordination Compounds and Complex Ions. To learn about Isomerism.
More informationRecrystallization II 23
Recrystallization II 23 Chem 355 Jasperse RECRYSTALLIZATIN-Week 2 1. Mixed Recrystallization of Acetanilide 2. Mixed Recrystallization of Dibenzylacetone 3. Recrystallization of an Unknown Background Review:
More informationSynthesis of Isopentyl Acetate
Experiment 8 Synthesis of Isopentyl Acetate Objectives To prepare isopentyl acetate from isopentyl alcohol and acetic acid by the Fischer esterification reaction. Introduction Esters are derivatives of
More informationExtraction: Separation of Acidic Substances
Extraction: Separation of Acidic Substances Chemists frequently find it necessary to separate a mixture of compounds by moving a component from one solution or mixture to another. The process most often
More informationA Greener Synthesis of Creatine
A Greener Synthesis of Creatine Carl S Lecher 1 and Ryan J Bernhardt, 2 Marian College, Indianapolis, I Chemical Concepts Addition to nitriles, vacuum filtration, melting point determination Green Lessons
More informationHEAT OF FORMATION OF AMMONIUM NITRATE
303 HEAT OF FORMATION OF AMMONIUM NITRATE OBJECTIVES FOR THE EXPERIMENT The student will be able to do the following: 1. Calculate the change in enthalpy (heat of reaction) using the Law of Hess. 2. Find
More informationDYES AND DYEING 2003 by David A. Katz. All rights reserved. Permission for classroom use provided original copyright is included.
DYES AND DYEING 2003 by David A. Katz. All rights reserved. Permission for classroom use provided original copyright is included. Dyeing of textiles has been practiced for thousands of years with the first
More informationGeneral Chemistry I (FC, 09-10) Lab #3: The Empirical Formula of a Compound. Introduction
General Chemistry I (FC, 09-10) Introduction A look at the mass relationships in chemistry reveals little order or sense. The ratio of the masses of the elements in a compound, while constant, does not
More informationCH243: Lab 4 Synthesis of Artificial Flavorings by Fischer Esterification
H243: Lab 4 Synthesis of Artificial Flavorings by Fischer Esterification PURPSE: To prepare esters by reaction of carboxylic acids and alcohols. To modify a known procedure to prepare an unknown. DISUSSIN:
More informationSODIUM CARBOXYMETHYL CELLULOSE
SODIUM CARBOXYMETHYL CELLULOSE Prepared at the 28th JECFA (1984), published in FNP 31/2 (1984) and in FNP 52 (1992). Metals and arsenic specifications revised at the 55 th JECFA (2000). An ADI not specified
More informationEXPERIMENT 2 (Organic Chemistry II) Pahlavan/Cherif Diels-Alder Reaction Preparation of ENDO-NORBORNENE-5, 6-CIS-CARBOXYLIC ANHYDRIDE
EXPERIMENT 2 (rganic Chemistry II) Pahlavan/Cherif Diels-Alder Reaction Preparation of END-NRBRNENE-5, 6-CIS-CARBXYLIC ANYDRIDE Purpose a) Study conjugated dienes b) Study diene and dienophile c) Study
More informationBenzene Benzene is best represented as a resonance hybrid:
Electrophilic Aromatic Substitution (EAS) is a substitution reaction usually involving the benzene ring; more specifically it is a reaction in which the hydrogen atom of an aromatic ring is replaced as
More information14 Friedel-Crafts Alkylation
14 Friedel-Crafts Alkylation 14.1 Introduction Friedel-Crafts alkylation and acylation reactions are a special class of electrophilic aromatic substitution (EAS) reactions in which the electrophile is
More informationElectrophilic Aromatic Substitution
Electrophilic Aromatic Substitution Electrophilic substitution is the typical reaction type for aromatic rings. Generalized electrophilic aromatic substitution: E E Electrophile Lewis acid: may be or neutral.
More informationIsolation of Caffeine from Tea
Isolation of Caffeine from Tea Introduction A number of interesting, biologically active compounds have been isolated from plants. Isolating some of these natural products, as they are called, can require
More informationEXPERIMENT FIVE. Preparation of Cyclohexene from Cyclohexanol: an Elimination Reaction DISCUSSION
EXPERIMENT FIVE Preparation of Cyclohexene from Cyclohexanol: an Elimination Reaction DISCUSSION A secondary alcohol, such as cyclohexanol, undergoes dehydration by an E1 mechanism. The key intermediate
More informationHands-On Labs SM-1 Lab Manual
EXPERIMENT 4: Separation of a Mixture of Solids Read the entire experiment and organize time, materials, and work space before beginning. Remember to review the safety sections and wear goggles when appropriate.
More informationThe most common active ingredient used in deodorants is aluminium chlorohydrate. But not all deodorants contain aluminium chlorohydrate:
Engineeringfragrance make a deodorant practical activity 2 student instructions page 1 of 5 chemical compounds The most common active ingredient used in deodorants is aluminium chlorohydrate. But not all
More information4026 Synthesis of 2-chloro-2-methylpropane (tert-butyl chloride) from tert-butanol
4026 Synthesis of 2-chloro-2-methylpropane (tert-butyl chloride) from tert-butanol OH + HCl Cl + H 2 O C 4 H 10 O C 4 H 9 Cl (74.1) (36.5) (92.6) Classification Reaction types and substance classes nucleophilic
More informationSEPARATION OF A MIXTURE OF SUBSTANCES LAB
SEPARATION OF A MIXTURE OF SUBSTANCES LAB Purpose: Every chemical has a set of defined physical properties, and when combined they present a unique fingerprint for that chemical. When chemicals are present
More informationDistillation Experiment
Distillation Experiment CHM226 Background The distillation process is a very important technique used to separate compounds based on their boiling points. A substance will boil only when the vapor pressure
More informationoxidize 4-Cholesten-3-one
Isolation of Cholesterol from Egg Yolk Preparation: Bring a hard-boiled egg yolk to lab! Cholesterol (1) is a major component of cell membranes. An egg yolk contains about 200 milligrams of cholesterol,
More informationPhysical and Chemical Properties and Changes
Physical and Chemical Properties and Changes An understanding of material things requires an understanding of the physical and chemical characteristics of matter. A few planned experiments can help you
More informationPHYSICAL SEPARATION TECHNIQUES. Introduction
PHYSICAL SEPARATION TECHNIQUES Lab #2 Introduction When two or more substances, that do not react chemically, are blended together, the result is a mixture in which each component retains its individual
More informationph: Measurement and Uses
ph: Measurement and Uses One of the most important properties of aqueous solutions is the concentration of hydrogen ion. The concentration of H + (or H 3 O + ) affects the solubility of inorganic and organic
More informationPREPARATION OF ACETYLSALICYLIC ACID (ASPIRIN)
PREPARATIN F ACETYLSALICYLIC ACID (ASPIRIN) BACKGRUND ne of the most widely used nonprescription drugs is aspirin. In the United States, more than 15,000 pounds are sold each year. This is not surprising
More informationChemiluminescence: Synthesis of Cyalume 3 Chemiluminescence: Synthesis of Cyalume and Making it Glow
Chemiluminescence: Synthesis of Cyalume 3 Chemiluminescence: Synthesis of Cyalume and Making it Glow Intro Chemiluminescence is the process whereby light is produced by a chemical reaction. The flashes
More informationCHEMICAL REACTIONS OF COPPER AND PERCENT YIELD KEY
CHEMICAL REACTIONS OF COPPER AND PERCENT YIELD Objective To gain familiarity with basic laboratory procedures, some chemistry of a typical transition element, and the concept of percent yield. Apparatus
More informationEXPERIMENT 15: Ideal Gas Law: Molecular Weight of a Vapor
EXPERIMENT 15: Ideal Gas Law: Molecular Weight of a Vapor Purpose: In this experiment you will use the ideal gas law to calculate the molecular weight of a volatile liquid compound by measuring the mass,
More informationSyllabus CHM 2202 Organic Chemistry Laboratory II Spring 2011
Villanova University Department of Chemistry Syllabus CHM 2202 Organic Chemistry Laboratory II Spring 2011 Text: C.E. Bell, D.F. Taber and A.K. Clark, Organic Chemistry Laboratory with Qualitative Analysis,
More informationISOLATION OF CAFFEINE FROM TEA
ISLATIN F CAFFEINE FRM TEA Introduction In this experiment, caffeine is isolated from tealeaves. The chief problem with the isolation is that caffeine does not exist alone in the tealeaves, but other natural
More informationExperiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation
Experiment 8 Preparation of Cyclohexanone by ypochlorite xidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that
More informationSynthesis of tetraamminecopper(ii) sulfate, [Cu(NH 3 ) 4 ]SO 4 The reaction for making tetraamminecopper(ii) sulfate and some molar masses are:
Experiment 9 Synthesis of a opper oordination omplex and Aspirin with Demonstrations of the Synthesis of Nylon, Bakelite, and Polyvinyl Alcohol Slime Synthesis of tetraamminecopper(ii) sulfate, [u(n 3
More informationNeutralization Reactions. Evaluation copy
Neutralization Reactions Computer 6 If an acid is added to a base, a chemical reaction called neutralization occurs. An example is the reaction between nitric acid, HNO 3, and the base potassium hydroxide,
More informationPreparation of an Alum
Preparation of an Alum Pages 75 84 Pre-lab = pages 81 to 82, all questions No lab questions, a lab report is required by the start of the next lab What is an alum? They are white crystalline double sulfates
More informationPhysical Properties of a Pure Substance, Water
Physical Properties of a Pure Substance, Water The chemical and physical properties of a substance characterize it as a unique substance, and the determination of these properties can often allow one to
More informationElectrophilic Aromatic Substitution Reactions
Electrophilic Aromatic Substitution Reactions, Course Notes Archive, 1 Electrophilic Aromatic Substitution Reactions An organic reaction in which an electrophile substitutes a hydrogen atom in an aromatic
More informationAcid Base Titrations
Acid Base Titrations Introduction A common question chemists have to answer is how much of something is present in a sample or a product. If the product contains an acid or base, this question is usually
More informationSYNTHESIS AND ANALYSIS OF A COORDINATION COMPOUND OF COPPER
Chemistry 111 Lab: Synthesis of a Copper Complex Page H-1 SYNTHESIS AND ANALYSIS OF A COORDINATION COMPOUND OF COPPER In this experiment you will synthesize a compound by adding NH 3 to a concentrated
More informationRecovery of Elemental Copper from Copper (II) Nitrate
Recovery of Elemental Copper from Copper (II) Nitrate Objectives: Challenge: Students should be able to - recognize evidence(s) of a chemical change - convert word equations into formula equations - perform
More informationExperiment 8 - Double Displacement Reactions
Experiment 8 - Double Displacement Reactions A double displacement reaction involves two ionic compounds that are dissolved in water. In a double displacement reaction, it appears as though the ions are
More informationGreen Principles Atom Economy Solventless Reactions Catalysis
Lab 5: The Aldol Reaction Solventless vs Traditional Reactions: (Melting Point Study & Recrystallization) (adapted from Doxsee, K.M. and Hutchison, J.E., Green Organic Chemistry and John Thompson; Lane
More informationExperiment 2: Recrystallization & Melting Point
Experiment 2: Recrystallization & Melting Point Part A: Choosing a Solvent Part B: Purification of Phenacetin Reading: Mohrig, Hammond & Schatz Ch. 15 pgs 183-197 Ch. 10 pgs 104-113 Ch. 14 pgs 174-182
More informationThe Empirical Formula of a Compound
The Empirical Formula of a Compound Lab #5 Introduction A look at the mass relationships in chemistry reveals little order or sense. The ratio of the masses of the elements in a compound, while constant,
More informationPET Recycling. Nicholas Robusto Maggie Ifarraguerri Nathaniel Lawton Isabel Hefner
PET Recycling Nicholas Robusto Maggie Ifarraguerri Nathaniel Lawton Isabel Hefner OBJECTIVES Hydrolyze a sample of Polyethylene Terephthalate (PET) obtained from used soda bottles, and synthesize a dimer
More informationNeutralizing an Acid and a Base
Balancing Act Teacher Information Objectives In this activity, students neutralize a base with an acid. Students determine the point of neutralization of an acid mixed with a base while they: Recognize
More informationAN EXPERIMENT IN ALCHEMY: COPPER TO SILVER TO GOLD 2005, 2000, 1996 by David A. Katz. All rights reserved
AN EXPERIMENT IN ALCHEMY: COPPER TO SILVER TO GOLD 2005, 2000, 1996 by David A. Katz. All rights reserved INTRODUCTION One of the goals of the ancient alchemists was to convert base metals into gold. Although
More informationCHEMISTRY 338 THE SYNTHESIS OF LIDOCAINE
CHEMISTRY 338 THE SYTHESIS F LIDCAIE Lidocaine (1) is the common name of an important member of a category of drugs widely used as local anesthetics. Trade names for this substance include Xylocaine, Isocaine,
More informationExperiment #7: Esterification
Experiment #7: Esterification Pre-lab: 1. Choose an ester to synthesize. Determine which alcohol and which carboxylic acid you will need to synthesize your ester. Write out the reaction for your specific
More informationREACTIONS OF AROMATIC COMPOUNDS
A STUDENT SHOULD BE ABLE TO: REACTIONS OF AROMATIC COMPOUNDS 1. Predict the product(s) of Electrophilic Aromatic Substitution (EAS), Nucleophilic Aromatic Substitution (S N Ar) and Elimination-Addition
More informationElectrophilic Aromatic Substitution
Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution: a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring
More informationChemistry Notes for class 12 Chapter 13 Amines
1 P a g e Chemistry Notes for class 12 Chapter 13 Amines Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms ofnh 3 molecule by alkyl/aryl group(s).
More informationExperiment 3 Limiting Reactants
3-1 Experiment 3 Limiting Reactants Introduction: Most chemical reactions require two or more reactants. Typically, one of the reactants is used up before the other, at which time the reaction stops. The
More informationOrganic Lab 1 Make-up Experiment. Extraction of Caffeine from Beverages. Introduction
Organic Lab 1 Make-up Experiment Extraction of Caffeine from Beverages Introduction Few compounds consumed by Americans are surrounded by as much controversy as caffeine. One article tells us that caffeine
More informationGRIGNARD REACTION: PREPARATION OF TRIPHENYLMETHANOL (12/22/2009)
GRIGNARD REACTIN: PREPARATIN F TRIPHENYLMETHANL (12/22/2009) Grignard reagents are among the most versatile organometallic reagents, and they are the easiest organometallic reagent to prepare. Grignard
More informationAim To prepare a sample of cuprammonium rayon threads from filter paper.
Aim To prepare a sample of cuprammonium rayon threads from filter paper. Apparatus Required a) Conical flask (preferably 250 ml) b) Funnel c) Glass rod d) Beaker (preferably 250 ml) e) Water bath f) Filter
More informationCarolina s Solution Preparation Manual
84-1201 Carolina s Solution Preparation Manual Instructions Carolina Biological Supply Company has created this reference manual to enable you to prepare solutions. Although many types of solutions may
More informationReminder: These notes are meant to supplement, not replace, the textbook and lab manual. Electrophilic Aromatic Substitution notes
Reminder: These notes are meant to supplement, not replace, the textbook and lab manual. Electrophilic Aromatic Substitution notes History and Application: The rate of a reaction directly impacts the commercial
More informationCHEM 322: Azo Dyes: Combinatorial Synthesis of Dyes
CEM 322: Azo Dyes: Combinatorial Synthesis of Dyes Introduction: Compounds containing one or more azo groups (-=- linked to two carbon atoms) have a variety of uses. Aliphatic azo compounds, like azobisisobutyronitrile
More informationEXPERIMENT 12: Empirical Formula of a Compound
EXPERIMENT 12: Empirical Formula of a Compound INTRODUCTION Chemical formulas indicate the composition of compounds. A formula that gives only the simplest ratio of the relative number of atoms in a compound
More informationCHEM 211 CHAPTER 16 - Homework
CHEM 211 CHAPTER 16 - Homework SHORT ANSWER Consider the Friedel-Crafts alkylation reaction below to answer the following question(s): 1. Refer to the reaction above. Draw the structure of the electrophilic
More informationDetermining the Quantity of Iron in a Vitamin Tablet. Evaluation copy
Determining the Quantity of Iron in a Vitamin Tablet Computer 34 As biochemical research becomes more sophisticated, we are learning more about the role of metallic elements in the human body. For example,
More informationOrganic Chemistry Lab Experiment 4 Preparation and Properties of Soap
Organic Chemistry Lab Experiment 4 Preparation and Properties of Soap Introduction A soap is the sodium or potassium salt of a long-chain fatty acid. The fatty acid usually contains 12 to 18 carbon atoms.
More informationACID-BASE TITRATIONS: DETERMINATION OF CARBONATE BY TITRATION WITH HYDROCHLORIC ACID BACKGROUND
#3. Acid - Base Titrations 27 EXPERIMENT 3. ACID-BASE TITRATIONS: DETERMINATION OF CARBONATE BY TITRATION WITH HYDROCHLORIC ACID BACKGROUND Carbonate Equilibria In this experiment a solution of hydrochloric
More informationChem 1B Saddleback College Dr. White 1. Experiment 8 Titration Curve for a Monoprotic Acid
Chem 1B Saddleback College Dr. White 1 Experiment 8 Titration Curve for a Monoprotic Acid Objectives To learn the difference between titration curves involving a strong acid with a strong base and a weak
More informationDetermination of a Chemical Formula
1 Determination of a Chemical Formula Introduction Molar Ratios Elements combine in fixed ratios to form compounds. For example, consider the compound TiCl 4 (titanium chloride). Each molecule of TiCl
More informationThe Chemistry of Carbohydrates
The Chemistry of Carbohydrates Experiment #5 Objective: To determine the carbohydrate class of an unknown by carrying out a series of chemical reactions with the unknown and known compounds in each class
More informationMaking Biodiesel from Virgin Vegetable Oil: Teacher Manual
Making Biodiesel from Virgin Vegetable Oil: Teacher Manual Learning Goals: Students will understand how to produce biodiesel from virgin vegetable oil. Students will understand the effect of an exothermic
More informationCHEMICAL DETERMINATION OF EVERYDAY HOUSEHOLD CHEMICALS
CHEMICAL DETERMINATION OF EVERYDAY HOUSEHOLD CHEMICALS Purpose: It is important for chemists to be able to determine the composition of unknown chemicals. This can often be done by way of chemical tests.
More informationExtraction of Caffeine from Energy Drinks
Boston University OpenBU Chemistry http://open.bu.edu Organic Chemistry Laboratory Experiments 2011-07-14 Extraction of Caffeine from Energy Drinks Mulcahy, Seann P. http://hdl.handle.net/2144/1418 Boston
More informationPURIFICATION TECHNIQUES
DETERMINACIÓN DE ESTRUCTURAS ORGÁNICAS (ORGANIC SPECTROSCOPY) PURIFICATION TECHNIQUES Hermenegildo García Gómez Departamento de Química Instituto de Tecnología Química Universidad Politécnica de Valencia
More informationEXPERIMENT 7 Reaction Stoichiometry and Percent Yield
EXPERIMENT 7 Reaction Stoichiometry and Percent Yield INTRODUCTION Stoichiometry calculations are about calculating the amounts of substances that react and form in a chemical reaction. The word stoichiometry
More informationEXPERIMENT 10 Chemistry 110. Solutions Part 2 ACIDS, BASES, AND ELECTROLYTES
EXPERIMENT 10 Chemistry 110 Solutions Part 2 ACIDS, BASES, AND ELECTROLYTES PURPOSE: The purpose of this experiment is to determine the properties of solutions of acids, bases and electrolytes. Students
More informationEXPERIMENT 12 A SOLUBILITY PRODUCT CONSTANT
PURPOSE: 1. To determine experimentally the molar solubility of potassium acid tartrate in water and in a solution of potassium nitrate. 2. To examine the effect of a common ion on the solubility of slightly
More informationThe Analytical Balance
Chemistry 119: Experiment 1 The Analytical Balance Operation of the Single-Pan Analytical Balance Receive instruction from your teaching assistant concerning the proper operation of the Sartorius BP 210S
More informationTaking Apart the Pieces
Lab 4 Taking Apart the Pieces How does starting your morning out right relate to relief from a headache? I t is a lazy Saturday morning and you ve just awakened to your favorite cereal Morning Trails and
More informationQ.1 Draw out some suitable structures which fit the molecular formula C 6 H 6
Aromatic compounds GE 1 BENZENE Structure Primary analysis revealed benzene had an... empirical formula of and a molecular formula of 6 6 Q.1 Draw out some suitable structures which fit the molecular formula
More informationDetermination of Melting Points
Determination of Melting Points This experiment consists of three parts. In the first part, you will determine the melting point range of three known compounds. This part is mostly for practice, to make
More informationExperiment 6 Coffee-cup Calorimetry
6-1 Experiment 6 Coffee-cup Calorimetry Introduction: Chemical reactions involve the release or consumption of energy, usually in the form of heat. Heat is measured in the energy units, Joules (J), defined
More informationAcid-Base Extraction.
Acid-Base Extraction. Extraction involves dissolving a compound or compounds either (1) from a solid into a solvent or (2) from a solution into another solvent. A familiar example of the first case is
More informationCOMMON LABORATORY APPARATUS
COMMON LABORATORY APPARATUS Beakers are useful as a reaction container or to hold liquid or solid samples. They are also used to catch liquids from titrations and filtrates from filtering operations. Bunsen
More informationJuice Titration. Background. Acid/Base Titration
Juice Titration Background Acids in Juice Juice contains both citric and ascorbic acids. Citric acid is used as a natural preservative and provides a sour taste. Ascorbic acid is a water-soluble vitamin
More information