Chapter 5. Chemical Extraction
|
|
- Claude Ryan
- 6 years ago
- Views:
Transcription
1 Chapter 5. Chemical Extraction 1. Solid-liquid extraction 2. Liquid-liquid extraction 1 Introduction - Extraction is a physical process by which a compound is transferred from one phase to another : - Water soluble components in the tea leaves or in the coffee beans are transferred from a solid phase in the leaves or beans into a liquid phase the boiling water. This process is known as solid-liquid extraction. - Liquid-liquid extraction is a basic operation that should be measured in the organic chemistry laboratory : 2
2 Soxhlet Extraction - If a component in a solid mixture has a low solubility a Soxhlet extraction canbeused to isolate it. - The solid mixture is placed in a porous thimble which is repeatedly washed with fresh condensing solvent in a specialized piece of glassware know as Soxhlet extractor Condenser Syphon Tube Compound to be extracted Extraction Thimble Insoluble material Vapor By-pass Tube 3 Soxhlet Extraction
3 Soxhlet Extraction - The condensing solvent falls into the chamber in which the thimble is placed - Eventually the chamber fills and the liquid siphons back into the boiling flask - The process is repeated and the solid is eventually extracted into the boiling flask ilp.net/labtechniques/soxhletextractionvideo.htm Compound to be extracted Insoluble material 5 Chapter 5. Chemical Extraction 1. Solid-liquid extraction 2. Liquid-liquid extraction 6
4 Introduction - Liquid-liquid extraction is a basic operation that should be measured in the organic chemistry laboratory : - By liquid-liquid extraction we can isolate single components from a mixture. The physical process that rules liquid-liquid extraction is known as solvent-solvent partitioning or the distribution of solutes between pair of solvents(immiscible solvent). 7 Introduction - Solvents such as diethyl ether, tertbutyl methyl ether, methylene chloride and toluene have very limited solubility in water. The solubility of water in such solvents is also very low. We say that these solvents are immiscible with water. - Two layer system is obtained : (lower layer) dense solvent (upper layer) less dense solvent Toluene (d=0.867) Water (d=1.000) - The organic solvent layer is called the organic layer or organic phase and the water layer the aqueous layer or aqueous phase. - Inorganic and water soluble materials will stay in the aqueous(water) layer and more organic molecules will remain in the organic layer 8
5 Immiscibility & Density of sovlent - The densities of the solvents will predict which solvent is the top or bottom layer. - In general, the density of nonhalogenated organic solvents are less than 1.0 g/ml and halogenated solvents are greater than 1.0 g/ml. - One common solvent pair is dichloromethane and water(aqueous layer). Common extraction solvents listed by density. (ex. diethyl ether, methyl tert butyl ether) (=Methylene chloride) (=trichloromethane) 9 Solvent-Solvent Partitioning Immiscible Miscible 10
6 Solvent-Solvent Partitioning d=1.000g/ml d=1.492g/ml Organic phase Aqueous phase Solvent Nonpolar solvent Water Solute Nonpolar solutes dissolve here Ionic and polar solutes dissolve here Density The organic phase does not always float on top. Chloroform, for example, sinks below the aqueous phase. Water is usually denser than other solvents, but some organic solvents are even denser. 11 Solvent-Solvent Partitioning - Lets recall the golden rule of solubility: like dissolves like; Highly polar and ionic compounds are readily soluble in water but have very low solubility in most organic solvents, which are polar than water. - On the other hand organic compounds of medium and low polarity are more soluble in organic solvents than water. - This selective solubility behavior can be advantageously used to separate compounds by liquid-liquid extraction. 12
7 Solvent-Solvent Partitioning - ex1. Due to their high solubility in water and low solubility in organic solvents, very polar solutes such as ionic compounds and sugars, display very low partition coefficients between most organic solvents and water. Therefore these solutes remain in the water phase even after several extractions with organic solvents. - ex2. Conversely organic compounds of medium and low polarity for example, cholesterol, DDT(Dichloro Diphenyl Trichloroethane), and aspirin have larger partition coefficients and thus are easily extracted into organic solvents. 13 Criteria for selecting an extracting solvent The organic solvent used for extraction must meet a few criteria: - Should readily dissolve substance to be extracted. - Should not react with the substance to be extracted. - Should not react with or be miscible with water (the usual second solvent). - Should have a low boiling point so it can be easily removed from the product. - Should be reasonably safe to work with and relatively inexpensive. Common extraction solvents are diethyl ether and methylene chloride. 14
8 Criteria for selecting an extracting solvent 15 Nernst Distribution Law - In the simplest extraction case, the distribution ratio is constant in accordance with the classical Nernst distribution law; Nobel Prize in Chemistry At constant temperature, a solute distributes itself between two immiscible solvents only in a particular ratio. 16
9 Distribution Ratio (Partition Coefficient) - Lets suppose that we add a solute A to a mixture of water and toluene, shake the system thoroughly to attain equilibrium, and allow it to settle. - Solute A will be present in both layers but we expect to find it in a larger amount in the solvents is directed by the Distribution coefficients of A between the solvents. - The Distribution ratio is the ratio of the total analytical concentration of a solute in the extract (regardless of its chemical form) to its total analytical concentration in the other phase The phrase Partition coefficient" is now considered obsolete by IUPAC, and Distribution ratio" is more appropriate terms that should be used 17 Distribution Ratio - The distribution of a solute between two immiscible solvents can be described by the Distribution Ratio D. D = [solute] 1 [solute] 2 where, [solute] represents the stoichiometric or formal concentration of a solute and the subscripts 1 and 2 refer to the two phases. - Since in most cases, two-phase system is of analytical interest, an organic(org) solvent and aqueous(aq) are involved, D will be understood to be; - ex. D = [solute] Org [solute] Aq D Toluene/Water = [A Toluene ] / [A Water ], 18
10 Distribution Ratio - If the ionized species has an appreciable solubility only in the aqueous phase, then the distribution coefficient, D, can be defined as D = [solute u ] Org [solute u ] Aq + [solute i ] Aq where, [solute] Org : the conc. of the unionized species in organic phase [solute] Aq : the conc. of the unionized species in aqueous phase [solute] Aq : the conc. of the ionized species in aqueous phase 19 % Extraction - The more commonly used term for expressing the extraction efficiency by analytical chemist is the percent extraction E, which is related to D as where V represent solvent volume - The percent extraction may be seen to vary with the volume ratio of the two phases as well as with D. - At extreme values of D, E becomes less sensitive to changes in D. For example, at a phase volume ratio of unity(v aq =V org ), for D values from 500 to 1000, the value of E changes only from 99.5 to 99.9%. 20
11 Extraction procedure The total capacity of the separatory funnel should be at least twice the volume of the solution - Stopper the funnel and invert it. Slowly open the stopcock to release any built up pressure, then close the stopcock. - Gently shake the separatory funnel to allow intimate mixing of the solutions (Caution: When shaken, the mixture may develop pressure; be sure to vent it periodically). - Clamp the separatory funnel to a retort stand and allow the mixture to separate into two layers. - Remove the stopper and collect the layer containing the compound what we want to obtain. Vacuum rotary evaporation 21 Extraction Techniques: Layer identification - One of the most common and frustrating mistakes made by beginners to liquid-liquid extraction is to keep the wrong phase and discard the one with the desired product. - In principle the identity of the layers can be predicted by the density of the solvents. - However a high solute concentration may change the density of the solution to the point that the layer with the less-dense solvent becomes the denser and lower layer. ex. Saturated sodium chloride solution : 1.2 g/ml Conc. Sulfuric acid : 1.8g/ml 22
12 Extraction Techniques: Layer identification - If there is any doubt concerning the identity of the layers the following test should be performed: Place about 1 ml of water in a test tube and add a few drops of the upper layer with a Pasteur pipet. If the drops dissolve in the water, it means they come from the aqueous phase. If the drops are immiscible with the water in the test tube, they belong to the organic phase. 23 Extraction Techniques: Multiple extraction - Since the distribution coefficient is a ratio, unless K is very large, not all of a solute will reside in the organic layer in a single extraction. - Usually two, three, or four extractions of the aqueous layer with an organic solvent are carried out in sequence in order to remove as much of the desired product from the aqueous layer as possible. - The effectiveness of multiple small volume extractions : if one extraction can recover 90% of the compound. A second extraction with the same solvent may be able to pull out 90% of the remaining material. Effectively 99% of the compound was recovered with two extractions. - Many smaller extractions are more efficient than one large extraction. This phenomenon can be proved mathematically, but in short follows the equation: 24
13 Extraction Techniques: Multiple extraction - Many smaller extractions are more efficient than one large extraction : Fraction of material extracted by solvent B is where, n : the number of extractions performed, K : the distribution coefficient, V A, V B : the volume of solvent A and B 25 Extraction Techniques: Multiple extraction Example Prob. Give at 20 o C only 0.24 g of an organic acid A dissolves in 100 ml of water, but 2.70 g of the same acid dissolves in 100 ml of ether. a) calculate the value of partition coefficient. : b) calculate the percentage of extraction if 0.12 g of acid extracted in 100 ml of aqueous solution: 92 % c) calculate the volume of ether required to extract 85% of a 3.00 g of acid A in 100 ml solution : 51 ml d) calculate the total amount of acid extracted by a double extraction of 50 ml ether in each extraction in part ( c). First extraction (first 50 ml ether) : X o1 = 2.57 g acid extracted in first extraction X w1 = 3.00 g 2.57 g = 0.43g acid remained in aqueous solution after first extraction Second extraction (second 50 ml ether) X o2 = 0.38 g acid extracted in first extraction X o (total) = X o1 + X o2 = 2.57 g g = 2.93 g %E = (2.93 /3.00) x100 = 97.7 % 26
14 Breaking Emulsions - After shaking the two phases may fail to separate sharply and may instead form a suspension of one liquid in the other. This is called emulsion and it is unwelcome in the laboratory. - In order to break the emulsion and get a clean separation between layers, Swirl the funnel very gently. If the emulsion persists add a small amount of a saturated solution of sodium chloride in water: The sodium chloride increases the ionic strength of the water phase and decreases its miscibility with the organic solvent. This process is called salting out and may help break the emulsion. - Swirl the flask occasionally over a period of 5-10 minutes and then gravity-filter the system using flutted filter paper. Rinse the magnesium sulfate on the filter with a few milliliters of the same organic solvent. Discard the magnesium sulfate. The solution should be clear now. - Another way of breaking the emulsions is to centrifuge the layers for a few minutes. Glass tubes are preffered for this operation because some organic solvents may dissolve plastic centrifuge tubes. 27 Microscale Liquid liquid Extraction - When small volumes ( ml) are to be extracted, a conical vial or a screw capped test tube are the glass ware of choice. Conical vials are available in different sizes (0.5-5mL), test tubes are suitable when the volume to be extracted is between 2 and 10 ml. - The solution of the desired compound and the extracting solvent are placed in the vial, the total volume should not be larger than three-fourths of the maximum capacity of the vial. - The vial is tightly capped and shaken vigorously for a few seconds. The pressure is released by carefully unscrewing the cap. This process is repeated four to six times. - The lower layer is withdrawn with the aid of a Pasteur pipet and placed in a clean test tube. In doing this operation squeeze the rubber bulb before immersing the Pasteur pipet in the extraction vial. This will prevent air bubbles from disrupting the interface between the phases. - Very volatile solvents such as diethyl ether and methylene chloride have a tendency to squirt out the tip of the pipet. One way is to saturate the inside of the pipet with the solvents vapors by drawing fresh solvent 28
15 Drying the Organic Layer - One significant problem with liquid/liquid extraction is that no solvent is COMPLETELY insoluble in another solvent. - After contact with an aqueous phase any organic solvent will be saturated with water, and this poses a problem in the recovery of the solute from the organic layer: evaporation of the solvent renders a product mixed with water. - Also, many reactions themselves are performed in an aqueous solution. This water must be removed before the required compound can be properly characterized. - To avoid these wet residues water should be removed before evaporation. Two methods of drying solutions are commonly used: saturated aqueous sodium chloride and solid drying agents. 29 Drying the Organic Layer: Saturated aqueous sodium chloride - The bulk of the water can often be removed by shaking or "washing" the organic layer with saturated aqueous sodium chloride (otherwise known as brine). - The salt water works to pull the water from the organic layer to the water layer: the concentrated salt solution wants to become more dilute and salts have a stronger attraction to water than to organic solvents. 30
16 Drying the Organic Layer Saturated aqueous sodium chloride - To dry your organic product by this method, place the organic solution (methylene chloride, d=1.3) in a separatory funnel. - Add an amount of saturated aqueous sodium chloride(d=1.2 g/ml), less than or equal to the amount of organic solution you have. - Stopper the funnel and shake as in an extraction. Allow the layers to separate. - Drain off the lower layer: in this case, this is the organic layer and the layer you want to save. Dispose of the aqueous layer in the aqueous waste carboy. 31 Solid drying agents Drying the Organic Layer - Final traces of water are removed by treating the organic solution with a drying agent. A drying agent is an inorganic salt which readily takes up water to become hydrated: drying over anhydrous sodium sulfate or other drying agent. - chemists remove the water from the organic layer by adding an insoluble inorganic solid to the solution which will absorb the water, thus drying it. - Granular anhydrous sodium sulfate is the drying agent most often used: all of the inorganic solids work by reacting with the water to form hydrates, if water is available. ethyl acetate was dried with a little Na 2 SO 4 (the solid at the bottom). Calcium chloride Magnesium sulfate Sodium sulfate 32
17 Drying the Organic Layer Solid drying agents Because these compounds will deliquesce (absorb moisture from the air), you MUST cap bottles of drying agents between uses! Otherwise, they will end up looking like this! Hydrated complexes for some common drying agents. 33 Drying the Organic Layer Solid drying agents - Add a small amount (but enough to ensure that all the water is removed) of the solid drying agent directly to the organic solution. - Swirl the solution and Observe the drying agent; if it is all clumped together, add more. - The pictures below show how a solution with drying agent looks when it is clumped and when it is free-flowing. - In most cases, drying is as complete as it will get in 20 minutes. When drying is complete, you need to remove the dried organic solution from the drying agent. 34
18 Drying the Organic Layer Solid drying agents - If the powder is quite fine (as when using magnesium sulfate) or if the volume is large, gravity filtration is the method of choice. - If the drying agent is of larger particle size (as when using sodium sulfate or calcium chloride), decanting is the method of choice. - An alternative to decanting is removing the liquid from the drying agent simply by drawing it off with a Pasteur pipet. decanting 35 Drying the Organic Layer Solid drying agents - There are other choices for drying agents including molecular sieves and sodium metal. There are benefits and disadvantages to each one. Sodium: A very powerful drying agent, removes traces of water from solvents such as toluene, benzene and diethyl ether and aliphatic amines before distillation. It reacts violently with water. It should be handled with extreme care by trained people only. Molecular sieves: Small spheres made of porous aluminosilicates. The average pore size is 3 and 4Å respectively. 36
Extraction. weak base pk a = 4.63 (of ammonium ion) weak acid pk a = 4.8. weaker acid pk a = 9.9. not acidic or basic pk a = 43
Extraction Background Extraction is a technique that separates compounds (usually solids) based on solubility. Depending on the phases involved, extractions are either liquid-solid or liquid-liquid. If
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 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 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 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 informationThe ratio of the concentrations of a substance in the two solvents at equilibrium is called its distribution coefficient, K D :
CHM 147 Advanced Chemistry II Lab Extraction: A Separation and Isolation Technique Adapted from Extraction: A Separation and isolation Technique, Hart, Harold; Craine, Leslie; Hart, David; Organic Chemistry,
More informationEXTRACTION: A SEPARATION AND PURIFICATION TECHNIQUE
E6-1 Experiment 6 Fig. 6-1 EXTRATIN: A SEPARATIN AND PURIFIATIN TENIQUE (with a possibly unexpected result) New Techniques Discussion R carboxylic acid + Na + 2 R _ Na + sodium carboxylate ippocrates (460-377
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 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 informationSpring Renan Gongora Week Two: Extraction
Spring 2017 Renan Gongora Week Two: Extraction Disclaimer The information provided here is to help facilitate learning and a smoother in-lab experience but you need to read all procedures!!! Furthermore,
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 informationExperiment DE: Part II Fisher Esterification and Identification of an Unknown Alcohol
Experiment DE: Part II Fisher Esterification and Identification of an Unknown Alcohol Fisher Esterification of an Alcohol (Fraction A) On the Chem 113A website, under "Techniques" and "Videos" review the
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 informationIntroduction To A General Organic Work-Up. Na HCl. O Phenylalanine Water-Soluble Anion Organo-Soluble
Introduction To A General rganic Work-Up ften times the most difficult part of conducting an experiment is the work-up that follows. In this exercise you will be introduced to the fundamental techniques
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 informationExperiment 1: Extraction and Thin Layer Chromatography
Experiment 1: Extraction and Thin Layer Chromatography Introduction: Chromatography is a useful tool in chemistry and can be very helpful in determining the composition of an unknown sample. In chromatography
More informationMethods of Separation. Vacuum Filtration. Distillation. The Physical Separation of Matter Chemistry 11 2/17/2014
The Physical Separation of Matter Chemistry 11 Methods of Separation n Depending upon the physical properties of the substances involved, various methods of separation can be used. n Hand separation: A
More informationExtraction. A useful technique for purification of mixture. Dr. Zerong Wang at UHCL. Separation processes
Extraction A useful technique for purification of mixture Separation processes Liquid-liquid extraction Adsorption Filtration Solid-liquid extraction (leaching) Elution chromatography Membrane separation
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 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 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 informationPrelab Reading Assignment: Laboratory Techniques in Organic Chemistry, 4 th Ed. Chapter 19
CHEM 213 Technique Experiments Experiment 5: Column Chromatography Number of labs - one Reactions performed None Chemicals used: Fluorene-fluorenone mixture, hexanes, methylene chloride, silica gel Supplies
More informationChromatography Extraction and purification of Chlorophyll CHM 220
INTRODUCTION Extraction and purification of naturally occurring molecules is of the most common methods of obtaining organic molecules. Locating and identifying molecules found in flora and fauna can provide
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 informationMethods of purification
Methods of purification Question Paper 1 Level IGSE Subject hemistry (0620/0971) Exam oard ambridge International Examinations (IE) Topic Experimental techniques Sub-Topic Methods of purification ooklet
More informationAcid-Base Extraction. 1
Acid-Base Extraction. 1 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 informationThe Fragrance of Rum, Isobutyl Propionate
The Fragrance of Rum, Isobutyl Propionate Exp t 82 from K. L. Williamson, Macroscale and Microscale rganic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston p385; revised Prelab Exercise 6/27/06 Give
More informationExtraction. W. H. Bunnelle, L. A. Meyer, R. E. Glaser (Version 4) Introduction
Extraction W. H. Bunnelle, L. A. Meyer, R. E. Glaser (Version 4) Introduction Chances are, everyone in this class has done an extraction, probably several of them. Ever make a cup of tea or a pot of coffee?
More informationExperiment 9 Dehydration of Methylcyclohexanol Friday/Monday 1
Experiment 9 Dehydration of Methylcyclohexanol Friday/Monday 1 There are three distinct steps in most organic preparative reactions: 1) the reaction itself, 2) isolation of the crude product, and 3) final
More informationWater and Aqueous Systems
Water and Aqueous Systems The Water Molecule: a Review Water is a simple tri-atomic molecule, H 2 O Each O-H bond is highly polar, because of the high electronegativity of the oxygen (N, O, F, and Cl have
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 informationChemistry 151 Last Updated Dec Lab 8: Precipitation Reactions and Limiting Reagents
Chemistry 151 Last Updated Dec. 2013 Lab 8: Precipitation Reactions and Limiting Reagents Introduction In this lab you will perform a simple precipitation reaction between strontium nitrate and potassium
More informationExperiment 1: The Borohydride Reduction of 9-Fluorenone to 9-Fluorenol
Experiment 1: The Borohydride Reduction of 9-Fluorenone to 9-Fluorenol Background: In this week s experiment, a metal hydride will be used as a reducing agent. Metal hydrides can be quite reactive, and
More informationExperiment 1 SOLUBILITY. TIME ESTIMATE: Parts A-D (3 hours); Part E (1 hour); Part F (1 hour) CHEMICALS AND SUPPLIES PER 10 STUDENTS:
Experiment 1 SOLUBILITY TIME ESTIMATE: Parts A-D (3 hours); Part E (1 hour); Part F (1 hour) CHEMICALS AND SUPPLIES PER 10 STUDENTS: Part A Benzophenone (Grind up the flakes into a powder) Malonic acid
More information4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester
NP 4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NaEt C 10 H 18 4 Na C 2 H 6 C 8 H 12 3 (202.2) (23.0) (46.1) (156.2) Classification Reaction types and substance
More informationMETHOD 3510B SEPARATORY FUNNEL LIQUID-LIQUID EXTRACTION
METHOD 3510B SEPARATORY FUNNEL LIQUID-LIQUID EXTRACTION 1.0 SCOPE AND APPLICATION 1.1 This method describes a procedure for isolating organic compounds from aqueous samples. The method also describes concentration
More informationEXPERIMENT 22 SOLUBILITY OF A SLIGHTLY SOLUBLE ELECTROLYTE
EXPERIMENT 22 SOLUBILITY OF A SLIGHTLY SOLUBLE ELECTROLYTE INTRODUCTION Electrolytes are compounds that are present in solution as ions. They are more likely to be soluble in water than in most other liquids
More informationORGANIC SYNTHESIS: MICROWAVE-ASSISTED FISCHER ESTERIFICATION
EXPERIMENT 7 ORGANIC SYNTHESIS: MICROWAVE-ASSISTED FISCHER ESTERIFICATION Materials Needed 1.0-2.0 ml of an alcohol to be chosen from the following: 3-methyl 1-butanol (isoamyl alcohol, isopentyl alcohol),
More informationPart II. Cu(OH)2(s) CuO(s)
The Copper Cycle Introduction In this experiment, you will carry out a series of reactions starting with copper metal. This will give you practice handling chemical reagents and making observations. It
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 information2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide
217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of
More informationExperiment 2 - Using Physical Properties to Identify an Unknown Liquid
Experiment 2 - Using Physical Properties to Identify an Unknown Liquid We usually think of chemists as scientists who do things with chemicals. We can picture a chemist's laboratory with rows of bottles
More informationIntroductory Remarks:
Introductory Remarks: At all times while you are in the laboratory you should wear safety spectacles or own spectacles if they have been approved. Eating of any kind of food or drinking is strictly prohibited
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 informationDETERMINATION OF THE SOLUBILITY PRODUCT OF GROUPII HYDROXIDES
INTRODUCTION DETERMINATION OF THE SOLUBILITY PRODUCT OF GROUPII HYDROXIDES SOLUBILTY EQUILIBRIA Many systems in chemistry appear to be static when in fact they are in (dynamic) equilibrium. When a system
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 informationPHYSICAL CONSTANTS: MELTING POINTS, BOILING POINTS, DENSITY
CRYSTALLIZATION: PURIFICATION OF SOLIDS ANSWERS TO PROBLEMS: 1. (a) (b) (c) (d) A plot similar to line A in Figure 5.1 on page 559 will be obtained. The line will be slightly curved. All of the substance
More informationLab 6 Guide: Extraction (Sept 29 Oct 5)
Lab 6 Guide: Extraction (Sept 29 Oct 5) Extraction and Determination of a Distribution Coefficient, Exp. 4A, pages 33-46 in Taber The purpose of this lab is to calculate the K d of benzoic acid in dichloromethane.
More informationExperiment 20-Acid-Base Titration: Standardization of KOH and Determination of the Molarity and/or Percent Composition of an Acid Solution
Experiment 20-Acid-Base Titration: Standardization of KOH and Determination of the Molarity and/or Percent Composition of an Acid Solution In this experiment, you will determine the molarity and percent
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 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 informationThin Layer Chromatography
Thin Layer Chromatography Thin-layer chromatography involves the same principles as column chromatography, it also is a form of solid-liquid adsorption chromatography. In this case, however, the solid
More informationUniversal Indicator turns green. Which method is used to obtain pure solid X from an aqueous solution? A. mixture
1 The results of some tests on a colourless liquid X are shown. oiling point = 102 Universal Indicator turns green What is X? ethanol hydrochloric acid pure water sodium chloride (salt) solution 2 blue
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 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 informationMETHOD 3520C CONTINUOUS LIQUID-LIQUID EXTRACTION
METHOD 3520C CONTINUOUS LIQUID-LIQUID EXTRACTION 1.0 SCOPE AND APPLICATION 1.1 This method describes a procedure for isolating organic compounds from aqueous samples. The method also describes concentration
More informationNaBr, H2SO4 CH3CH2CH2CH2Br + NaHSO4 + H2O. 1-Bromobutane bp C den MW n 1.439
Exp t 140 The SN2 Reaction: 1-Bromobutane from K. L. Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston. p247; revised 2/22/02 Prelab Exercise: Review the
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 informationCHEM 334 Quantitative Analysis Laboratory
Calibration of Volumetric Glassware Introduction Volumetric glassware is a class of glass vessels that are calibrated to contain or deliver certain volumes of substances. Graduated cylinders, pipettes
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 18 - Absorption Spectroscopy and Beer s Law: Analysis of Cu 2+
Experiment 18 - Absorption Spectroscopy and Beer s Law: Analysis of Cu 2+ Many substances absorb light. When light is absorbed, electrons in the ground state are excited to higher energy levels. Colored
More informationLACTIC ACID. The method is applicable to the determination of lactic acid and lactate salts (Note 2) in light or heavy steepwater.
LACTI.01-1 LACTIC ACID PRINCIPLE SCOPE Lactic acid in steepwater (Note 1) is oxidized to acetaldehyde following treatment with copper sulfate and calcium hydroxide to remove interfering substances. Acetaldehyde
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 informationVolumetric analysis involving acids and alkalis
Chapter 19 Volumetric analysis involving acids and alkalis 19.1 Standard solutions 19.2 Acid-alkali titrations 19.3 Calculations on volumetric analysis 19.4 Writing a laboratory report on volumetric analysis
More informationExp t 83 Synthesis of Benzyl Acetate from Acetic Anhydride
Exp t 83 Synthesis of Benzyl Acetate from Acetic Anhydride from K. L. Williamson, Macroscale and Microscale rganic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston p385; revised Prelab Exercise: 10/14/00
More informationLaboratory 1 CSI Meadville: Preparative purification of a mixture
CHEM 231: rganic Form and Function Laboratory 1 CSI Meadville: Preparative purification of a mixture Specific Practical Goals to effect physical separation by leveraging chemical properties to master the
More informationExperiment 14 - Qualitative Analysis
Introduction Qualitative analysis involves the identification of the substances in a mixture. When chemical methods are used in the identification of mixtures of metal cations, these ions are usually separated
More informationACID-BASE EXTRACTION
ACID-BASE EXTRACTION An acid-base extraction is a type of liquid-liquid extraction. It typically involves different solubility levels in water and an organic solvent. The organic solvent may be any carbon-based
More informationExtraction: Separation of Acidic Substances Notes
Reminder: These notes are meant to supplement, not replace, the laboratory manual. Extraction: Separation of Acidic Substances Notes Application: Acids and Bases are one the most fundamental principles
More informationUnit 11: Chapters 15 and 16
Unit 11: Chapters 15 and 16 Water and Solution Chemistry What makes Water Special? Extensive Hydrogen Bonding!! Unusually... high surface tension low vapor pressure high specific heat capacity high molar
More informationSEPARATION TECHNIQUES
SEPARATION TECHNIQUES If a substance does not dissolve in a solvent, we say that it is insoluble. For example, sand does not dissolve in water it is insoluble. Filtration is a method for separating an
More informationAcid / Base Titrations
Acid / Base Titrations v051413_7pm Objectives: Determine the concentration of a base solution using an acid standard. Optional: Precipitate an ionic salt for percent yield determination using the standardized
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 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 informationExperimental Procedure. Lab 406
Experimental Procedure Lab 406 Overview This experiment is to be complete in cooperation with other chemists/chemist groups in the laboratory. In PART A, a standardized solution of hydrochloric acid is
More information3. Separation of a Mixture into Pure Substances
3. Separation of a Mixture into Pure Substances Paper Chromatography of Metal Cations What you will accomplish in this experiment This third experiment provides opportunities for you to learn and practice:
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 informationLAB #6 Chromatography Techniques
LAB #6 Chromatography Techniques Objectives: To learn how to story board a procedure Explain how a chromatograph of pigments is formed from both paper and thin layer chromatography. Isolate and identify
More informationSupernatant: The liquid layer lying above the solid layer after a precipitation reaction occurs.
Limiting Reagent Introduction The quantities of substances involved in a chemical reaction represented by a balanced equation are often referred to as stoichiometric amounts. Solution stoichiometry is
More informationSupernatant: The liquid layer lying above the solid layer after a precipitation reaction occurs.
Limiting Reagent Introduction The quantities of substances involved in a chemical reaction represented by a balanced equation are often referred to as stoichiometric amounts. Solution stoichiometry is
More informationEster Synthesis And Analysis: Aspirin and Oil of Wintergreen. Vanessa Jones November 19, 2015 Thursday 8:30 Lab Section Lab Partner: Melissa Blanco
Ester Synthesis And Analysis: Aspirin and Oil of Wintergreen Vanessa Jones November 19, 2015 Thursday 8:30 Lab Section Lab Partner: Melissa Blanco INTRODUCTION For this lab, students attempted to synthesize
More informationTitrimetric Determination of EASTMAN Color Developing Agent, CD-3, in Process ECN-2 Developer with Sulfato Cerate
Titrimetric Determination of EASTMAN Color Developing Agent, CD-3, in Process ECN-2 Developer Sulfato Cerate ECN-0003/1 Process ECN-2 ECP-2B VNF-1/LC RVNP Formulas SD-49 INTRODUCTION This method describes
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 informationCHAPTER CHROMATOGRAPHIC METHODS OF SEPARATIONS
Islamic University in Madinah Department of Chemistry CHAPTER - ----- CHROMATOGRAPHIC METHODS OF SEPARATIONS Prepared By Dr. Khalid Ahmad Shadid Chemistry Department Islamic University in Madinah TRADITIONAL
More informationTHE CATHOLIC UNIVERSITY OF EASTERN AFRICA A. M. E. C. E. A
THE CATHOLIC UNIVERSITY OF EASTERN AFRICA A. M. E. C. E. A MAIN EXAMINATION P.O. Box 62157 00200 Nairobi - KENYA Telephone: 891601-6 Fax: 254-20-891084 E-mail:academics@cuea.edu JANUARY APRIL 2014 TRIMESTER
More informationHeat Capacity of Water A) heat capacity amount of heat required to change a substance s temperature by exactly 1 C
CHEMISTRY Ch. 13 Notes: Water and Its Solutions NOTE: Vocabulary terms are in boldface and underlined. Supporting details are in italics. 13.1 Notes I. Water Molecule Characteristics POLAR molecule (a
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 informationHYSICAL AND CHEMICAL PROPERTIES AND PHYSIC AND CHEMICAL CHANGES
Experiment 4 Name: 15 P HYSICAL AND CHEMICAL PROPERTIES AND PHYSIC AND CHEMICAL CHANGES 13 Al e In this experiment, you will also observe physical and chemical properties and physical and chemical changes.
More information2 nd exam of the 1 st term for 2 nd ESO G. 1. Look at the following picture:
2 nd exam of the 1 st term for 2 nd ESO G Name: 1. Look at the following picture: Date: What is the name of the separation technique that you see? What type of substances you separate with this technique?
More informationSolvothermal Technique Guidelines
Solvothermal Technique Guidelines When performing a solvothermal reaction, the first thing you need to do is to check the physical properties of your reactants. For a regular solvothermal reaction, there
More informationTITRATION OF AN ACID WITH A BASE
TITRATION OF AN ACID WITH A BASE 1 NOTE: You are required to view the podcast entitled Use of Burets for Titrations before coming to lab this week. To view the podcast, consisting of eight episodes, go
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 informationOxidation of Alcohols: Oxidation of Borneol to Camphor
Experiment 13 Oxidation of Alcohols: Oxidation of Borneol to Camphor Reading: Handbook for Organic Chemistry Lab, sections on Extraction (Chapter 8), Drying Organic Solutions (Chapter 11), and Solvent
More informationLab 3: Solubility of Organic Compounds
Lab 3: Solubility of rganic Compounds bjectives: - Understanding the relative solubility of organic compounds in various solvents. - Exploration of the effect of polar groups on a nonpolar hydrocarbon
More informationThe Characteristics of a Soln
Goal 1 The Characteristics of a Soln Define the term solution, and, given a description of a substance, determine if it is a solution. The Characteristics of a Soln Solution (as used in chemistry) A homogenous
More informationSection B: Some Essential Background Chemistry
Section B: Some Essential Background Chemistry Soluble and insoluble salts The importance of knowing whether a salt is soluble or insoluble in water You will remember that acids react with carbonates to
More informationEXPERIMENT #4 Separation of a Three-Component Mixture
OBJECTIVES: EXPERIMENT #4 Separation of a Three-Component Mixture Define chemical and physical properties, mixture, solubility, filtration, sublimation, and percent Separate a mixture of sodium chloride
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 informationBoiling Point ( C) Boiling Point ( F)
Technical Data of Cannabinoids Solvents Chemical Formula FW (g/mol) Boiling Point ( C) Boiling Point ( F) Melting Point ( C) Density (g/ml) Solubility in Water (g/100 g) Flash Point ( C) Isopropyl alcohol
More informationExperiment 20: Analysis of Vinegar. Materials:
Experiment 20: Analysis of Vinegar Materials: graduated cylinder 6 M NaOH: Dilute Sodium Hydroxide 1000 ml Florence Flask & stopper KHC 8 H 4 O 4 : Potassium Hydrogen Phthalate (KHP) 125 ml Erlenmeyer
More information