Exp t 83 Synthesis of Benzyl Acetate from Acetic Anhydride

Size: px
Start display at page:

Download "Exp t 83 Synthesis of Benzyl Acetate from Acetic Anhydride"

Transcription

1 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 Give the detailed mechanism for the synthesis of isobutyl formate by Fischer esterification. Introduction: The ester group is an important functional group that can be synthesized in a number of different ways. The low-molecular-weight esters have very pleasant odors and indeed are the major components of the flavor and odor aspects of a number of fruits. Although the natural flavor may contain nearly a hundred different compounds, single esters approximate the natural odors and are often used in the food industry for artificial flavors and fragrances. Esters can be prepared by the reaction of a carboxylic acid with an alcohol in the presence of a catalyst such as concentrated sulfuric acid, hydrogen chloride, p-toluenesulfonic acid, or the acid form of an ion exchange resin:

2 H 3 H H H H 3 H 2 This Fischer esterification reaction reaches equilibrium after a few hours of refluxing. The position of the equilibrium can be shifted by adding more of the acid or of the alcohol, depending on cost or availability. The mechanism of the reaction involves initial protonation of the carboxyl group, attack by the nucleophilic hydroxyl, a proton transfer, and loss of water followed by loss of the catalyzing proton to give the ester. Because each of these steps is completely reversible, this process is also, in reverse, the mechanism for the hydrolysis of an ester: ther methods are available for the synthesis of esters, most of them more expensive but readily carried out on a small scale. For example alcohols react with acid anhydrides to form esters and this is the method used in this experiment: H 3 H 3 H 2 H3H2H H3H Ethanol Acetic anhydride Ethyl acetate Acetic acid Acid chlorides form esters by reaction with alcohols. H 3 H 2 H 2 H H 3 l H 3 H 2H 2 Hl 1-Propanol Acetyl chloride n-propyl acetate In the latter reaction, an organic base such as pyridine is usually added to react with the hydrogen chloride. A number of other methods can be used to synthesize the ester group. Among these are the addition of 2-methylpropene to an acid to form t-butyl esters, the addition of ketene to make H 2 Ketene H 2 H Propionic Acid H 2 2-Methylpropene (isobutylene) HH 2 Benzyl alcohol H H 2 t-butyl propionate H 2 Benzyl Acetate H Ag 3 - Silver acetate BrH 2 H 2 H 1-Bromo-3-methylbutane H 2 H 2 H Isoamyl acetate

3 acetates, and the reaction of a silver salt with an alkyl halide. As noted above, Fischer esterification is an equilibrium process. onsider the reaction of acetic acid with 1-butanol to give n-butyl acetate: H 3 H Acetic acid HH 2 H 2 H 2 n-butanol The equilibrium expression for this reaction is shown below. Keq= H 3 H 3 H H H 2H 2 H 2 H 2 H 2 H 2 H 3 n-butylacetate [H2] [HH2H2H2H3] H2 For primary alcohols reacting with unhindered carboxylic acids, K eq ~4. If equal quantities of 1- butanol and acetic acid are allowed to react, the theoretical yield of ester is only 67% at equilibrium. To upset the equilibrium we can, by Le hatelier's principle, increase the concentration of either the alcohol or acid, as noted above. If either one is doubled, the theoretical yield increases to 85%. When one is tripled, it goes to 90%. But note that in the example cited the boiling point of the relatively nonpolar ester is only about 8 higher than the boiling points of the polar acetic acid and 1-butanol, so a difficult separation problem exists if either starting material is increased in concentration and the product is isolated by distillation. Another way to upset the equilibrium is to remove water. This can be done by adding to the reaction mixture molecular sieves, an artificial zeolite, which preferentially adsorb water. Most other drying agents, such as anhydrous sodium sulfate or calcium chloride, will not remove water at the temperatures used to make esters. A third way to upset the equilibrium is to preferentially remove the water as an azeotrope. The information in the table below can be found in any chemistry handbook table of ternary (threecomponent) azeotropes. The Ternary Azeotrope of Boiling Point 90.7 Percentage omposition of Azeotrope ompound Boiling Point of Vapor Upper Lower Pure ompound Phase Layer Layer ( ) 1-Butanol n-butyl acetate Water These data tell us that the vapor that distills from a mixture of 1-butanol, n-butyl acetate, and water will boil at 90.7 and the vapor contains 8% alcohol, 63% ester, and 29% water. The vapor is homogeneous, but when it condenses, it separates into two layers. The upper layer is composed of 11% alcohol, 86% ester, and 3% water, but the lower layer consists of 97% water with only traces of alcohol and ester. If some ingenious way to remove the lower layer from the condensate and still return the upper layer to the reaction mixture can be devised, then the equilibrium can be upset and nearly 100% of the ester can be produced in the reaction flask. The Dean-Stark Apparatus shown below is one such solution. Esterfication using a carboxylic acid and an alcohol requires an acid catalyst. ften, the acid form of an ion-exchange resin is used. This resin, in the form of small beads, is a cross-linked

4 polystyrene that bears sulfonic acid groups on some of the phenyl groups. Essentially it is an immobilized form of p-toluenesulfonic acid, an organic-substituted sulfuric acid. This catalyst has the distinct advantage that at the end of the reaction it can be removed simply by filtration. Immobilized catalysts of this type are becoming more and more common in organic synthesis. 3-way connector Dean-Stark trap for removing water through azeotropic distillation. The apparatus shown, modeled after that of Dean and Stark, achieves the desired separation of the two layers. The mixture of equimolar quantities of 1-butanol and acetic acid is placed in the flask along with an acid catalyst. Stirring reduces bumping. The vapor, the temperature of which is 90.7, condenses and runs down to the sidearm, which is closed with a cork. The layers separate, with the denser water layer remaining in the sidearm while the lighter ester plus alcohol layer runs down into the reaction flask. As soon as the theoretical quantity of water has collected, the reaction is over and the product in the flask should be ester of high purity. TL You are required to run a TL to monitor the progress of the reaction. Plates should have three spots (or lanes) on the origin: one for the main organic starting material that is being transformed, one for a cospot (starting material and the reaction mixture), and one for the reaction mixture. Synthesis of Benzyl Acetate: H3 H 2 H H H 2 Acetic anhydride MW bp 139, den Benzyl Alcohol MW bp 205, den Benzyl Acetate MW bp 206, den To a reaction tube add 540 mg of benzyl alcohol and 510 mg of acetic anhydride and a boiling chip. Attach the empty distilling column as an air condenser. Reflux the resulting mixture for 1 h or more, then cool it to room temperature. Add 1 ml of ether (use the wet ether found in a supply bottle in each hood) and 1 ml of water, separate the organic layer. Wash the aqueous layer with 1 ml of ether. ollect the ether layers, wash with sodium bicarbonate (2 X 1 ml), water (2 x 1 ml), and sat'd sodium chloride solution (1 ml). Dry the ether layer with anhydrous sodium sulfate, remove the organic layer into a vial and evaporate the ether by blowing it off in a stream of N 2. Isolation and Purification: n a larger scale, the product would probably be isolated and purified by vacuum distillation, but

5 this is difficult to do on a microscale without severe losses of material and thus poor yields. Therefore, chromatography is used here for purification. Assemble a microscale chromatography column (see Lab Guide for review), being sure it is clamped in a vertical position. lose the valve, and fill the column with dichloromethane to the bottom of the funnel. Prepare a slurry of 1 g of silica gel in 4 ml of dichloromethane in a small beaker. Stir the slurry gently to get rid of air bubbles, and gently swirl, pour, and scrape the slurry into the funnel, which has a capacity of 10 ml. After some of the silica gel has been added to the column, open the stopcock and allow solvent to drain slowly into an Erlenmeyer flask. Use this dichloromethane to rinse the beaker containing the silica gel. As the silica gel is being added, tap the column with a glass rod or pencil so the adsorbent will pack tightly into the column. ontinue to tap the column while cycling the dichloromethane through the column once more. Next, drain the solvent just to the surface of the silica. Add 10 drops of H 2 l 2 to the product mixture and using a Pasteur pipet, add this solution to the column, letting it run into the adsorbent and stopping when the solution reaches the top of the silica. The product vial is rinsed twice with 0.5-mL portions of dichloromethane that are run into the column, with the eluent being collected in a tared reaction tube. The elution is completed with a few more mls of dichloromethane. You will need to collect several 1 ml fractions. Analyze these by TL using 50:50 hexane:h 2 l 2 spotting starting benzyl alcohol as a standard. Evaporate the dichloromethane under a stream of nitrogen in the hood, and remove the last traces by connecting the reaction tube to the vacuum. Since the dichloromethane boils at 40 and the product at 206, separation of the two is easily accomplished. Determine the weight of the product, and calculate the yield. The ester should be a perfectly clear, homogeneous liquid. Analyze your product by the method listed on your assignment slip, preparing the sample according to the instructions in the Lab Guide. Analysis In addition to TL analysis, you may be instructed to analyze your final product by IR or NMR. Analyze your sample according to your assignment sheet and the instructions on Sample Preparation in the Lab Guide. leaning Up: After drying, place the used silica gel in the solid waste bin. Any dichloromethane should be placed in the halogenated organic waste container. Post Lab Questions: 1. Write the reaction for the synthesis of benzyl acetate from a silver salt and a bromo compound. 2. Write the reaction for the synthesis of benzyl acetate from an alcohol and an acid chloride.

The Fragrance of Rum, Isobutyl Propionate

The 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 information

Prelab Reading Assignment: Laboratory Techniques in Organic Chemistry, 4 th Ed. Chapter 19

Prelab 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 information

NaBr, H2SO4 CH3CH2CH2CH2Br + NaHSO4 + H2O. 1-Bromobutane bp C den MW n 1.439

NaBr, 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 information

Experiment 12: Grignard Synthesis of Triphenylmethanol

Experiment 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 information

The Friedel-Crafts Reaction: 2-(4-methylbenzoyl)benzoic acid

The 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 information

ORGANIC SYNTHESIS: MICROWAVE-ASSISTED FISCHER ESTERIFICATION

ORGANIC 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 information

Exp't 141. Exp't 141

Exp'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 information

Experiment 11: Dehydration of Cyclohexanol

Experiment 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 information

R C OR' H 2 O carboxylic acid alcohol ester water side product

R 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 information

SYNTHESIS 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 ) 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 information

In some cases, even an individual ester smells similar to a natural aroma. Some examples include:

In some cases, even an individual ester smells similar to a natural aroma. Some examples include: What are Esters? Many of the compounds that contribute to the flavors and aromas in fruits and flowers are esters. Natural flavors and aromas result from complex mixtures of many compounds, esters being

More information

The Synthesis of Triphenylmethano. will synthesize Triphenylmethanol, a white crystalline aromatic

The 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 information

Exp t 144 Synthesis of N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF"

Exp 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 information

Expt 7: Preparation of Isobutyl Propionate (or Isobutyl Propanoate)

Expt 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 information

Synthesis of Benzoic Acid

Synthesis 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 information

3. Two unknown samples are found to have the same R f value under identical TLC conditions. Are they the same compound? Explain.

3. Two unknown samples are found to have the same R f value under identical TLC conditions. Are they the same compound? Explain. I. Techniques in Organic Lab and TLC Analysis a. Thin-Layer Chromatography 2. A TLC plate displays the compound spot approximately 3.2 cm above the base line upon visualization; the solvent ran 4.1 cm

More information

CH 241 EXPERIMENT #6 WEEK OF NOVEMBER 12, NUCLEOPHILIC SUBSTITUTION REACTIONS (S N 1 and S N 2)

CH 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 information

Chem 102b Experiment 14: Part II Revised Preparation of Esters

Chem 102b Experiment 14: Part II Revised Preparation of Esters http://www.chem.arizona.edu/courseweb/981/chem102b1/fisher_esterification.html Purpose of the Experiment: Chem 102b Experiment 14: Part II Revised Preparation of Esters Students will be given alcohols

More information

Preparation of an Ester Acetylsalicylic Acid (Aspirin)

Preparation 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 information

Sodium Borohydride Reduction of Benzoin

Sodium 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 information

Wavenumbers. Infrared spectrum of 6-ethoxycarbonyl-3,5-diphenyl-2-cyclohexenone, KBr. Enamine Reactions: 2-Acetylcyclohexanone

Wavenumbers. 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 information

36B-BioOrganic Modifications for Technique Experiments. Technique of Thin-Layer Chromatography

36B-BioOrganic Modifications for Technique Experiments. Technique of Thin-Layer Chromatography 36B-BioOrganic Modifications for Technique Experiments Technique of Thin-Layer Chromatography Experiment Title: Applying TLC As A Method to Monitor the Multistep Synthesis of Aspirin You will be using

More information

Experiment DE: Part II Fisher Esterification and Identification of an Unknown Alcohol

Experiment 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 information

REACTIONS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase.

REACTIONS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase. CHEM 51LD EXP #2 FALL 2013 SYNTHESIS F ENANTIPURE ALCHLS AND ESTERS USING A LIPASE-BASED KINETIC RESLUTIN REACTINS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase.

More information

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. 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 information

CHMA2000 EXPT 7: The Physical and Chemical Properties of Alcohols

CHMA2000 EXPT 7: The Physical and Chemical Properties of Alcohols CHMA2000 EXPT 7: The Physical and Chemical Properties of Alcohols Objectives: At the end of this experiment you should be able to: 1. Understand the physical and chemical properties of alcohols 2. Understand

More information

Lab 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 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 information

CHEMISTRY Organic Chemistry Laboratory II Spring 2019 Lab #2: Grignard Reaction: Preparation of Triphenylmethanol

CHEMISTRY 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 information

Expt 10: Friedel-Crafts Alkylation of p-xylene

Expt 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 information

P1. SEPARATION OF ORGANIC COMPOUNDS MIXTURE

P1. SEPARATION OF ORGANIC COMPOUNDS MIXTURE P1. SEPARATION OF ORGANIC COMPOUNDS MIXTURE Objectives: to train basic organic laboratory techniques to learn basic procedures for isolation and purification of organic compounds to use acid-base chemistry

More information

Chemistry 283g Experiment 4

Chemistry 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 information

2. Synthesis of Aspirin

2. 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 information

Nucleophilic 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 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 information

5.37 Introduction to Organic Synthesis Laboratory

5.37 Introduction to Organic Synthesis Laboratory MIT pencourseware http://ocw.mit.edu 5.37 Introduction to rganic Synthesis Laboratory Spring 2009 For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms. URIECA

More information

12AL Experiment 11 (3 days): Nucleophilic Substitution Reactions

12AL 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 information

PREPARATIVE TASK GRAND PRIX CHIMIQUE PETNICA SCIENCE CENTER, VALJEVO, SERBIA 9 TH -14 TH OCTOBER 2017

PREPARATIVE TASK GRAND PRIX CHIMIQUE PETNICA SCIENCE CENTER, VALJEVO, SERBIA 9 TH -14 TH OCTOBER 2017 GRAND PRIX CHIMIQUE PETNICA SCIENCE CENTER, VALJEVO, SERBIA 9 TH -14 TH OCTOBER 2017 PREPARATIVE TASK Preparation of p-nitroacetanilide Preparation of vanillyl alcohol SUPPORTED BY Serbian Chemical Society

More information

Chemistry 262 Laboratory Experiment 3: Derivatization of the Grignard Product Formation of Ethyl and Propyl Benzoate 2/01/18, 2/08/18

Chemistry 262 Laboratory Experiment 3: Derivatization of the Grignard Product Formation of Ethyl and Propyl Benzoate 2/01/18, 2/08/18 Chemistry 262 Laboratory Experiment 3: Derivatization of the Grignard Product Formation of Ethyl and Propyl Benzoate 2/01/18, 2/08/18 Objectives Explore methods of carrying out esterification reactions.

More information

GRIGNARD REACTION Synthesis of Benzoic Acid

GRIGNARD 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 information

Experiment # 13 PREPARATION OF ASPIRIN

Experiment # 13 PREPARATION OF ASPIRIN Experiment # 13 PREPARATION OF ASPIRIN Objective In this experiment you will synthesize acetyl salicylic acid (aspirin), determine the limiting reagent, and then determine the theoretical and percent yields

More information

University 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 * 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 information

2 (CH 3 CH 2 ) 2 NH diethylamine

2 (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 information

Experiment 8: Chlorination of 1-Chlorobutane

Experiment 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 information

Review Questions for the Chem 2315 Final Exam

Review Questions for the Chem 2315 Final Exam Review Questions for the Chem 2315 Final Exam These questions do not have to be turned in, and will not be graded. They are intended to help you review the material we have covered in the lab so far, and

More information

Experiment 1: Extraction and Thin Layer Chromatography

Experiment 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 information

6. Extraction. A. Background. (a) (b) (c) Figure 1. Mixing of Solvents

6. 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 information

Chromatography: Thin-Layer Chromatography (TLC) & Column Chromatography

Chromatography: Thin-Layer Chromatography (TLC) & Column Chromatography Chromatography: Thin-Layer Chromatography (TLC) & Column Chromatography Part 1, p. 184: Separation of spinach pigments by TLC. (4 th Ed. P. 180) Part 2, p. 192: Separation of Fluorene and Fluorenone by

More information

Exp t 125. Oxidation of Borneol to Camphor. Reduction. Camphor. Borneol. Isoborneol

Exp t 125. Oxidation of Borneol to Camphor. Reduction. Camphor. Borneol. Isoborneol Exp t 125 Oxidation of Borneol to Camphor Adapted by and R. Minard (Penn State Univ.) from Introduction to Organic Laboratory Techniques: A Microscale Approach, Pavia, Lampman, Kriz & Engel, 1989. Revised

More information

Experiment 3: Preparation of Lidocaine

Experiment 3: Preparation of Lidocaine 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

More information

Exp t 111 Structure Determination of a Natural Product

Exp 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 information

REACTIONS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase.

REACTIONS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase. CHEM 51LD EXPERIMENT 2 SYNTHESIS F ENANTIPURE ALCHLS AND ESTERS USING A LIPASE-BASED KINETIC RESLUTIN REACTINS: Reduction of a ketone, acetylation of an alcohol, and a kinetic resolution using a lipase.

More information

Experiment 12 Grignard Reaction; Preparation of Triphenylcarbinol

Experiment 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 information

The Grignard Reaction: Synthesis of 4,4-Diphenyl-3-buten-2-one

The Grignard Reaction: Synthesis of 4,4-Diphenyl-3-buten-2-one Background The Grignard Reaction: Synthesis of 4,4-Diphenyl-3-buten-2-one The Grignard reaction is a classic method of carbon-carbon bond formation. Compounds that contain carbonyl functions react readily

More information

EXPERIMENT #1 SEPARATION AND RECOVERY OF ORGANIC COMPOUNDS, THIN LAYER CHROMATOGRAPHY, COLUMN CHROMATOGRAPHY, CRYSTALLIZATION AND MELTING POINTS

EXPERIMENT #1 SEPARATION AND RECOVERY OF ORGANIC COMPOUNDS, THIN LAYER CHROMATOGRAPHY, COLUMN CHROMATOGRAPHY, CRYSTALLIZATION AND MELTING POINTS EXPERIMENT #1 SEPARATION AND RECOVERY OF ORGANIC COMPOUNDS, THIN LAYER CHROMATOGRAPHY, COLUMN CHROMATOGRAPHY, CRYSTALLIZATION AND MELTING POINTS Overview In the first few weeks of this semester you will

More information

Experiment 8 Synthesis of Aspirin

Experiment 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 information

Expt 9: The Aldol Condensation

Expt 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 information

PHYSICAL CONSTANTS: MELTING POINTS, BOILING POINTS, DENSITY

PHYSICAL 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 information

Nitration of Bromobenzene by Electrophilic Aromatic Substitution

Nitration of Bromobenzene by Electrophilic Aromatic Substitution Nitration of omobenzene by lectrophilic Aromatic Substitution Part A, p. 515: Nitration procedure. (p. 504, 4 th d) Part B, p. 517: TLC. (p. 506, 4 th d) Part C, p. 518: Column chromatography. (p. 507

More information

Experiment 1: Preparation of Vanillyl Alcohol

Experiment 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 information

Multistep Synthesis of 5-isopropyl-1,3-cyclohexanedione

Multistep Synthesis of 5-isopropyl-1,3-cyclohexanedione Multistep Synthesis of 5-isopropyl-1,3-cyclohexanedione The purpose of this experiment was to synthesize 5-isopropyl-1,3-cyclohexanedione from commercially available compounds. To do this, acetone and

More information

Experiment 7 - Preparation of 1,4-diphenyl-1,3-butadiene

Experiment 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 information

Thin Layer Chromatography

Thin Layer Chromatography Introduction Thin Layer Chromatography Chromatography is an effective and very useful method for separation and purification of organic compounds that can be used even for complex mixtures. Chromatography

More information

Dehydration of Alcohols-Gas Chromatography

Dehydration of Alcohols-Gas Chromatography Dehydration of Alcohols-Gas Chromatography OBJECTIVE In this lab, we will examine the phosphoric acid catalyzed dehydration of 2-methylcyclohexanol. Gas chromatography will be used to monitor the outcome

More information

Minneapolis Community and Technical College. Separation of Components of a Mixture

Minneapolis 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 information

Experiment #2: Piperine - Synthesis and Isolation of a Natural Product

Experiment #2: Piperine - Synthesis and Isolation of a Natural Product Experiment #2: Piperine - Synthesis and Isolation of a Natural Product INTDUCTIN Piperine is the naturally occurring alkaloid that gives the spice black pepper its characteristic biting taste. The stereoselective

More information

Experiment 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 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 information

Green Chemistry in the Undergraduate Organic Laboratory: Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay

Green 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 information

LAB 17: SYNTHESIS OF BANANA OIL: REACTIONS OF ALCOHOLS: FISCHER ESTERIFICATION

LAB 17: SYNTHESIS OF BANANA OIL: REACTIONS OF ALCOHOLS: FISCHER ESTERIFICATION LAB 17: SYNTESIS F BANANA IL: REATINS F ALLS: FISER ESTERIFIATIN PURPSE: To synthesize isoamyl acetate by Fischer Esterification. To purify a liquid by simple distillation. SAFETY NERNS: Always wear safety

More information

EXPERIMENT 7 - Distillation Separation of a Mixture

EXPERIMENT 7 - Distillation Separation of a Mixture EXPERIMENT 7 - Distillation Separation of a Mixture Purpose: a) To purify a compound by separating it from a non-volatile or less-volatile material. b) To separate a mixture of two miscible liquids (liquids

More information

Chlorobenzene from Aniline via the Sandmeyer Reaction. August 21, By ParadoxChem126. Introduction

Chlorobenzene 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 information

As you can see from the reactions below for the reduction of camphor, there are two possible products, borneol and isoborneol.

As you can see from the reactions below for the reduction of camphor, there are two possible products, borneol and isoborneol. E19-1 Experiment 19 Fig. 19-1 REDUTIN WIT NaB 4 : STERI AND NJUGATIN EFFETS (3 Experiments) erbert. Brown (1912-2004) Received Nobel prize for synthetic organic chemistry work with boron compounds. http://nobelprize.org/chemistry/laureates/1979/brown-autobio.html

More information

Introductory Remarks:

Introductory 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 information

Expt 6: Preparation of Lidocaine, Part 1

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 information

Free Radical Chlorination

Free 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 information

Ester 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 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 information

METHOD 3520C CONTINUOUS LIQUID-LIQUID EXTRACTION

METHOD 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 information

Cl 2(g) + NaCl + H 2 O. light. 2Cl. Once formed, the chlorine radical can react with the heptane as shown below: + Cl

Cl 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 information

Title of experiment and short description of the purpose of the experiment.

Title of experiment and short description of the purpose of the experiment. The Laboratory Notebook for Chem 267 and 268. Use only the required notebook, one that allows a copy of each page to be made and torn out. The copy is given to the TA for grading and the original is kept

More information

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester

4023 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 information

Experiment 24. Chemical recycling of poly(ethylene) terephthalate (PET)

Experiment 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 information

Chapter 5. Chemical Extraction

Chapter 5. Chemical Extraction 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 : -

More information

To understand concept of limiting reagents. To learn how to do a vacuum filtration. To understand the concept of recrystallization.

To 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 information

6. Extraction. A. Background. (a) (b) (c) Figure 1. Mixing of Solvents

6. 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 information

Synthesis of Frambinone by Aldol Condensation and Catalytic Hydrogenation

Synthesis of Frambinone by Aldol Condensation and Catalytic Hydrogenation Experiment C Synthesis of Frambinone by Aldol Condensation and Catalytic ydrogenation Reading: rganic Chemistry by Marc Loudon, 5th ed., pp. 1063-1066 (22.4), 1100-1101 (22.9). Frambinone, otherwise known

More information

Experiment 2 - Using Physical Properties to Identify an Unknown Liquid

Experiment 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 information

DEHYDRATION OF ALCOHOLS-GAS CHROMATOGRAPHY

DEHYDRATION OF ALCOHOLS-GAS CHROMATOGRAPHY DEHYDRATION OF ALCOHOLS-GAS CHROMATOGRAPHY OBJECTIVE In this lab, one will examine the phosphoric acid catalyzed dehydration of 2-methylcyclohexanol. Gas chromatography will be used to monitor the outcome

More information

Aspirin Lab By Maya Parks Partner: Ben Seufert 6/5/15, 6/8/15

Aspirin Lab By Maya Parks Partner: Ben Seufert 6/5/15, 6/8/15 Aspirin Lab By Maya Parks Partner: Ben Seufert 6/5/15, 6/8/15 Abstract: This lab was performed to synthesize acetyl salicylic acid or aspirin from a carboxylic acid and an alcohol. We had learned in class

More information

Review Experiments Formation of Polymers Reduction of Vanillin

Review 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 information

+ X base) CH 2 X. R enolate anion

+ X base) CH 2 X. R enolate anion Exp't 13 (Adapted by Modi, Monarch, Perriello, Pohland, Minard and Walton (PSU '91-'92) from D Thompson and P. Reeves, "Phase-transfer-catalyzed Alkylation of Ethyl Acetoacetate and Diethyl Malonate",

More information

Acid-Base Extraction

Acid-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 information

Chemistry 283g- Experiment 4

Chemistry 283g- Experiment 4 EXPEIMENT 4: Alkenes: Preparations and eactions elevant sections in the text: Fox & Whitesell, 3 rd Ed. Elimination eactions of Alcohols: pg. 426-428, 431-432 Electrophilic Addition to Alkenes: pg. 484-488,

More information

CHEM51LC PROJECT DETERMINATION OF DIASTEREOSELCTIVITY USING THERMODYNAMIC VERSUS KINETIC CONTROLLED REDUCTION PROCEDURES: A REDUCTION

CHEM51LC PROJECT DETERMINATION OF DIASTEREOSELCTIVITY USING THERMODYNAMIC VERSUS KINETIC CONTROLLED REDUCTION PROCEDURES: A REDUCTION CHEM51LC PROJECT DETERMINATION OF DIASTEREOSELCTIVITY USING THERMODYNAMIC VERSUS KINETIC CONTROLLED REDUCTION PROCEDURES: A REDUCTION of 4-tert-BUTYLCYCLOHEXANONE REACTION: Oxidation of an Alcohol, Reductions

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 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 information

Honors Cup Synthetic Proposal

Honors Cup Synthetic Proposal onors up Synthetic Proposal Section: 221 Group Members: Shahid Ali, Jamuna Kesavan, harles Weidle, Pooja Desai, Suellen Yin Title: Synthesis of Vanillin: Mmmm What s that Aroma? Introduction: Vanillin

More information

General Chemistry I CHEM-1030 Laboratory Experiment No. 2 Physical Separation Techniques

General 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 information

Experiment 1: The Borohydride Reduction of 9-Fluorenone to 9-Fluorenol

Experiment 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 information

METHOD 3510B SEPARATORY FUNNEL LIQUID-LIQUID EXTRACTION

METHOD 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 information

Limiting Reagent Synthesis of Aspirin Thomas M. Moffett Jr., SUNY Plattsburgh, 2007.

Limiting 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 information

Oxidation of Alcohols: Oxidation of Borneol to Camphor

Oxidation 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 information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Nucleophilic Addition to Carbonyl: Grignard Reaction with a Ketone

Nucleophilic 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 information