...Torres 1 Luis A. Torres Group #11 USC Chemistry 322b Formal Lab Report 6th November 2015 I. II. Enzymatic Resolution of 1-Phenylethanol and Diastereomer Analysis Objective/Abstract Enzymatic transesterification reaction was performed to study the resolution of diastereomers using 1H-NMR analysis. The stereo-selectivity of acylase I, an enzyme, for a 50:50 racemic mixture of 1-phenylethanol was determined. In the first of a two-step reaction, 1-phenylethanol was reacted with vinyl acetate with the help of acylase I to form an ester, unreacted 1-phenylethanol, and vinyl alcohol. The unreacted 1phenylethanol was separated from the ester by column chromatography and confirmed by thin-layer chromatography (TLC). In the second reaction, the unreacted 1-phenylethanol was reacted with (R)-(-)-acetoxyphenylacetic acid to form a diastereomer ester. In the latter reaction, four different 1-phenylethanol samples were used in order to compare 1HNMR data of the resulting diastereomer esters and determine which enantiomer of the 50:50 racemic mixture was preferred by acylase I. Those four samples were: (1) racemic 1-phenylethanol, (2) unreacted 1-phenylethanol, (3) (R)-1-phenylethanol, and (4) (S)-1phenylethanol. After 1H-NMR analysis, it was found that the (S)-1-phenylethanol was preferred by acylase I. III. Introduction and Background Information Scheme 1: Reaction of 1-phenylethanol with vinyl acetate in the presence of the enzyme acylase I to produce 1-phenylethyl...
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...POINT LISAS CAMPUS Esperanza Road, Brechin Castle, Couva www.utt.edu.tt LAB 1 Decomposition reaction Aim: Determination of the number of moles of water molecules of crystallization present in hydrated Magnesium Sulphate (MgSO4.xH2O) Apparatus: Mass balance, test tube, test tube holder, heat-proof mat and bunsen burner. Reagents: Hydrated sodium carbonate. Theory: Chemical decomposition, analysis or breakdown is the separation of a chemical compound into elements or simple compounds. A more specific type of decomposition is thermal decomposition or thermolysis, which is caused by heat. ABA+B, the reaction is endothermic, since heat is required to break the chemical bonds. Most decomposition reaction require energy either in the form of heat, light or electricity. Absorption of energy causes the breaking of the bonds present in the reacting substance which decomposes to give the product. When a hydrated salt is heated it decomposes into a pure form of the salt and water. MgSO4.xH2O MgSO4 + H2O Procedure: Refer to Handout Results: A. Mass of test tube/g = 21.77 B. Mass of the tube and salt/g = 24.0 A table showing the mass of the test tube and salt after 3 consecutive heating: Heating | Mass of the test tube and salt/g | 1st | 23.96 | 2nd | 23.81 | 3rd | 23.81 | Calculations: G. Mass of anhydrous magnesium sulphate/g = F - A = 23.81 – 21.77= 2.04 H. Mass of water of crystallization evaporated/g...
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...SAFETY AND LABORATORY RULES for ORGANIC CHEMISTRY LABORATORIES Explanatory comments may be found below under Standard Operating Procedures APPROVED SAFETY GOGGLES MUST BE WORN AT ALL TIMES. NO FOOD, DRINKS OR SMOKING ARE ALLOWED. SHOES MUST BE WORN. No bare feet or thong sandals are allowed. WORK IS PERMITTED ONLY DURING SCHEDULED LABORATORY PERIODS. Work is not permitted in other laboratory periods unless space is available and written permission is obtained from your instructor. NO OPEN FLAMES ARE ALLOWED except as directed by the instructor. KNOW THE LOCATION OF FIRE EXTINQUISHERS, SAFETY EQUIPMENT, AND THE NEAREST EXIT. NO UNAUTHORIZED EXPERIMENTS MAY BE PERFORMED. DO NOT USE BROKEN OR CRACKED GLASSWARE. Check glassware before using it. NEVER TASTE OR SMELL CHEMICALS. AVOID CONTACT OF CHEMICALS WITH SKIN. The use of rubber gloves is recommended. DISPOSE OF CHEMICAL WASTE AS DIRECTED BY INSTRUCTOR. CLEAN YOUR WORK AREA AND PUT AWAY ALL EQUIPMENT AND GLASSWARE BEFORE LEAVING. Make sure equipment is put away in the correct locker - your personal locker or the common locker. PUT PAPER TRASH AND BROKEN GLASS IN TRASH CONTAINERS. KEEP INSTRUMENT ROOM CLEAN AND FREE OF PAPER. STANDARD OPERATING PROCEDURES IN THE ORGANIC CHEMISTRY LABORATORY Any student working in an unsafe manner may be dismissed from the laboratory by an instructor. Attitudes and Preparation Come to laboratory periods on time and mentally prepared by studying the experiment and planning...
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...Acetanilide is used as an inhibitor in hydrogen peroxide and is used to stabilize cellulose ester varnishes. intermediate and camphor synthesis, these were the established uses in intermediation. Acetanilide used in pharmaceutical and intermediates as a precursor in penicillin synthesis. The uses of this organic material have decreased over the past few years due to its toxicity. However, it is still used for some industrial purposes. It has application as an inhibitor in hydrogen peroxide and this compound is also used for stabilizing cellulose ester varnishes. It is applied in the intermediation in accelerator synthesis of rubber. The organic compound is used for manufacturing 4-acetamidobenzenesulfonyl chloride which is one of the key ingredients for producing sulfa drugs. This compound is used as a precursor for synthesizing pharmaceuticals like penicillin. it was experimentally used as a photographic developer in the The Preparation of Acetanilide and its physical and chemical properties. Acetanilide organic compound is synthesized in a reaction of acetic anhydride with aniline. This production is used in introductory lab classes of acetanilide organic chemistry....
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...817121% x 179.2 = 14.008 / 14.008 = 1.004 = 1 Oxygen 17.853837% x 179.2 = 31.994 / 15.999 = 1.999 = 2 C10H13NO2 [pic]--------------------------------------------------------------------------------------------------------------------- Degree of Unsaturation 2C + 2 + N - X - H = 5 2 --------------------------------------------------------------------------------------------------------------------- Functional Groups amide, aromatic, ether Tests melting point, solubility Physical Properties white crystalline powder, odorless Introduction Qualitative analysis in organic chemistry is used in the identification of unknown substances. Although there is not a rule of order when performing these tests it is more important to have a systemic approach. If the same general order is always used then the results will be more favorable. |General Scheme of Analysis | |A. Preliminary Test | |Note physical characteristics: solid, liquid, color, and odor....
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...Preparation of Grignard Reagents and the Preparation of 2-methyl-3-heptanol from 2-methylpropanal and Grignard Reagents II. Introduction Organometallic compounds are substances with a carbon-metal bond (structure 1); these metals may be Li, Na, Mg, Cu, Hg, Pd, or any other transition metal (Gilbert, Martin 639). Organometallic compounds with M representing MgBr are organomagnesium compounds, or more commonly Grignard reagents. Grignard reagents are unique due to their polarization. The carbon atom in the Grignard reagent is made electron-rich by the electropositive metal giving the carbon atom a partial negative charge (δ-), and the metal a partial positive charge (δ+). This unique charge distribution allows carbon to act as a nucleophile in chemical reactions. However, when carbon is bonded to a more electronegative atom, such as a halogen (structure 2) or to oxygen (structure 3), it acts as an electrophile in chemical reactions (Gilbert, Martin 639). Figure 1. Structure of an organometallic reagent (structure 1), an alkyl halide (structure 2), and a carbonyl compound (structure 3). * Due to the nucleophilic properties, organometallic compounds are commonly used in reactions to form new carbon-carbon bonds. Equation 1 is a general example of a reaction between an alkyl halide and an organometallic compound. Equation 2 is an example of a reaction of a carbonyl and an organometallic compound. In both reactions the nucleophilic carbon atom of the organometallic...
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...chromophore group and a salt forming group called anchoric group. In 1876, Otto witt put forth a theory as to correlate color with molecular structure (constitution). The theory is named'The Chromophore Auxochrome Theory' and its main postulates are, (i) The color of the organic compounds is due to the presence of certain multiple bonded groups called chromophores. Important chromophores are, O || . . . . . . –N = N –, – N —> O, –N = N –, C = O, C = S Azo Nitro Carbonyl Thio carbonyl [Chromophore-Greek word, Chroma = color, Phorein = to bear]. The presence of chromophore is not necessarily sufficient for color. To make a substance colored, the chromophore has to be conjugated with an extensive system of alternate single and double bonds as exists in aromatic compounds. The chromophore part of the colored substance (dye) absorbs some wavelengths from white light and reflects back the complementary color. A colored compound having a chromophore is known aschromogen. (ii) Certain groups, while not producing color themselves, when present along with a chromophore in an organic substance, intensify the color. Such color assisting groups are called auxochromes(Greek word, Auxanien = to increase; Chrome = color), i.e. they make the color deep and fast and fix the dye to the fabric. The auxochromes are acidic or basic functional groups. The...
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...CHAPTER 12 HYDROCARBONS 12.2 Alkenes Learning Outcomes At the end of this topic, students should be able to: a) Describe alkenes as unsaturated hydrocarbon with the general formula CnH2n, n≥2. (b) Draw the structures and name the compunds according to the IUPAC nomenclature for: i) straight chain and branched alkenes (parent chain ≤ C10) ii) cyclic alkenes (C3-C6) iii) simple dienes (C4-C6) 2 Learning Outcomes At the end of this topic, students should be able to: c) Show the preparation of alkenes through: i) dehydration of alcohols ii) dehydrohalogenation of haloalkanes d) Write the mechanism for c(i) e) State Saytzeff’s Rule. f) Deduce the major product of elimination reaction. 3 Alkenes - General formula CnH2n , n 2. - Functional group C=C double bond - Unsaturated hydrocarbon - C═C 1 σ bond and 1 π bond A B C=C A B Restricted rotation of carbon-carbon double bond causes cis-trans isomerism 4 Alkenes Cycloalkenes - General formula CnH2n-2 - Isomeric to alkynes CnH2n-2 Example : C4H6 CH2 CH CH2 Functional group isomerism CH CH3C – CCH3 5 Alkenes Common Names Of Alkenes Many older names for alkenes are still in use … example: CH2 CH3 CH2 ethene ethylene CH2 CH CH3 CH2 2–methylpropene isobutylene CH3 CH3 propene propylene C CH3 C CH CH2 2–methylbut-1,3-diene 6 isoprene Alkenes IUPAC...
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...N-methylmorpholine-N-oxide (NMMO) categorizes as a family of cyclic, aliphatic, tertiary amine oxides [287, 288]. Tertiary amine oxide systems were first patented by Graenacher and Sallmann in 1939 to dissolve cellulose for enhanced chemical processing [289]. However, Johnson, for the first time in 1969, introduced a cyclic mono(N-methylamine-N-oxide) compound to dissolve strong intermolecular hydrogen bonding networks (e.g., cellulose, wool, silk, hair, and feather), which are insoluble in commonly used solvents [290]. Since the late 1970s, the research on the dissolution of cellulose in NMMO was initiated when McCorsley and Varga [291] produced a highly concentrated yet economical cellulose solution by dissolving cellulose in a NMMO-water system. At that time, research on NMMO-cellulose tertiary systems was mainly focused on producing regenerated cellulose fiber that has applications in textiles and nonwovens, lyocell process, strengthening paper films, and paper coatings [287, 290, 292-294]. However, this technology has been recently introduced as a pretreatment method of lignocelluloses for improvement of either second-generation bioethanol [295-301] or biogas production [302-311]. Having a strong N-O dipoles, which acts as either ionic or donative and single bond, NMMO is capable of disrupting the hydrogen-bond networks of cellulose and building new hydrogen bonds between the polymer and the solvent (Fig. 9) [288, 292, 312]. Cellulose dissolution in NMMO leads to a tertiary...
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...CHEM 225 2015-16 Suggested Practice Problems from “Introduction to Organic Chemistry, 5th Ed.” The following problems are not intended for marks, but are highly recommended as a source of practice for you in preparation for the midterms and final exam, as many of your exam questions will follow a similar format. Also, keep in mind that as you progress in the questions for each chapter, so will the level of difficulty – DON’T get frustrated if you have to try the last questions of the chapter a few times to get it. Even though the answers can be found in the corresponding solutions manual, I strongly suggest that you attempt to work through these problems prior to consulting the answer guides. In my experience, the best way to succeed at organic chemistry is to practice, practice, practice! Memorization will not work and will soon become overwhelming. Do not try to do these all at once; the best plan of attack is to set aside an hour or two each week to work on these. If you grasp the concepts of this material, it will make for much easier problem solving in this course. If you have any difficulties or the answers are not clear (the same applies to anything in this course), do not hesitate to contact me at ghallett@stfx.ca or drop by my office (PSC 3025). Chapter 1 1.1-1.16, 1.17-1.19, 1.21-1.24, 1.26-1.32, 1.34, 1.35, 1.37, 1.39, 1.41-1.42, 1.44-1.46, 1.48, 1.501.53, 1.57, 1.60, 1.64, 1.66, 1.67 Chapter 2 2.1-2.10, 2.11, 2.14-2.17, 2.25-2.26, 2.28-2.29, 2.32-2...
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...Organic Chemical Reactions – an introduction. Here are two typical reactions involving organic chemicals: [pic] What does a reaction scheme like either of those above tell you? It tells you that the molecules or atoms to the left of the arrow will react together to give the molecule(s) on the right of the arrow when they are mixed together. Simplifying: [pic] The arrow implies the reaction goes to completion – all of chemicals A and B are used up to form new chemicals C and D. Note – it tells you nothing about how quickly they react – some reactions are fast, some are slow. You can say that if you leave it long enough you will reach a point where you have a mixture of C and D, and no A and B will be left. Some reactions do not go to completion – not all of A and B are converted to C and D, no matter how much time you give the mixture to react. These are equilibrium reactions and can be recognised from the two-way arrow: [pic] These reactions are reversible – when C and D have formed they can react together to re-form A and B. The precise amount of A + B and C + D that forms in an equilibrium reaction is governed by the equilibrium constant, Keq, for the reaction. A and B are the chemicals you start off with. You will hear them described in several ways – the reactants (i.e., the things that are reacting together), the reagents (same thing), the starting materials (obvious), the precursors (fancy name for starting materials)...
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...|Characteristic IR Absorption Frequencies of Organic Functional Groups | | |Type of Vibration |Characteristic Absorptions |Intensity | |Functional Group | |(cm-1) | | |Alcohol | | |O-H |(stretch, H-bonded) |3200-3600 |strong, broad | |O-H |(stretch, free) |3500-3700 |strong, sharp | |C-O |(stretch) |1050-1150 |strong | |Alkane | | |C-H |stretch |2850-3000 |strong | |-C-H |bending |1350-1480 |variable | |Alkene | | |=C-H |stretch...
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...CHEM 232 1. Organic Chemistry II Problem Set 12 Identify each of the following compounds as reducing or nonreducing sugars: H HO HO H HO CH2 O H OH H CH2OH OH B Nonreducing sugar (acetal) CHO H H E OH OH CH2OH CHO OH OH OH CH2OH H H G OH HO CH2OH O H H H OCH2CH3 H HO H OH OH CH2OH O H H H OH CH2 O C OH H CH2OH H OH H H O H HO A Reducing sugar (hemiketal) Nonreducing sugar (acetal and ketal) CH2OH C O OH OH CH2OH CH2OH HO OH H O H CH2OH H H H H F OH D Reducing sugar (hemiketal) Reducing sugar (aldose) Reducing sugar (aldose) Reducing sugar (ketose) 2. Which of the structures shown above are: a. Pyranose monosaccharides A and B b. Furanose monosaccharides D c. Tetroses E d. Aldopentoses F e. Ketopentoses G f. Disaccharides C 3. Give the Haworth formula for α-D-Glucopyranose. H HO H OH CH2OH O H H OH H OH 4. Complete the following reactions: a. CH3CH2CH(OH)CH2OH b. O HOCH2 C CH2OH HIO4 CH3CH2CHO + CH2=O OH O O AgNO3-NaOH NH3 HOCH2 CH C Ag0 OH HOCH2 C c. H H CHO OH OH CH2OH HIO4 3 HCO2H OH CHOH HOCH2 CH C d. O H CHO H H OH OH CH2OH HCN CN H H H OH OH OH CH2OH HO CN H OH OH CH2OH + CH2=O + H H e. H HO H CHO OH H OH CH2OH NaBH4 H2O H HO H CH2OH OH H OH CH2OH h. H HO f. HO H H CHO H OH OH CH2OH CHO 1. Br2/H2O 2. H2O2 Fe2(SO4)3 H H OH OH CH2OH g. CHO H OH H H OH OH CH2OH 3 PhNHNH2 CH NNHPh C H H NNHPh OH CH2OH O H H H OH OH H OH CH3OH H+ ...
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...group to a compound. The compound providing the acyl group is called the acylating agent. These are used to form aryl ketones. Because they form a strong electrophile when treated with some metal catalysts, acyl halides are commonly used as acylating agents. For example, Friedel-Crafts acylation uses acetyl chloride (ethanoyl chloride), CH3COCl, as the agent and aluminum chloride (AlCl 3) as a catalyst to add an ethanoyl(acetyl) group to benzene: The mechanism of this reaction is electrophilic substitution. Hydrolysis While solvolysis often refers to an organic chemistry context, hydrolysis is very common in inorganic chemistry, where aqua complexes of metal ions react with solvent molecules due to the Lewis acidity of the metal center. For example, aqueous solutions of aluminium chloride are acidic due to the aqua-aluminium complex losing protons to water molecules, giving hydronium ions which lowers the pH. In organic chemistry, hydrolysis reactions often give two fragments from an initial substrate. For example, the hydrolysis of amides give carboxylic acids and amines; the hydrolysis of esters give alcohols and carboxylic acids. Alcoholysis An example of a solvolysis reaction is the reaction of a triglyceride with a simple alcohol such as methanol or ethanol to give the methyl or ethyl esters of the fatty acid, as well as glycerol. This reaction is more commonly known as a transesterification reaction due to the exchange of the alcohol fragments. The reaction mechanism for...
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...[pic] Chemistry 2423 Exam 2A [pic] O Cimene – refers toseveral isomeric compounds. The Ocimenes are monoterpenes found within varity of plants fruits. Instructor : Dr. Pahlavan ORGANIC CHEM 2423 EXAM # 2A Sample(Chapters 5,6, and7) Name:__________________ Score DIRECTIONS- Please answer all questions in the space provided as completely and clearly as possible . Show all your work for the writing portions of the exam. PART I – Multiple Choice (3 points each) _____ 1. Species with unpaired electrons are called ___________________ . A. molecular ions B. free atoms C. radicals D. electrophiles _____ 2. Identify the type of the following reaction: [pic] A. elimination B. substitution C. addition D. rearrangement _____ 3. Consider the following reaction. Which species is the nucleophile? [pic] ( I ) ( II) ( III ) A. I only B. II only C. III only D. none of these _____ 4. This process occurs when both bonding electrons remain with one product fragment. A. homolytic bond breaking B. heterolytic bond breaking C. hemolytic bond formation D. radical formation _____5. ...
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