formation typically forms the major product because it takes less kinetic energy to be formed due to secondary orbital interactions with the substituents in transition states (Hunt). The rule that guides this principle is typically referred to as the “Alder Endo Rule”. In instances where the diene and dienophile are staggered and they must reach for each other in order to form the product‚ the exo product is formed (Hunt).
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polynuclear aromatic hydrocarbons. 2. Identify structures that are products of the following reactions: a. Grignard reaction including identification of the nucleophile. b. Conversion of nitriles into carboxylic acids and acid derivatives c. Diels-Alder reactions d. Reduction of aldehydes and reagents used for that reaction. e. Fischer esterification including identification of nucleophile‚ catalyst‚ and leaving group. f. Reaction of acid chlorides to produce alcohols. g. Reaction of carbonyl
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The Diels-Alder product obtained in this experiment had a measured melting point of 154°C‚ which has a discrepancy of 11degrees from the literature value of 165°C. These values show an experimental flaw in the process of drying the solid product obtained from the vacuum filtration portion of the method of experimentation. Because the product was not fully dry during the melting point portion of the experiment‚ the melting point results were skewed. The reactants and solvents in the reaction each
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steps. The first step involves the acylation of aniline with maleic anhydride to give maleanilic acid 1. I n the second step maleanilic acid undergoes the Michael addition of aniline and cyclization to yield I-phenyl-3-pl~enylaminopyrrolidine-2‚5dione 2 (Method A). Compound 2 can also he obtained in one step by using commercially available maleanilic acid (Merck) or‚ albeit in slightly lower overall yield‚ by refluxing maleic anhydride and aniline in 12molar ratio in acetic acid (Method B) (Fig
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0.947g/ml x 5ml = 4.739g Therefore moles = mass/molar mass = 4.739g/98.15g mol-1 = 0.0483 moles Mass pyrrolidine = 0.866g/mol x 4.0 ml = 3.464g Therefore moles = mass/molar mass = 3.464 / 71.11g mol-1 Addition of the acetic anhydride Enamine Acetic Anhydride Molecular formula: C10H9N Molecular formula: C4H6O3¬
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Otto Diels Otto Diels was a German chemist who was born 25th January 1876 in Hamburg‚ Germany. Otto attended the University of Berlin in 1899 and remained there as a Professor from 1906 to 1916‚ in this time he discovered a new oxide of carbon - carbon suboxide C3O2 which was refined from the work of Benjamin Brodie. Carbon suboxide is used to prepare malonate ions CH2(COO)22− and to help fur dye better. Later Diels joined the University of Kiel from 1916 to 1950. in 1922 he developed a new method
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PRE-LAB ASSIGNMENT 1. Maleic acid is the cis version and fumaric acis is the trans version of butenedioic acid. 2. 3. See attached paper. 4. Maleic anhydride is the compound that crystalizes in part A in the experiment. 5. HCl acts as a catalyst to break one of the carbonyl group in the maleic acid which rotates the structure to form a trans structure of the butonal acid which is the fumaric acid. And it does so by donating its protons. 6. Maleic acid Chronic effects: mutagenic
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University‚ Korea (Received : May. 20‚ 2009‚ Revised : Jun. 02‚ 2009‚ Accepted : Jun. 12‚ 2009) Abstract : 2-Acetylcyclohexanone was synthesized by acylation reaction of acidic anhydride using enamine as organiocatalyst instead of a strong base‚ NaOH‚ resulting in milder reaction conditions. The reaction was conducted in toluene and direct distillation of the reaction mixture before hydrolysis was leaded to a high yield of the pyrrolidine enamine. This condition was leaded good yields (73.6%) without
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Stereochemistry of Butenedioic Acid Objective: To study the interconversion of two geometric isomers‚ maleic acid (cis isomer) to fumaric acid (trans isomers)‚ the differences in physical properties between this pair of cis-trans isomers and determine the stereochemistry of addition of bromine to butenedioic acid. Chemicals and Apparatus: 2 grams of maleic acid‚ 10 cm3 of concentrated hydrochloric acid‚ 10 cm3 of bromine water[1]‚ one 50 cm3 beaker‚ one 100 cm3 beaker‚ one 250 cm3
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6 Synthesis of an Alkaloid: Pseudopelletierine (two weeks) ............................................................9 Synthesis of 5‚5-dimethyl-1‚3-cyclohexanone ............................................................................11 Diels-Alder Syntheses of Polycyclic Compounds ......................................................................13 The Fischer Indole Synthesis: Preparation of 2-Phenylindole ...............................................16 Chemistry 3373f‚ Fall 2007
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