1. Write a mechanism for the Grignard reaction of benzophenone with phenylmagnesium bromide. Be as complete as possible and show electron flow for all steps.…
The literature value for the melting point range for Trans-9-(2-phenylethenyl)anthracene is 130-133 oC. The obtained range was lower than that at 120.3 to 123.8 oC. Because it is lower than the known value, this means the obtain product is not completely pure. Impurities in the compound can result in a decrease in the compounds melting point, which is observed here. The impurities could be 1-propanol due to an insufficient drying.…
In Part 1, an attempt to synthesize acteophenetidin crystals by amide synthesis was made. We began by removing the colored impurities from the p-Phenetidine (reddish-brown) by placing 2g of the sample in 38 mL of hydrochloric acid and heating the solution to boiling point. Upon reaching just below boiling point, decolorizing carbon was added to the solution, and the solution was allowed cooled for 2-3 minutes. The dark black solution was filtered through a gravity filtration system, leaving dark residue behind on the filter paper, and colorless to slightly pink liquid in the beaker. Then, 9 mL of sodium acetate buffer, to maintain a relatively constant pH and 1.8 mL of acetic anhydride were added to the solution, and then it was mixed and heated for about 5 minutes. Then, to induce crystallization, the beaker was placed in an ice bath. The slightly white, powdery crystals were collected using the Buchner funnel, and allowed to dry in the funnel and then on a watch glass.…
This particular Diels-Alder reaction exploits an interesting phenomenon. Although aromatic compounds do not normally participate in Diels-Alder reactions, the central ring in anthracene is reactive as a diene. Since all three rings of anthracene can not simultaneously have benzenoid character (Figure 1), the electrons in the pi system of the central ring react more like those of a standard diene. The reaction of the central ring in anthracene allows for the formation of two, independent benzene rings, as seen in the mechanism outlined in Figure 2.…
Grignard reagents are widely used in the synthesis of organic molecules and organometallic compounds. Grignard reagents are extremely reactive with Lewis acids such as water. Therefore, precautions were taken during the lab to ensure that the reaction was not ruined due to the presence of water, increase the percentage yield, and obtain more accurate results. These reactions tend to split into two groups:…
This experiment was preformed according to the methods described in the laboratory manual (Lehman, 134-135). To carry out the Diels-Alder reaction 1.00g of eucalyptus oil was dissolved with a 2.00ml ethyl ether. Assuming that 50% of the mass of the eucalyptus oil was the unknown diene, the mass of maleic anhydride needed to react with .50g of diene was calculated and added to the reaction mixture. The reaction mixture was than heated under gentle reflux, using a hot water bath for 45 minutes. After heating the reaction mixture, it was cooled to room temperature…
When it comes to organic chemistry and the synthesis of specific products there is an abundant amount of routes that can be taken and still get you the same result. For the following experiment, the main focus is the use of a cycloaddition reaction, also known as Diels-Alder. According to the lab manual, this reaction consists of the addition of a diene and a dienophile and that the Diels-Alder reaction builds stereospecific ring compounds with ease (Weldegirma 80). The reaction takes place between the two pi electrons from the dienophile and the 4 pi electrons from the diene; what happens is the bonds react together in order to form new single bonds because they are more stable, in terms of energetics (Diels-Alder Reaction). In order for the…
Marilyn Wooten PhD. marilyn.wooten@gmail.com 01T 7:30–11:20 am T/R Ray Still M.S. Raymond.still@gmail.com 02T 6:30 10:20 pm T/R *If you miss a lab you must email me and your lab instructor ASAP. You will have one week to make up the lab and it must be made up in one of the sections listed above. Prerequisites: Completion of or concurrent enrollment in CHE 3643. Course Outline: Simple and multistep synthesis of organic compounds. Text: There is NO text for this lab. Experimental procedures can be found on Blackboard Learn. https://learn.utsa.edu/ Lab notebooks: Instructor's discretion Grades: 60% lab reports 20% Midterm exam 20% Final exam o Exams will be over lab and lecture material. You may use your lab reports during the midterm and final Format of prelab: 1. Title of experiment 2. Abstract A short description of the experiment 3. Include reactions (with mechanism) if applicable. 4. Structures of reactants and products. (only organic compounds) http://www.sigmaaldrich.com Wikipedia also has information on chemical compounds but it is community maintained, so double check the information. 5. Table of physical constants for all chemicals (this includes products) Amount to be used, melting point, boiling point, MW, and density. o http://www.sigmaaldrich.com 6. Hazards of all chemical used in lab. (must be complete or you will be sent out)…
The experimental product yield is 0.28g (some solid left on the filter paper and some for the melting point measurement.)…
Diels Alder Reaction is the reaction of a diene with a species capable of reacting with the diene, the dienophile. A diene is a hydrocarbon that contains two carbon double bonds, while a dienophile is an electron-deficient alkene.…
The Diels-Alder reaction is one of the most powerful tools used in the preparation of important organic molecules. When two carbon-carbon double bonds are positioned next to one another, a conjugated diene is formed. Conjugated dienes undergo a cycloaddition reaction (also called pericyclic addition) with certain double bonds to afford cyclohexenes and related compounds. The reaction of Cyclopentadiene with Maleic anhydride is an example of a Diels-Alder reaction. This reaction forms a six-membered ring from two reagents: a conjugated "diene" (which provides four of the ring atoms) and a "dienophile" (which provides two of the ring atoms). In this case, the dienophile is Maleic anhydride and the diene is cyclopentadiene. The Diels-Alder reaction is facilitated by the presence of electron donating groups (EDG) on the diene and by the presence of electron withdrawing groups (EWG) on the dienophile. For instance, maleic anhydride is a very good dienophile because it contains two highly electron withdrawing carbonyl groups.…
In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.…
The purpose of these experiments is to create two different cyclic products using Diels-Alder reactions.…
The main goal of this lab was to create a Grignard reagent and then use that same reagent to produce a tertiary alcohol. This was accomplished by reacting the Grignard reagent with acetophenone. The end product was 1,1-diphenylethanol. Its recorded melting point range was 80°C-81°C, which is the same as its literature value. This means that there was no or very little impurity in the recrystallization process…
In the first part of this experiment acetic anhydride was used to prepare acetanilide which could then be readily brominated to form a mono-brominated product, with the bromine positioned at either the ortho, meta or para position on the aromatic ring. Acetic anhydride is very reactive towards nucleophiles and this reactivity is the result of the difference in electronegativities of the carbon and oxygen atoms that are bonded in acetic anhydride. This difference in electronegativities causes one of the carbonyl groups in acetic anhydride to break its carbon-oxygen double bond with the oxygen atom taking the pair of electrons from the pi bond and results in a negative charge on oxygen and a positive charge on carbon. The positive charge on carbon is then stabilized by the donation of a lone pair of electrons from oxygen, which is attached to both of the carbonyl groups in acetic anhydride, and results in the formation of an O=C bond with the oxygen containing a positive charge. The formation of the oxygen with the positive charge causes the electrons in C-O bond to be pulled more closely to the oxygen and results in the carbon on the unaltered carbonyl group to be very electron deficient and this is the cause of the reactivity of acid anhydrides.…