In the process of performing a synthesis that include and aromatic ring there are several characteristics that need to taken into consideration such as, are there any substituents attached to the aromatic ring and if so, the type of substituent is important. Depending on the substituent that is bonded to the aromatic ring affects the position of additional substituents that are added. The substituents that are present on the aromatic ring can be identified as either as activating groups or deactivating groups. Activating groups direct the substituent being added to the ortha or para position, where as the deactivating directs to the meta position (Substituent Effects, n.d). Activating groups are the substituents that act as electron donators; …show more content…
This is the addition of bromine. As stated before in order to get the results wanted some times the use of a protection group is required and this is conducted before the bromination. If a protection group is utilized that mean and deprotection group is required, which does exactly what it sounds like and removes the protection group. The results are an aromatic with and aromatic ring with its original substituent in addition to the newly added …show more content…
Instead adding bromine to just the para position it would add it to both ortho positions and the para position. Acetanilide was not synthesized by refluxing a mixture of aniline and acetic anhydride because the high temperature might have caused the synthesis of a diacetylated product instead. Also the reason that sodium hydroxide could not be used instead of sodium acetate is because the sodium hydroxide would react with the acetic anhydride and consume it, preventing the acetic anhydride from reacting with the aniline. This is explained by C4H6O3 + NaOH → C2H4O2 + C2H3NaO2. Referring to the proton NMR of acetanilide in the lab manual, the first peak from the right represents the protons on the methyl group bonded to the carbonyl. The second peak from the right represents the proton on the aromatic ring directly across from the substituent or the 4th carbon on the ring. The third peak from the right represents the protons on the 3rf and 5th carbon of the ring. The fourth peak represent the protons on the 2nd and 6th carbons on the ring and the last peak all the way to the left represents the proton bonded to the nitrogen. The proton NMR for p-bromoacetanilide and p-bromoaniline will both have three peaks. For p-bromoacetanilide there will be a peak a approximately 2.0 ppm for the protons on the
After 28 minutes, the mixture stopped boiling, and approximately 4.5 ml of bromobenzene was added drop by drop in the mixture, and color of the mixture was turned light brown orange. Then, the phenylmagnesium bromide was cooled in ice bath for a few minutes, and 10 ml of anhydrous diethyl ether was added in the mixture by using the syringe. After that, approximately 2.3 ml of methyl benzoate was added to the reaction, and it was added slowly slowly because the reaction was exothermic which needed to be cool in order to maintain a gentle reflux. Once all the methyl benzoate solution was added, the heating mantle was removed from the reaction flask and was cooled to the room temperature. During the reaction, a milky white salt began to precipitate, and the reaction flask was swirled for ten minutes until most of the reaction became visibly subdivided.
Analyzing the neutral form of levothyroxine, there are three sites which have the possibility of being deprotonated. Deprotonation refers to the loss of a proton, or a hydrogen, by another chemical. For a site to be completely deprotonated and exist solely in that form, the base with which it is interacting must have a pKa at least three orders greater than that of the site on the molecule. Each of these three sites has a different relative acidity due to the structure of
The purpose of this lab is to determine the specific isomer of the bromovanillin produced. In this experiment, vanillin is brominated to produce a mixture of isomers or one single isomer of bromovanillin. The possible product(s) formed are 2-bromovanillin, 5-bromovanillin, and 6-bromovanillin, as seen in Figure 1.1 By utilizing the bromination process of vanillin, one bromovanillin isomer can be formed as a result. As the starting material, vanillin can work with various electrophilic aromatic substitution reactions, due to the presence of aromatic double bonds within the structure.
This helps to indicate whether or not the reaction follows Markovnikov’s Rule, which states that the electrophile (E+) will add to the carbon involved in a double bond that produces the most stable carbocation. If the rule is followed, the reaction will proceed according to the mechanism in Figure 1. In the silver nitrate test, the alkyl bromide is added to AgNO3. The rate of precipitation with 2° should be faster than the solution with the 1° alkyl halide. In the sodium iodide test, the alkyl halide is added to sodium iodide in acetone.
Discussion In this experiment, anthracene and maleic anhydride were reacted in solution to produce a single organic product in crystal form. Anthracene is composed of a 3 carbon rings where the first ring has a 3 pi bonds while the other two has 2. Also, the double bonds are separated by single sigma bonds, which conjugate the double bond. Maleic anhydride has a five-membered ring with ring’s oxygen atoms bonded to two acyl group, ester R-COO.
The reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
Chem 51 LB Experiment 3 Report Scaffold: Bromination of Trans-Cinnamic Acid 1. The goal of this experiment was to perform a halogenation reaction through the addition of two bromides from pyridinium tribromide. This was accomplished by reacting trans-cinnamic acid with pyridinium tribromide. After the reaction took place, melting point analysis was conducted to find out the stereochemistry of the product, which could either be syn-addition, anti-addition, or syn + anti-addition. 2.
The purpose of this experiment was to prepare an unknown Grignard reagent and then identify the product by molecular weight and melting point. An IR reading was taken to further identify and validate what product was formed. DISCUSSION AND CONCLUSION Organometallic compounds consist of a carbon that is attached to a metal. The carbon atoms are strongly nucleophilic because of a partial negative charge that they carry.
Experiment 12: Dehydrobromination Discussion In this experiment, a double elimination reaction was performed on meso-stilbene dibromide, to form diphenylacetylene by eliminating two hydrogen and two bromine atoms in he presence of potassium hydroxide. The product was filtered and identified by comparing melting point data, and percent yield was calculated. Since an E2 reaction was performed in this experiment, the ideal conformation for the hydrogen and bromine would have been anticoplanar. However, since the phenyl groups were bulky and the atom was not symmetric, the hydrogen and bromine could at best be antiperiplanar.
Next, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.
In this experiment rate of reaction with different reactants concentration: KI (0.010 M), KBrO3 (0.040 M), and HCl (0.10 M) will be observed. So, this is reaction between iodide and bromate ion under acidic conditions: 6 I- (aq) +BrO3-(aq)+ H+(aq)→ 3I2(aq) + Br-(aq)+ 3H2O The end of the reaction, will be determined by observing color change of solution. Thus, solution should shange color to blue.
Experiment 2 Report Scaffold (Substitution Reactions, Purification, and Identification) Purpose/Introduction 1. A Sn2 reaction was conducted; this involved benzyl bromide, sodium hydroxide, an unknown compound and ethanol through reflux technique, mel-temp recordings, recrystallization, and analysis of TLC plates. 2. There was one unknown compound in the reaction that was later discovered after a series of techniques described above.
The Wittig reaction is valuable reaction. It has unique properties that allows for a carbon=carbon double bond to form from where a C=O double bond used to be located. Creating additional C=C double bonds is valuable due to its use in synthesis. The Wittig reaction will allow the synthesis of Stilbene (E and Z) from a Benzaldehyde (Ketcha, 141).
Bromination is a type of electrophilic aromatic substitution reaction where one hydrogen atom of benzene or benzene derivative is replaced by bromine due to an electrophilic attack on the benzene ring. The purpose of this experiment is to undergo bromination reaction of acetanilide and aniline to form 4-bromoacetanilide and 2,4,6-tribromoaniline respectively. Since -NHCOCH3 of acetanilide and -NH2 of aniline are electron donating groups, they are ortho/para directors due to resonance stabilized structure. Even though the electron donating groups activate the benzene ring, their reactivities are different and result in the formation of different products during bromination.
To analyze the acetanilide product of the reaction, 1H NMR and IR were used. Results, Discussions, and Conclusions In this experiment, acetanilide was synthesized via nucleophilic acyl substitution from both acetic anhydride and aniline. During this reaction, aniline acts as the nucleophile and acyl (CH3CO-) group from acetic anhydride acts as the electrophile.