I. Chemical reactions: Consultation/reference to literature should be considered as the use of well documented chemical reactions for the synthetic route will lead to higher yields and less impurities. II. Catalysts: The use of a catalyst can be an advantage however it may generate waste that requires disposal. Some manufacturers develop a catalyst for a specific reaction however this may be time consuming. III. Starting materials availability: Availability of bulk chemicals that are cost effective must also be considered IV. Environmental factors: Safe containment of solvents reagents and waste disposal must also be considered. V. Number of steps: A synthetic route which requires fewer steps results in lower utilization time of equipment …show more content…
Ibuprofen: Part B. Figure 1. Structural features of Ibuprofen Ibuprofen has two functional groups; Carboxyl group (COOH) and an aromatic group (Benzene ring) the chemical formula for ibuprofen is C13H18O2. Part C. Ibuprofen consists of covalently-bonded carbon, hydrogen, and oxygen atoms. Two CH3 molecules are single-bonded to a CH molecule. The CH molecule is bonded to a carbon atom that forms a 6-sided ring of carbon atoms. Another CH molecule is single-bonded to a carbon atom on the other side of the ring. There are 3 double bonds inside the rings between carbon atoms. On the right, another CH3 molecule and a COOH molecule are both single bonded to the CH molecule. The following is the synthetic chemistry routes for synthesizing Ibuprofen. Step 1: Isobutyl benzene is combined with propionyl chloride through Friedel-Crafts acylation to form 1-(4-Isobutyl-phenyl)-propan-1-one. Step 2: 1-(4-Isobutyl-phenyl)-propan-1-one is converted to methyl ibuprofen through treatment with iodine and trimethyl orthoformate via aryl migration. Step 3: Methyl ibuprofen is hydrolyzed to ibuprofen by potassium …show more content…
Step 2: Diethyl 2, 4-dichloro-5-fluorobenzoylmalonate is partially hydrolyzed and decarboxylated with tosylic acid to yield ethyl 2, 4-dichoro–5 fluorobenzoylacetate (17). Step 3: Ethyl 2, 4-dichoro–5 fluorobenzene undergoes condensation (Dieckman like) with ethyl orthoformate which is carried out in refluxing acetic anhydride and results in ethyl 2(2-4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate. (18). Step 4: This is treated with cyclopropyl amine in ethanol to give ethyl 2-(2, 4-dichloro-5-fluoronenzoyl)-3-cyclopropylaminoacrylate.This results in removal (Michael addition) of the ethoxy group resulting in the enamine (19). Step 5: An intramolecular SNAr reaction of the enamine takes place resulting in a cyclised quinolone (20). This is formed in basic conditions using a base such as NaH or KH. Step 6: The ethyl ester on (20) is hydrolysed using concentrated sulphuric acid in a refluxing 1:1 acetic acid/water mixture. Step 7: SNAr displacement takes place of 6-fluro-7-chloroquinlone (21) with piperzine to yield
Reacting 1-butanol produced 2-trans-butene as the major product. 1-butanol produces three different products instead of the predicted one because of carbocation rearrangement. Because of the presence of a strong acid this reaction will undergo E1 Saytzeff, which produces the more substituted
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
The IR spectrum that was obtained of the white crystals showed several functional groups present in the molecule. The spectrum shows weak sharp peak at 2865 to 2964 cm-1, which is often associated with C-H, sp3 hybridised, stretching in the molecule, peaks in this region often represent a methyl group or CH2 groups. There are also peaks at 1369 cm-1, which is associated with CH3 stretching. There is also C=O stretching at 1767 cm-1, which is a strong peak due to the large dipole created via the large difference in electronegativity of the carbon and the oxygen atom. An anhydride C-O resonates between 1000 and 1300 cm-1 it is a at least two bands. The peak is present in the 13C NMR at 1269 and 1299 cm-1 it is of medium intensity.
A weak peak was at a position between 1600-1620 cm-1 can also be seem in the IR, which was likely to be aromatic C=C functional group that was from two benzene rings attached to alkynes. On the other hand, the IR spectrum of the experimental diphenylacetylene resulted in 4 peaks. The first peak was strong and broad at the position of 3359.26 cm-1, which was most likely to be OH bond. The OH bond appeared in the spectrum because of the residue left from ethanol that was used to clean the product at the end of recrystallization process. It might also be from the water that was trapped in the crystal since the solution was put in ice bath during the recrystallization process. The second peak was weak, but sharp. It was at the position of 3062.93 cm-1, which indicated that C-H (sp2) was presence in the compound. The group was likely from the C-H bonds in the benzene ring attached to the alkyne. The remaining peaks were weak and at positions of 1637.48 and 1599.15 cm-1, respectively. This showed that the compound had aromatic C=C function groups, which was from the benzene rings. Overall, by looking at the functional groups presented in the compound, one can assume that the compound consisted of diphenylacetelene and ethanol or
A condenser and heat reflux was used to prevent reagents from escaping. Then the solid product was vacuum filtered. The product was recrystallized to purify it and the unknown
In the 100 years after aspirin’s birth, although people appreciate its function of pain-curing, no one knew how aspirin actually works until the late 1990s. In the 1970s scientists learned that it is the release of prostaglandins, the molecules which are similar to hormone, after injuries that cause fever and inflammation. The analysis of PGHS (prostaglandin H2 synthase), the enzyme that produces prostaglandin finally reveals the working process of aspirin. The enzyme is surrounded by 2 protein subunit, arachidonic acid, a basic component of prostaglandin, travels through the channel in between the two protein subunits to the core of the PGHS enzyme. Aspirin molecule splits into two, saliucylic acid and acetytl group, after entering the channel of the PGHS enzyme. With the acetyl group blocking the entrance of the channel, arachidonic acid cannot get access to the core of the PGHS enzyme, hence stop the production of prostaglandin.
The reactions from the synthesis of lidocaine were reduction, acylation, and nucleophilic substitution. At the end of the experiment only one product was formed. However, each step in the synthesis of lidocaine created a product that was utilized in the next step of the reaction. If one step was missed or had an error that was not caught and corrected the entire synthesis process would have been thrown off. The ending product and the product that was expected was a purified form of lidocaine.
In this lab 2-methyl-butyn-2-ol is hydrated to 3-hydroxy-3-methyl-2-butanone. This process was preformed by using a strong acid which created an enol, and then the enol tautomerized. Due to this being a terminal alkyne, only one product will be formed. Techniques such as simple distillation, reflux, and gravity filtration were used to produce and separate the product from the mixture that it was in. When performing this lab using only one equivalent of alkyne produced a low percent of 1%. The low yield is a result of using one equivalent instead of two.
Background Information Aspirin is an analgesic (pain relieving) and an antipyretic drug (a drug that lowers body temperature). The main constituent of aspirin is 2 - ethanoythydroxybenzoic acid, also known as acetylsalicyclic acid (shown below right). It was originally made from just salicylic acid (which is found in the bark of a willow tree) when used by the Ancient Greeks to counter fever and pain, but its bitterness and tendency to irritate the stomach caused problems. These were resolved by the German chemist Felix Hoffman, who made the acetyl derivative of salicylic acid in the
The components of an analgesic will be determined by noting the separation between the solid and liquid (or mobile) phases and comparing it to these predicted reference values.
The only anti-inflammatory drug for over a half a century was Aspirin. Unfortunately, Aspirin causes many side effects when taken in large doses such as ulcers and bleeding in the intestines. Experts knew they had to discover another remedy to help pain sufferers. A medicine alternative called Paracetamol was discovered, but did nothing to take away pain. In 1948, Cortisone was discovered. It was considered a miracle until side effects developed from the drug. In 1980, Ibuprofen went over the counter and has become the most well-known anti-inflammatory. Pain relief has come along way through the years. It has not always been as easy as it is now to get rid of pain. Many people had to suffer because of having no solid pain relieving methods.
The production of synthetic detergents are an example of a standard chemical approach. If a useful substance has some undesirable properties an attempt is made to make a near copy synthetically which will perform better.
The article selected was released by Phys.org, a scientific research organization. It describes the success of chemist Phil Baran and his team in discovering an authentic technique to modify complex drug molecules. The following passage has been extracted for further analysis:
It is important to have clean and long-lasting environment because today the world faces increasing environmental issues, such as pollution. This cannot happen only by decreasing the amount of people's waste or using less energy. Thinking deeply about developing protection processes is also important as well as realizing how these issues affect people's life in present and future. Therefore, chemical engineers take environmental problems into account to decrease pollution. Rattan (2014) explained that beside other problems, saving environment, controlling toxic materials pushes chemical engineers to take into consideration any areas related to modern ecological safety in community. To illustrate, today chemical engineers oversee and improve safe production processes through controlling pathways of reaction and see if it produces pollution or not. Moreover, reducing, treating and safely disposing unused products is another way chemical engineering has contributed to protecting the
2). The cycle is broken into eight consecutive stages (Table 1). The first step initiating the cycle involves acetyl CoA reacting with oxaloacetate to first produce citryl CoA and then citrate from further hydrolysis. In the second step, citrate is isomerised into isocitrate. This is achieved through a dehydration and hydration step with cis-Aconistase produced as an intermediate and the aconitase catalysing the overall reaction. The third step involves isocitrate undergoing decarboxylation and oxidation reactions to form alpha-ketoglutarate (Berg J.M et al., 2015). In step four, a second decarboxylation oxidation reaction occurs to form succinyl CoA from alpha-ketoglutarate. Step five involves splitting succinyl CoA to produce succinate and CoA. In step six, succinate is oxidised to fumurate and FADH2 is formed simultaneously (Ness B., 2017). The penultimate step involves fumurate being converted to malate. In the affixing step of the citric acid cycle, malate is oxidised to form oxaloacetate, enabling a cycle to be established (Berg J.M et al., 2015).