Nitration of Acetanilide and Methyl Benzoate

Nitration of Acetanilide and Methyl Benzoate Nitration of Acetanilide and Methyl Benzoate by Electrophilic Aromatic Substitution Abstract The purpose of this experiment was to synthesize methyl nitro benzoate from methyl benzoate, as well as nitroacetanilide from concentrated nitric acid (HNO3), and concentrated sulfuric acid (H2SO4) by using an electrophilic aromatic substitution reaction. The HNO3 and H2SO4 were combined to form a nitrating solution, which was added to a mixture of methyl benzoate and H2SO4, and the same was done with acetanilide. Following recrystallization, melting point was used to identify and characterize the product of the reaction. The melting point was determined to be 74 ËÅ ¡C-80 ËÅ ¡C for methyl nitro benzoate and for nitroacetanilide it was 195 ËÅ ¡C-200 ËÅ ¡C, which indicates meta-regiochemistry for methyl benzoate and para-regiochemistry for nitroacetanilide. The percent yield of this reaction for the recrystallized product was 59.3% of methyl nitrobenzoate, while it was 6.75% for nitroacetanilide. Figure 1: The reaction for the nitration of acetanilide. Figure 2: The reaction for the nitration of methyl benzoate. Experimental Concentrated sulfuric acid (0.6 mL) and concentrated nitric acid (0.5 mL) were added to a reaction flask and placed in an ice bath. Concentrated sulfuric acid (1 mL) was added to methyl benzoate (0.5 g) in a vial which was then packed in ice, and the same was done with acetanilide.ÂÂ   While stirring, the cold H2SO4/HNO3 mixture was added drop-by-drop. After the acid mixture was added, the reaction mixture was removed from the ice to warm to room temperature, with stirring. It was then transferred by Pasteur pipet into a beaker and stirred for five minutes. The methyl benzoate nitration formed white solid, and the acetanilide nitration for a light yellow solid. The crystals were the vacuum filtered with a Buchner funnel. The crude product was recrystallized by adding a distilled water and ethanol slowly while heating the product. While cooling, the solution produced large white crystals for methyl benzoate nitration and light yellow crystals for the acetanilide nitration. The ma ss, melting point percent yield were obtained. Results and Discussion Through the use of electrophilic aromatic substitution, acetanilide is nitrated to nitroacetanilide, while methyl benzoate was nitrated to methyl nitrobezonate. The first step of the reaction involved in the donation of an electron pair, which generates the nitronium ion from nitric acid by protonation and loss of water, using sulphuric acid as the dehydrating agent. The mechanism for methyl benzoate can be seen below. Figure 3: The mechanism of the nitration of methyl benzoate to methyl nitrobenzoate. To prevent acetanilide from dinitrating, the nitrating solution of HNO3 and H2SO4 were added drop by drop to the acetanilide solution, so that the concentration of the nitrating agent is kept at minimum. The cooler temperatures were used to reduce the reaction rate and help to avoid over nitration. The electrophilic aromatic substitutions involved the replacement of a proton on an aromatic ring with an electrophile that becomes substituent. The sulfuric acid protonates the methyl benzoate, which creates the resonance stabilized arenium ion intermediate.3 The electron deficient nitronium ion reacts with the protonated intermediate meta position. The ester group is the meta deactivator and the reaction takes place at the meta position because the ortho and para positions are destabilized by adjacent positives charges on the resonance structure.2 The major product of the methyl benzoate nitration is the meta product due to carboxyl and nitro groups both being powerful electron withdrawing groups. Table 1: The weight, melting point, and percent yield of both Nitroactenilide and Methyl Nitrobenzoate. Product Name Crude Weight (g) Product Weight (g) Percent Yield (%) Melting Point (ËÅ ¡C) Literature Melting Point (ËÅ ¡C) Nitroactenilide 0.585 0.045 6.75% 195-200 214-217 Methyl Nitrobenzoate 0.56 0.32 59.3% 74-80 78-80 The actual yield of methyl nitrobenzoate is 0.32 g while the theoretical yield is 0.54 g. The melting point is 74ËÅ ¡C 80ËÅ ¡C, and the value is closed to the literature value which is 78ËÅ ¡C 80 ËÅ ¡C. The percent yield for the methyl benzoate electrophilic aromatic substitution reaction was 59.3% with 0.32g of methyl nitrobenzoate formed. The percent yield for the reaction with acetanilide was 6.75% with 0.045g of nitroacetanilide formed, which can be seen in table 1. The melting point observed was 195-200 ËÅ ¡C, which can be accounted for impurities in the product, which can be seen below in table 1. Some impurities might be Ortho and Meta directing substances, as well as there could have been some experimental errors that occurred during the experiment such as not overheating solutions during the reactions. These low yields may have resulted from poor recrystallization, product lost during transfer from one apparatus to another, or human error. The miss ing percent accounts for the impurities removed during recrystallization. However, some product must have been lost in the acetanilide reaction recrystallization because of such a low percent yield. The melting point of the final product was 74-80 ËÅ ¡C suggesting that it was formed by meta-substitution. The literature melting point for meta-methyl nitrobenzoate is 78-80 ËÅ ¡C. Therefore, the melting point is lower than it should be suggesting that an impurity is in the product. This impurity may have occurred due to poor recrystallization or it may have been picked up after recrystallization. The melting point of the nitroacetanilide product was 195-200 ËÅ ¡C suggesting the para-regiochemistry. The literature melting point for the p-nitroacetanilide is 214-217 ËÅ ¡C. Therefore, the melting point of the product is a little lower than the literature value, suggesting that an impurity exists in the product from poor recrystallization of contact with an impurity during recrystallization. The methyl nitrobenzoate product was determined to be meta-substituted based on its melting point range. This can also be proved by evaluating the attack of the benzene ring of methyl benzoate on the electrophililic species and nitric acid.4 The C-OCH3 substituent is a meta-deactivator. Therefore, when the benzene ring attacks the nitronium ion, the NO3+ group will add meta-positon. This creates a resonance stabilized arenium ion without a positive charge on the carbon with the C-OCH3 substituent. Then the proton is removed from the meta position by the weak base, the HSO4-, formed in the creation of the nitronium ion, which reforms the sulfuric acid catalyst.3 Once the proton is removed the substitution product, methyl nitrobenzoate remains. The nitroacetanilide product was formed by a para-substitution. This can be determined by examining the melting point and comparing it to the literature values for each position.4 However, this can also be determined when examining the electrophilic aromatic substitution reaction of acetanilide on the electrophile, nitric acid. The NHCOCH3 substituent is an ortho-para-activator. Therefore, when the benzene ring of acetanilide attacks the nitronium ion, it can add ortho or para. The para substitution, if more stable than an ortho substitution, will be added because the para position is a further distance from the position of the NHCOCH3 substituent. Therefore, the benzene ring adds at the para position based on the melting point and resonance in the mechanism shown above. Conclusion The methyl m-nitrobenzoate and p-nitroacetanilide were prepared. The percentage yield is 6.75% for nitroacetanilide and 59.3% for methyl nitrobenzoate. The melting point of the products are 74ËÅ ¡C 80ËÅ ¡C and 195ËÅ ¡C 200ËÅ ¡C. From the given physical constant, the literature melting point of methyl m-nitrobenzoate is 78 80ËÅ ¡C and 214ËÅ ¡C 217ËÅ ¡C for nitroacetailide, so it can be concluded that the products were methyl m-nitrobenzoate and p-nitroacetanilide. References Wade, Jr., L.G. Organic Chemistry 2003, 722-741. Chemistry Laboratory Manual: Susquehanna University 2014, 242-244 250 ChemFinder.Com. Cambridge Soft Corporation. . Anerjee, Dhruv K. Ortho and Par % of Key Reaction. Utkarschemistry. 2013. Appendix A: Finding the Limiting Reagent Grams X 1 mol / molecular weight = moles of reactant Nitric Acid: 0.6 mL X ((1 g/1 mL) X 1 mol) / 98.08 g/mol = 0.0061 mol Nitric Acid: 0.5 mL X ((1 g/1 mL) X 1 mol) / 63.01 g/mol = 0.0079 mol Methyl Benzoate: (0.55 g X 1 mol) / 181.14 g/mol = 0.030 mol Appendix B: Calculating Theoretical Yield of Methyl Nitrobenzoate Moles of limiting reagent X molar ratio X molecular weight of product) / 1 mol = theoretical yield (0.030 X 181.13) / 1 mol = 0.54 g Appendix C: Calculating Percent Yield (Actual / theoretical) X 100% = percent yield (0.32 g/ 0.54 g) X 100% = 59.3%

Cross Cultural Communication- Royal Dutch Shell’s Approach Essay

Shell has over 100 different nationalities in its employee population. In a global organization like Shell, people need to constantly work with people from other nationalities as part of expatriate assignments. We had a candid interaction with company’s global learning head Manojit Sen. We are elucidating few interesting points from the discussion. Global organisations like Royal Dutch Shell face the constant challenge of cross cultural communication both when dealing with external customer as well as in dealing with colleagues internally. Some of these are: Failure to Bond: Experience over years shows that customers like doing business who are like them. Equally Sales staff unconsciously look to do business with people they like and stay away from those they don’t like and bond with. The more pronounced the differences between two people, the slower the bonding process may be, especially if nothing is done to bridge the gap such as teaching people to communicate like à ¢â‚¬Ëœone of them’. Hence the fate of multi billion dollar deals in oil majors such as Shell may often be tested on the strength of the ‘liking’ factor. Stereotyping: Even with the best education, almost everyone consciously or unconsciously holds onto some unfair generalizations about a given group. Recognizing and overcoming negative beliefs that we may have had since childhood can be challenging. These generalizations come in the way of truly listening to views and building on the best of ideas which have the potential to take the organization forward. Assuming the same values: We all assume everyone shares the same values we do. This leads to judgments of what is right and wrong, acceptable and unacceptable. When the values are not actually the same, actions one party takes does not meet the expectations of the other leading to frustration, attribution of intent and breakdown of trust. â€Å"Token† syndrome: In big multinationals where consciously the numbers of different minority groups have been increased over the years, people from underrepresented groups may sometimes feel that they are in the spotlight due to their low numbers. Since their difference tends to make them stand out, they may believe that they receive unfair scrutiny. As a result, they may fear making mistakes or being perceived as receiving special treatment. â€Å"Protective Hesitation†: The cultural differences between a staff and his customer or colleagues from another  culture may lead both parties to view their relationship as less solid than other relationships with people from the same culture. To overcome this, people may tend to overcompensate and then fear that the response may appear to be ‘too cosy’ and subject to criticism. Making mistakes: Whether or not staff have had a lot of experience working with people from the customer’s or colleague demographic if it from a different culture, he may inadvertently say or do something that the customer or colleague finds offensive. It’s a lot easier to get past mistakes if both parties believe that the two have the same values and mindset. Cases where these type of issues have resulted in problems and ways in which these were handled include: 1. A Dutch project manager used to straight talking posted in UK’s North Sea Joint Venture upstream project upset the staff by telling them off on a few occasions to the point that the JV agreement was getting close to being called off. The Dutch manager had to be replaced despite his strong technical credentials and subsequent appointees were put through cultural awareness training before being sent off to this and similar JVs. 2. An Australian posted in India’s new retail operations to set up the Health, Safety, Security and Environment department was so frustrated by vendors promising to do everything and not meeting quality and timeline issues that he started to call them ‘liars’ on the face, alienating himself from the few vendors who were able to meet the quality specs of Shell. This disrespectful behavior and loss of face resulted in vendors refusing to work for Shell and consequent delays in commissioning of retail stations by over a couple of months, a stalemate that had to be broken by skillful negotiations by local managers. 3. In a virtual cross country project team working on implementation of a Retail network project months in China that had to deliver its implementation plan within 3 months, would have its team meeting every week. From the start the Chinese staff on the team were quiet. The Americans spoke the most. They believed they were contributing and the Chinese were not. It emerged after 8 weeks when a milestone was missed that the Chinese could not understand a lot of what the Americans were saying, let alone their jokes. The team lead was prompt to realize this  was a sign of impending disaster and promptly made official rules on talking time at each meeting so that everyone had his time, including time to ask clarifications and to recap what each understood. 4. A Danish IT staff was on a global SAP implementation project. Since she was reporting to a Singaporean manager, she would have to take calls early her morning. Sometimes she would have to join calls with US colleagues working on implementation issues. With work life balance being a very important aspect of the Nordic culture, she was direct about how she felt on a number of occasions. The manager had given her the flexibility to take time off during the day to make up for this but somehow this did not help and the Danish lady started missing calls and issues did not get addressed in time. She also did not check emails or even phone messages during the weekends. Issues started to get escalated and reached the point where the vendors implementing the ERP charged Shell for delayed decisions leading to having to rework project plans and consequent costs and delays. This became a performance issue that required the staff to be replaced by someone who was much more flexible – something that was needed during this critical stretch period. 5. The Shell team negotiating a significant gas deal in Middle East included only Europeans. The local Middle East team felt more comfortable with the American- Saudi Aramco team as it had more Middle Easteners. This was recognized in time and Shell’s team was revamped to include a few ‘local’ faces who could help break the ice and guage the local sentiments. With issues such as these multinational organisations need to work on many cross cultural issues which impact communication internally and externally. The are typically managed via the Diversity and Inclusion agenda. In Shell, the D&I agenda includes:   D&I education offerings.   Communication processes in the profiling of success stories and the sharing of good practices. Recruitment and retention efforts that focus on tapping into the top talent across diverse constituency groups. Development and mentoring of diverse staff from across the world. Building supportive/inclusive work environments. D&I  education: Shell has over 100 different nationalities in its employee population. In a global organization like Shell, people need to constantly work with people from other nationalities as part of expatriate assignments, or as part of x-country projects or as part of one’s role which may be global or regional in scope. Hence educating staff on nationality related cross cultural issues is an ongoing activity in Shell. Staff who get posted as expatriates to a foreign country are taken through cultural awareness sessions on the new country culture. They are also sponsored to learn the local language to help assimilate better. Staff put on x-country assignments are also helped with cultural awareness sessions so that they can understand what colleagues from other countries mean by what they say and by what they don’t. Supervisors who have from different countries are also encouraged to understand the cultural differences of countries of these staff. The Crossing Cultures course in Shell is designed to help people value differences and improve team working skills. The course aims to enable business and function staff to develop their cross cultural skills and to work more effectively, with virtual and multi cultural teams. Participants are expected to: Improve their sensitivity to others’ different needs and behaviours and adjusts own behaviours and communication style accordingly. Invites, respects and incorporates others’ different perspectives. Demonstrates a non-judgemental acceptance of different perspectives, behaviours and ways of working. Utilises cultural differences to improve outcomes. Actively supports efforts to build a more diverse and inclusive organisation. This course consists of a structured program of face-to-face and virtual learning, combined with workplace assignments and activities, knowledge sharing and networking. The course totals 16 hours; 8 hours virtual over 4 weeks and with a 1 day face to face in week 6 of the program.

The Creation of the American Democracy Essay - 872 Words

The Creation of the American Democracy When the Framers of the Constitution met in Philadelphia, they came together with one common purpose in mind. They needed to form a fair and solid system of government that would stand the test of time; one that was both fair for the people and would not involve a monarchy. Each of these men had their own ideas on what would constitute this system, however, so many compromises had to be made. Together, the men gathered in Philadelphia created a federal system of government and drafted a constitution outlining this government. They took care in developing three branches of federal government with a system of checks and balances so that no one branch would gain too much power, thus avoiding any†¦show more content†¦While the popular party was in favor of using paper money to pay off debts, such as was done in Rhode Island, the upper-class patricians saw this as unacceptable. Since the Philadelphia Convention consisted of the conservative aristocrats (there was no represen tative from Rhode Island), paper money was outlawed and a national bank was set up. Although this may have been the fairest and most logical set-up, it was not a democratic plan because it did not uphold the common interests of the people. The Electoral College is also an example of a plan implemented by the Framers that does not always uphold the common interests of the people. While many reasons are cited as to why the Framers chose this system, two stand out as being most prominent: They were concerned about representation for small states, and they wanted a precautionary system to ensure that the official who took the oath of President was indeed able to sufficiently perform these duties. Electors were supposed to vote with the majority decision of their state, but there was no law saying they had to. 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Summary of What Happened in Each Chapter of the Novel The Catcher in the Rye

Summary of What Happened in Each Chapter of the Novel The Catcher in the Rye The Catcher in the Rye Chapters Holden Caulfield retells the story of his childhood from a rest home as an old man. As a young teen, he is suspended from Pencey Prep school. He goes to his elderly teacher Mr. Spencers house, where he is greeted. Holden talks to Mr. Spencer, who reminds him that he flunked him from his history classes, and reminds him that life is a game that you have to play the rules to in order to succeed. Holden is pestered by Ackley, an irritating student who disgusts Holden with his poor hygiene. Ackley does not leave until Stradlater, Holdens roommate, shows up. Holden notes that Stradlater is clean-cut and still a secret slob, while Ackley is more openly so. Holden gets jealous of Stradlater taking Jane Gallagher out on a date. Holden starts a snowball fight; later, he starts a paper Stradlater asked him to write for him. He writes about a baseball glove that reminds him of an old friend Allie, who died years ago, but whom Holden still misses. Stradlater comes back from his date with Jane, and gets into a fight with Holden rather than tell him about how the date went; Holden is clearly jealous and angry that Stradlater is dating Jane. Still stewing about Jane and Stradlater, Holden decides to pack up and leave for New York right away. He gets packed up and yells out Sleep tight, ya morons! before finally leaving Pencey for good. At the train station, Holden surprisingly meets up with the mother of another classmate. Despite the fact that he does not like him, he lies to her and tells her positive things about him, lying about his own name. Once he arrives at Penn Station, he chooses not to call anyone, and instead goes to the Edmont Hotel. Turned on by the things he sees on the cab ride there, he tries to call Faith Cavendish in order to get laid, but she refuses to meet him right then. At the Edmont, he goes down to the Lavender Room and tries to buy a drink; however, he cannot manage to do so. He attempts to flirt with three older women, but they are unimpressed by him. He gets dejected and leaves after buying them drinks. Holden thinks about Jane and his history with her. Since living next door to each other as children, he has carried a torch for her, but her abusive stepfather traumatizes her and makes her sad. Holden goes to Ernies, a nightclub, and meets various people along the way, including the angry cab driver, and Lillian, a girl whom his brother DB used to date, leaving the nightclub. Going back to the Edmont, depressed, he reflects on his cowardice. He imagines telling off the person who stole his gloves back at Pencey; he then tries to make up for it by ordering a prostitute from the elevator operator. This is unsuccessful, as he is too flustered. Holden reminisces further about his childhood with Alice, but is interrupted with the doorman, who asks for the extra money he owed the prostitute. He is beaten and stolen from, and he only imagines standing up to the elevator operator. Holden has a date with Sally Hayes, which he sets for later that day. Eating breakfast, he talks to some nuns, whom he gives money to out of a sense of obligation, later regretting that he doesnt have that money for the date. Holden buys a record for Phoebe, and chooses to call Jane, but does not get through to her. He buys tickets to the theater for his date with Sally; he then reminisces about his old school trips. Holden goes on his date with Sally, and goes to the theater with her. After her flirting with other men, Holden gets angry, and eventually tells her off, making her cry. He leaves the date without her. After the date, Holden goes to Radio City Music Hall and is unimpressed by both the Rockettes stage show and the movie that plays there. At the Wicker Bar later, he thinks about the army and how he would not want to be there, meeting Luce. Holden thinks about his friend Luce, an older boy from school who was always very sexually preoccupied when they were younger, but then refused to talk about it. Luce suggests that Holden needs psychoanalysis. Holden gets drunk at the bar and calls Sally Hayes late at night, making her angry. He proceeds to flirt with other girls at the bar. He breaks the record he purchased for Phoebe in Central Park, and decides to head home. Going to his familys apartment, Holden sneaks in and finds Phoebe, waking her up. They catch up, but then clams up with him after realizing he should not be home. After getting Phoebe to continue talking to him, he explains the reason why school sucks and why he flunked out of his classes. Phoebe and Holden discuss the issue of their dead friend Allie, and Holden contemplates what he might want out of life. Holden calls his English teacher, Mr. Antolini, and discusses plans to meet him. Hanging out with Phoebe a bit more, he hides from his returning parents, and sneaks out of the apartment to move west on his own. Holden goes to Mr. Antolinis place, and talks to him about his expulsion from Pencey. Mr. Antolini calls him out on his overt cynicism and his tendency to digress. Antolini is worried about Holden because he is about to fall apart or hit bottom; Holden becomes defensive about that, but Antolini insists that he is not ready for the outside world. He tries to sleep at Antolinis place, but rushes out after believing that Antolini is making a pass at him. Holden goes to Grand Central Station to leave, but decides to meet Phoebe at the Museum of Art and say goodbye to her. Phoebe instead asks to go with him, but he refuses; they go to the zoo instead for one final good memory. Holden goes to the rest home after getting sick, from which he will go to another school in the fall; it is left ambiguous as to whether or not he will make changes in his life.