The impact of gender in research

The impact of gender in research Does the gender of the interviewer effect the response rate, interview and the results obtained? Many researchers have investigated the effect that interviewers gender has on research, this paper seeks to examine if there is an effect and how relevant that effect is. It will draw on academic papers, business examples and a case study. Hyman et al (1954) were one of the first to examine the effect gender-of-the interviewer has on the interview process; they found respondents replied differently to male and female researchers. Since then there has been an abundance of research in the field, much of the research is based on and argues that gender-of-interviewer effects are evident on, topics related specifically to feminism, politics and other sensitive issues. This paper will analyse the research and apply it to a case study. With the main aim to determine if the gender-of-interview affects all interview areas or whether it is topic specific. It is important to understand what is meant by interviewer effects; interviewer errors are expected to occur differently in every interview whereas interviewer effects refers to a specific interviewer characteristic i.e. gender (Dijkstra 1983). Interviewer effects look at how interviewer variance can bias the results of research. The case study being looked at took place in Oldham, it was a consultancy project investigating participation rates of food waste recycling, with the main objective to increase participation rates. The methodology used was semi-structured interviews and drop off questionnaires. The interviewers were made up of two women and three men. Researchers went out in pairs, for safety reasons, the researchers went out in four pairings, three pairs made up by a women and male interviewer and the final pairing was comprised of two male researchers. Due to time constraints and the nature of the work this case study was unable to talk to residents about their impression of interviewer-gender-effects. However all interviewers were interviewed extensively by the author of this paper, to grasp their view of the effect gender had. The main topics covered were response rates, lengths of interviews and results obtained. Does the gender-of-interviewer affect response rate? Gender can affect the response rate; Smith (1972) suggests that women are less likely to invite men interviewers into their home explaining that it is due to the perceived danger, this argues Smith can be an issue for male interviewers conducting research. When looking at the Oldham Case study this was evident, the response rate for the mixed paring had a higher response rate to the male only pairing. The mixed pairings had a response rate average of ? and the male only pairing had a response rate average of  ¼. This is backed up by Dommeyer (2008) whose study examined how using a photo in the cover letter of a drop off questionnaire effects responses. Female interviewers prove to obtain a higher response rate. His research found that rivalling the gender was only productive if they were female. Bean and Medewitz (1988) had similar results when sending out cover letters with a female signature; a higher response rate was produced than when a male signature was used 35% and 26% resp onse rate respectively. Moreover, Catonia et al (1996) experiments found that on a phone interview when respondents were given the opportunity to request a gender 82%, of women and 72% of male respondents did request with the majority selecting a female, suggesting that respondents prefer female interviewers. When interviewed, Keith from the Oldham case study expressed: Sandra seemed to get a higher response rate then I did, we quickly realised this and Sandra became the interviewer and I the scriber. Johnson and Delamater (1976) discuss, whilst looking at response rates in sex surveys, the effect gender has on respondents agreeing to be interviewed. They argue that the gender of the interviewer can have a substantial effect on response levels; attributing it to the type of survey suggesting that if they are embarrassed about the topic being discussed they may be less likely to opt to participate, especially with someone from the opposite gender. In the Oldham case study this can be compared to respondents who do not participate in recycling and are therefore are less likely to agree to be interviewed, however the gender of the interviewer is unlikely to make a difference there. Benny et al (1956) notes that male interviewers gain fewer responses to female interviewers and most of these are from female respondents. Rourke and Lakner (1989) discuss the gender bias that exists within the data collection.. How does gender affect the results obtained? Huddy et al (1997) looked at the effect that the gender-of-interviewer had in two surveys, where male and female interviewers were randomly assigned to interview male and female respondents. With the first survey; gender of interviewer had more of an effect on less educated and younger respondents. However these results were not replicated in the second survey. Yang and Yu (2008) argues that well educated people are not affected by gender as much because they are more use to inter-gender relations. Huddy et al (1997) also attribute it to the fact that people that are more educated are more confident in the company of the other gender. WHAT IS EDUCATION IN OLDHAM? Many researchers have suggested that the gender of the interviewer only has an effect on certain topics. Huddy et al (1997) suggests that the gender-of-interviewer is more predominant when; politics and views on feminism are discussed. Bellou and Del Boca (1980) found stronger gender-of-interviewer effects among women respondents on questions about the existence of gender inequality whereas men tend to be more affected when questions about women movements arose. Flores-Macias and Lawson (2006) claim that in the past research has shown effect on social and political issues when interviewed by different gender. Using a survey on households in Mexico the research tries to add to the field, they found gender effects were confined to sensitive questions, they concluded gender-interviewer effects are limited to gender topics. TOPIC OF RECYCLING In contrast Kane and Macauley (1983) note the opposite; Women were most effected by questions on womens movements for example collective action and women shared interest, while men were more effected by the interviewers gender when answering work-related gender equalities. Gender bias was highest with questions related to controversial politics and womens movements. Kane and Macaulay (1993) research looks at the effects of interviewer gender on responses in particular on gender-related survey questions. They look at if gender effects are present and how it differs from male and female. Huddy et al (1997) argue respondents are susceptible to gender-of-interviewer effects across a broad spectrum of gender-linked items. Groves and Fultz (1983) found that economic indicators receive more optimistic responses when interviewed by a male interviewer rather than a female interviewer. Landis et al (1973) reported that when women were interviewed by male interviewers they gave more feminist responses on womens roles. Kane and Macaulay (1993) summarise stating after analysing gender-attitude it is clear that interviewer-gender bias is present, it tends to include respondents giving a critical response to female interviewers than to male. On standard debate topics men are more likely to be effected by the gender of the interviewer and are less likely on less familiar topics. Womens responses vary dramatically in their responses to male and female interviewers on various issues. They did not see a vast difference in interviewer gender effects for example respondents to male respondents. It is therefore questionable on it social power effects conversational power in the interview process. Both male and female respondents are at times affected by interviewer gender. In contrast Herod (1993), who is a geographer, believes that the gender-of-interviewer can effect responses on any topic discussed. He argues that gender relations are an important aspect that can shape the interview process, gender can shape the type of data collected especially when carrying out interviews. Backing this up is McDowell (1992) who explains how interviews raise the issue of gender, Schaenberger (1992) agrees gender makes a difference (p.217). In the Oldham case study gender.. look at results! Herod (1993) gender can shape the use of interviews as a research tool (p.306). Even when all respondents are of the same gender, gender bias still shapes the interactions between interviewer and interviewee. Feminists support this statement gender is significant in society it is always going to effect gender relations in the research process (Keller 1985). Herods paper looks at work conducted across different disciplines on gender and its effect on interviewing. Turner and Martin (1984) in the classic work discuss how the gender-of-interviewer and the respondent has significant effect, the different options (male interviewer, female respondent/ male interviewer male respondent etc) have different effects in influencing opinions and feelings. Eagly and Carli (1981) showed a statistical relationship between the gender of the interviewer and outcome of the interviews showing both; respondents giving different answers to male and female researchers, but also researchers interpreting it differently. Thus this demonstrates that an interviewers gender can affect respondents answers. Looking at the Oldham case this can be demonstrated through interpretation of answers, when looking at how the answers were interpreted it is completely a subjective task, when a male was interrupting it, the results appeard whereas when a female was interrupting it is seemed. Even when it is the same gender there is an effect, Aries (1976) suggested that men tend to be more aggressive and macho to a male interviewer. Herod (1993) explains whereas a male interviewer may display one type of behaviour with female researcher he may show a different one to a male therefore obtaining different results. Oldham case study.. Piliavan and Martin (1978) found that in a group setting men and women acted differently, in the Oldham council case study, researchers went out in pairs often a man and women researcher, Aries (1976) explains that she observed women were less likely to interact than men in a mixed group. This could have affected female respondents answers when being interviewed by a male and female researcher in the Oldham case study. Moreover Herod (1993) notes the difference in the way male and female genders interpret information, on an interview he refers to the type of language used. Carli (1991) claims that women and men use language differently. Lakoff (1975) argues that women have to be socialised to use language that is less assertive then men and womens expressions are tentative. Herod (1993) puts forward that these stereotypes have implications when men and women interpret language. Sociolinguist, Deborah Tanen (1990) claims that men and women have different beliefs of how conversations are meant to work, as well as different views on the role of conversational interaction and building relationships (Wolfram Schilling-Estes, 1998). Herod (1993) explains that there is a danger in trying to generalise about gender relations in such broad categories. Arguing that they themselves did not look at race or class and how these shape gender. There is a need to look at how gender can mean different things in different context. Interviewing is about how interviewers generate meanings and understandings. Are men or women more affected by gender-of-interviewer? Whelcher (1987) and Ballou and Del Boca (1980) both argue that male respondents show more effect from gender-of-interviewer. Whelcher (1987) documents that men give more democratic responses to male interviewers as they try to give the response that they feel the male interviewer wants to hear. Ballou and Del Boca (1980) states how men give more democratic responses to female interviewers. Landis et al (1973) explain that it is expected that during an interview relationships are formed between respondent and interviewer and thus the behaviour of the respondent is influenced by their perception of the circumstances. Warren (1988) argues that women are better at building a rapport when interviewing. Landis et al (1973) found from their results that the women interviewed gave a more feminist response to the male interviewer, noting that the statistics were significant. They summarise that the gender of the interviewer does have a marked effect on response to women. Hyman et al (1954) found that gender of interviewer effected female respondents results when a male asked the question; 61% agreed with the statement, but when they were interviewed by women only 49% agreed. Hyman concluded women felt more obliged to give conventional opinions to a male interviewer. Benny et al (1956) note that both men and women act differently in the company of the other gender; acting more formally and expressing less. Benny et al (1956) and Hyman (1954) both argue that women in the presence of men talk more traditionally are more formal and tend to give the expected answer. Oldham Case study then this >It could be argued that as both these papers are dated, the findings may be less relevant. Macaulay (1993) claim the more egalitarian answers are more persuasive among male respondents when interviewed by a women. Flores-Macias and Lawson (2006) found that men are more likely to be effected rather than women. Furthermore that the social context has an effect, culture for example in Mexico City men were more susceptible to gender bias backing this up. Approximately 30% of men interviewed by men felt women rights were urgent however 40% interviewed by women felt it an issue. They also found women were more progressive when interviewed by men. Holbrook et al (2003) argue that effect from respondents believe they try to answer what interviewers want. Oldham Case study Davis et al (2010) argue that interviewer effects can impact the data obtained. They looked at measuring and controlling interviewer effects. Effects can occur from interviewer related issues such as the way questions are read, probes are used, instructions to survey etc (OLDHAM CASE study difference between male and female). Davis et al (2010) discuss how gender is the most noticeable characteristic of an interview and therefore is most susceptible to having an effect. In the past women were considered better interviewers because they are seen as less threatening and therefore there has not been as much research on this topic. But since telephone interviews gender has become more of an issue as no longer can the respondent see socioeconomic status, physical attractiveness, personal demeanour (Huddy et al 1997, p.197). Huddy et al (1997) note that there is growing evidence that respondents are more likely to give a feminist view to a female interviewer as the respondent seeks to give the answer they think the interviewer wants to hear. OLDHAM CASE Huddy et al (1997) had two goals from their study to test for the existence of gender-of-interviewer effects across a range of gender related questions. And to explore the characteristics of respondents most liable to gender-of-interviewer. Huddy et al (1997) wanted to test to see if the existence of gender-of-interviewer effected a range of topics or just gender related questions to achieve this they used two surveys both containing questions that dealt with womens issues and womens movements. Their results showed respondents were more likely to give a feminist view to a female interviewer on 11/13 gender related topics. However the difference obtained by male and female interviewers was small and consistent and was only significant for a minority of questions. The topics that showed gender-of-interviewer effects differed from the two surveys in the first, carried out in 1991 the largest gender-of-interview effects occurred on questions relating to feminist identity whereas in the second, obtained in 1993 they were on topics on abortion and anti-sexual harassment legislation. In both surveys a female interviewer collected more feminist views then a man. They did find, however that gender bias occurred most on both surv eys when topics on controversial politics were broached. With Huddy et al (1997) second goal they discovered significant interaction between interviewer gender and education less-well educated respondents were more influenced then well educated by the interviewers gender. Despite this the same results were not emulated in the second survey but they argue this could be because the gender bias was not as affluent either. To reinforce this Huddy et al (1997) assessed the statics of education and effect of gender on respondents with 12 and 17 years of education. They found that gender-of-interviewer effects were more prevalent with less educated respondents. Overall respondents with less formal education were more likely to be effected by the gender-of-interviewer and on gender related questions. Huddy et al (1997) note that gender bias decreases with age and income was the only demographic characteristic that did not increase. But how important is it, does it have a large enough effect to matter? Huddy et al (1997) found that small differences in their study. They conclude that it depends on the survey being administered. If it will effect then it is crucial that an equal number of men and women are randomly assigned to respondents. Finally Huddy et al (1997) believe that from their results it can be seen that gender could effect any type of survey and use the beginning of their first survey to demonstrate this point; where gender bias is present and the topic of the survey has not been disclosed. Huddy et al (1997) argue the view gender-of-interview effects questions is premature because; rarely have researcher controlled the individualism of interviews when examining gender-of-interviewer effects, few studies have measured the size of effects across a broad spectrum of questions to see if the effect is on feminist questions or all topics. Bellou and Del Boca (1980) did look into this in their 1980 study. Huddy et al (1997) continue explaining that effects are not standard even for questions on the same topic and few studies have tested the statistical significance across several variables with the same respondent. Huddy et al (1997) suggest that not enough research on which gender is most prone to gender-interviewer-bias as there is a contrast in theories. Lueptow, Moser and Pendleton (1990) argue women are more likely to give feminist views to a female interviewer, which they proved through telephone interviews. In contrast Ballou and Del Boca (1980) contrasted stating male respondents are more vulnerable to female interviews and appear more feminine. McDowell (1988) disagrees arguing that there is no gender split in research methods but rather a stereotyping in gender characteristics. Little work has been done on the effect of the interviewers gender; as traditionally interviewing was a female occupation Williams (1964) in his classic paper hypothesised that the greater the amount of social difference between interviewer and respondent the more likely of gender bias. Demonstrates the importance of the gender of interviewer and that the subject can have an effect.

A Turkish Student and the Board of Regents :: Argumentative Persuasive Essays

A Turkish Student and the Board of Regents In what ways can Iowa State University be improved? Responses to this question could vary widely depending on the background of the subject being interviewed. Perhaps an international student might suggest a new club or organization designed to acclimate foreign students to life on campus. However, John Couch, an international student from Turkey, had a much more unique response. Having a wide variety of friends isn't a large concern of his. He is more concerned with how the university is being run and the different boards and comities, in a particular the Board of Regents. John's opinion is that the Board of Regents isn't hearing the concerns of the students. In fact, they appear to be concerned less with the needs of the students and more concerned with the issues of funding. It is very unfortunate that the budget of the university has been cut, but the Board must still attempt to maintain a good relationship with the student body. The quality of education at Iowa State has suffered because of these budget cuts, and the Board has not posted any viable methods to attempt to replenish any of those lost dollars. When asked if he had any suggestions for going about this daunting task, John was unsure. There is definitely a need for more support to aid research, building renovations, and to allow for more teachers, reducing overall class sizes. John's opinion was influenced by his initial experiences at Iowa State. John spent two years in Iowa attending high school before choosing Iowa State. Even though when he graduated his family was still far away in Istanbul, Turkey, John was ready for college. He didn't know if he would fit in or if the other people would make fun of him, he just knew he was going to have fun and learn. John had heard about an organization called a fraternity and thought it sounded interesting. He would eventually join the university's chapter of Sigma Alpha Epsilon and would meet many new people.

Synthesis of Salicylic Acid and Potentiometric Determination of Its Purity and Dissociation Constant

Synthesis of Salicylic Acid and Potentiometric Determination of its Purity and Dissociation Constant ————————————————- Abstract The purpose of the study is to synthesize salicylic acid from the ester, methyl salicylate, and determine the acid’s dissociation constant and purity. The ester was converted to salicylic acid by base hydrolysis. The products were refluxed and recrystallized, to ensure maximum purity, and filtered, dried, and weighed. The melting point of the product was determined using a Fischer-Johns melting point apparatus. The acid then dissolved in separate beakers with 95% ethanol and water and titrated with 0. 050 M NaOH, previously standardized with potassium hydrogen phthalate, through potentiometric titration. The pH after addition of base was measured and plotted against the volume of titrant added using three different plots. Results show a 61. 0% yield and the melting point differed from the theoretical by a range of 3. 11-6. 83%. The pKa calculated was 2. 865, differing from the literature value of 2. 98, by 3. 86%. The theoretical purity of the sample was 100. 0%, which differed with the experimental one by 1. %; the experimental purity is 101. 7%. Potentiometric titration proves to be adequate in the determination of the acid dissociation constant and purity of a sample. Aside from that, the synthesis proved adequate given the high purity of the product. ————————————————- Keywords : acid dissociation constant purity melting point ester INTRODUCTION Potentiometric methods of analysis are based on measuring the potential of electrochemical cells without drawing much, appreciable current. For centuries, potentiometry has been used to locate the endpoint in most titration set-ups. Skoog, et al. , 2004). Potentiometric methods offer a myriad of advantages, its main advantage being its low operational costs. Voltmeters and electrodes are, generally, far cheaper than most modern scientific instruments. Models suitable for direct potentiometry in field work, away from the laboratory, are inexpensive, compact, and easy to use. Essentially nondestructive of the sample, i. e. , insertion of the electrode does not drastically change the composition of the test solution (except for the slight leakage of electrolytes from the reference electrode), electrodes are relatively free from interferences. Stable potential readings are attained fairly rapidly and voltages are easily recorded as functions of time. Finally, the wide range of analyte activities, over which some of the available indicator electrodes exhibit stable, nearly Nernstian responses, represents an important advantage (Day and Underwood, 1991). Potentiometric titrations involve measurement of the potential of a suitable indicator electrode as a function of titrant volume. This indicator electrode is speecific to the hydronium ion, H3O+. It offers adavantages over direct potentiometry in that it is not dependent on measuring absolute values of Ecell. This is due to having the measurement based on the titrant volume that causes a rapid change in potential near the equivalence point. This makes the process relatively free from the juction potential uncertainties as this potential remains approximately constant during the titration process. Instead, the titration results depend heavily on having a titrant with accurately known concentration. The instrument merely signals the endpoint and behaves like a regular chemical indicator. Aside from that, the reference electrode potential need not be known. Most importantly, ionic strength effects are not important in the titration procedure because the result is analyte concentration, even if the electrode responds to activities. The dissociation of a weak monoprotic acid is given by the equation HA – H+ + A– (1) [H+][A–] [HA] where HA is the monoprotic acid, and A– is its conjugate base. The corresponding equilibrium constant for this acid dissociation is defined as Ka = (2) Ka[HA] [A–] which, when seeking to find [H+], rearranges to [H+] = (3) Prior to the equivalence point, before any titrant was added and the analyte is the only species present in solution, the pH of the system is calculated from the concentration of that analyte and its dissociation constant. In the case where a weak monoprotic acid is being titrated with a strong base, subsequent addition of the titrant will cause a reaction to occur between the acid and the base. HA + OH– > H2O + A– (4) The presence of the acid and its conjugate base in solution will cause the formation of a buffer solution, which are solutions that resist a drastic change in pH, should a strong acid or base be added to the system. At these points, the slope of a constructed titration curve is at its minimum. This is the pre-equivalence point. There is a point during the pre-equivalence point region wherein both the acid and its conjugate base are present in equal amounts. This occurs when half of the acid has been neutralized, or when the titration is at the half-equivalence point. At this point, the buffering capacity of the system is at its maximum. Aside from that, simplifying Eq. 3 at this point by inspection, the [H+] is equal to that of the Ka. Taking the negative of the logarithm of both sides, one will be able to get the relation pH = pKa (Skoog, et al. , 2004). Thus, the dissociation constant may be computed through determining the pH at half-equivalence point. This experiment will use salicylic acid as the analyte. Salicylic acid, Fig. 1. Salicylic acid is a weak monoprotic acid, capable of releasing the acidic hydrogen connected to the –COOH group. The hydrogen of the phenol group is hard to release because the oxygen is stabilized by resonance. Salicylic acid is a naturally occuring substance, usually produced by plants. It is found mainly in the willow's leaves and bark. The pure acid possesses several useful medicinal properties. It is an antipyretic (fever reducer), analgesic (pain reliever) and anti-inflammatory (swelling reducer). However, pure salicylic acid makes for an extremely unpleasant medicine. Salicylic acid contains two acidic functional groups, the phenolic (C6H5OH) and the carboxylic acid (RCOOH) groups. These groups cause the acid to be an irritating substance that burns the delicate lining of the mouth, throat, and stomach, hence its esterification to acetylsalicylic acid or aspirin, before ingestion as analgesic (Reed College, 2009). Esterificaton is the process by which a carboxylic acid is transformed to an ester. Esters are organic compounds that are derived usually by reacting a carboxylic acid and an alcohol. The general formula for esters is with the RC=O group derived from the parent carboxylic acid, and the –OR’ group from the parent alcohol. The mechanism for the reaction of the alcohol and carboxylic acid to form the ester is as follows: Fig. 2. Mechanism of Esterification from a Carboxylic acid RCOOH and alcohol R’OH Esters may also be synthesized by reacting the carboxylic acid with other reagents such as SOCl2 to form the acyl chloride, which will then be treated with an alcohol in pyridine, to esterify it. Esters are among the most widespread of all naturally occuring compounds. Many esters are pleasant-smelling liquids that are responsible for the fragrant odor of fruits and flowers. For example, methyl butanoate is found n pineapple oil and isopentyl acetate is a constituent of banana oil. The ester linkage is also present in animal fats and other biologically important molecules. The chemical industry also uses esters for a variety of purposes. Ethyl acetate, for example, is commonly used as a solvent while many dialkyl phthalates are used as plasticizers to keep polymers from being brittle (McMurry, 2004) . Methyl salicylate is produced by many plants. It was first isolated from wintergreen leaves, Gaulthea procumbens, and is commonly known as oil of wintergreen. Fig. 3. Methyl salicylate An ester of salicylic acid and methanol, it masks one of the acidic hydrogens in salicylic acid by replacing it with a methyl (CH3–) group. Hence, it is a relatively unreactive compound that does not release salicylic acid efficiently into the body. It is, therefore, not an effective analgesic, or pain-killer. However, it is added to many products, notably for its fragrance, especially root beer and liniments. In order for it to be activated, methyl salicylate must be converted to salicylic acid by organic synthesis, specifically through saponification, a process not unlike that undergone by animal fats to become soaps (McMurry, 2004). In this experiment, salicylic acid will be synthesized from methyl salicylate by base hydrolysis. Its dissociation constant will also be measured through potentiometric titration. Likewise, the percentage of purity the salicylic acid used in the reaction will be likewise determined. METHODOLOGY In synthesizing salicylic acid, 1. 2 g of sodium hydroxide (NaOH) were dissolved in 7 mL water in a round bottom flask.. Half of a milliliter (0. 5 mL) of methyl salicylate was added to this mixture. The mixture was then efluxed for 15 minutes and cooled to room temperature. One-milliliter increments of 3 M sulfuric acid (H2SO4) were added until the formation of a white precipitate, salicylic acid. Half of a milliliter (0. 5 mL) of the acid was added to ensure complete precipitation of the product. The mixture was then cooled in an ice water bath with a temperature of at most 5 °C for the reaction to subside. The product was then filtered and rinsed with cold water, and recrystallized in wat er. The solids were then filtered on a pre-weighed filter paper and air-dried in the locker. When dried, the solids, along with the filter paper, were weighed and the melting point determined. Two hundred and fifty milliliters (250 mL) of 0. 50 M stock sodium hydroxide (NaOH) solution was then prepared. From this solution, 250 mL of 0. 050 M standard solution was prepared for the titration. This solution was then standardized with 0. 2000 g 99. 95% potassium hydrogen phthalate (KHP) and phenolphthalein as indicator to the pale pink endpoint. Two more trials were done. Three samples of pure salicylic acid were weighed at approximately 0. 000 g and placed in three separate 250-mL beakers. A minimum amount of 95% ethanol was then added to dissolve the acid, and was diluted with 50. 00 mL distilled water. The electrode was first calibrated such that it would relate the developed potential to the pH. At this point, the potential would be measured as pH when increments of the titrant are successively added. The base burette, pH meter, and magnetic stirrer were set up according to Fig. 6. Fig. 6. Potentiometric titration set-up A spin bar was place inside the beaker with the sample solution. The electrode was also positioned such that it would not get hit with the spin bar. The pH of the set-up was first measured prior to addition of base. For the first trial, 1. 00 mL of the titrant was added to the analyte and the pH recorded. This was done until the pH was 11. 50. From there, the equivalence point was approximated based on the volume of the titrant that caused a large change in pH. For the two succeeding trials, 1. 00 mL of the titrant was added to the analyte. At  ±5. 00 mL of the equivalence point, the volume of titrant added was reduced to 0. 0 mL increments. At  ±3. 00 mL and  ±2. 00 mL of the equivalence point, it was further reduced to 0. 20 mL and 0. 10 mL, respectively. The titration contnued beyond 5. 00 mL of the equivalence point using 0. 50 mL of titrant until the pH registered was 11. 00. RESULTS AND DISCUSSION Methyl salicylate reacts with a strong base in the following manner: Fig. 4. Base hydrolysis of methyl salicylate The methoxy group of the e ster is substituted by the hydroxide ion through nucleophilic acyl substitution. The hydroxide attaches itself to the carboxylic carbon. A fast proton transfer from the hydroxide to the methoxy group occurs such that the methoxy gets protonated and leaves the substrate. The sodium ions stabilize the negative charge of the salicylate ion predominantly found near the two oxygens of the ion. The solution was then refluxed to prevent loss of material and to prevent the inclusion of impurities in the product. After cooling to room temperature, 1. 00 mL of 3M sulfuric acid (H2SO4) until salicylic acid starts precipitating as a white solid. To complete the precipitation, 0. 50 mL of the strong acid was added to the mixture. At this point, the salicylate ion is protonated and the final product, salicylic acid, forms through the reaction: Fig. 5. Protonation of the phenolate and carboxylate groups of the salicylate ion The flask containing the precipitate was then doused in cold water to stop the reaction. Cold water was used in rinsing the solid after filtration to wash out impurities that were insoluble in the solvent. The solid was recrystallized in hot water. Dissolving the solids in hot water generally increases the solubility of the substances, hence the solids dissolve along with the soluble impurities. The mixture was then allowed to cool slowly. As the solution cools, the solubility of the compound (and of the soluble impurities) decreases, the solution becomes saturated with the desired compound, and the compound begins to crystallize. Because formation of crystals is a highly selective process that usually excludes foreign molecules, only crystals of the desired compound form. Because the soluble impurities are present in smaller amounts, the solution never becomes saturated with the impurities, so the impurities remain in solution even after the solution has cooled. Removing the solution from the crystals thus removes the solvent and the soluble impurities from the desired crystals. A final rinse of minimum ice water ensures the displacement of the impurities still clinging on the surface of the product (â€Å"Recrystallization,† accessed 6 Sept 2010). After it was recystallized, the solid was filtered again in a pre-weighed filter paper. The filter paper used in filtering the solid weighed 1. 0349  ± 0. 0002 g. The mass of the dried product and the filter paper was 1. 3610  ± 0. 0002 g; this means that 0. 3261  ± 0. 0003 g was synthesized. Theoretically, with methyl salicylate as the limiting reagent, the mass of salicylic acid should be 0. 5400 g. Computing for the %yield, would give 61. 0%. In the determination of the melting point, the observed range of the melting point was 150-156 °C. Comparing with the theoretical value, 161 °C, the relative error lies within the range 3. 11-6. 83%. Therefore, the synthesized salicylic acid has a high purity as exhibited by the magnitude of the relative error. This could justify the %yield given that recrystallization might have caused a loss of material due to the increase of the number of steps involved. It should be noted that in organic synthesis, steps leading to the target molecule do not give 100% yield, hence, increasing the number of steps would decrease the %yield. Aside from that, the low yield could be attributed to the accidental rapid cooling that occurred during the recrystallization process. In a titration curve, there are three important regions: pre-equivalence point, equivalence point, and post-equivalence point. For the titration of salicylic acid with NaOH, the pre-equivalence point is characterized by the dependence of pH on the concentration of salicylic acid. Let salicylic acid be HA; prior to addition of the base, the pH can be calculated by the concentration of HA and its acid dissociation constant, Ka. When the base is added, HA reacts with the hydroxide ion (OH– ) according to the Eq. 4 stated above. Therefore, one has a buffer solution comprised of salicylic acid and salicylate. At equivalence point, all of the acid has been converted into its conjugate base. This base will hydrolyze with water through the reaction A– + H2O > HA + OH– (6) reforming a small portion of the acid. At the equivalence point, the slope of the titration curve is at its steepest. The pH at this point is dependent upon the conjugate base formed and its base dissociation constant, Kb. Beyond the equivalence point, the post-equivalence point, the pH is dependent on the concentration of the excess titrant added. This is because the contribution of the conjugate base is very small and, therefore, negligible compared to that of sodium hydroxide. However, salicylate is still the dominant species of salicylic acid present in solution. A distinction between equivalence point and endpoint should be established when titrating. Skoog, (2004), states that the equivalence point is the point in titration where the amount of titrant added is chemically equivalent to that of the analyte in solution. The endpoint is a point during titration wherein an observable change signals that the amount of titrant added is chemically equivalent with that of the analyte. The endpoint may not necessarily coincide with the equivalence point, especially in neutralization titrations. It may come earlier or later than the equivalence point, depending on the indicator used. This difference pf volume at equivalent and endpoint is known as titration error. In potentiometric titration, no chemical indicator is required. Instead, the endpoint is characterized by the drastic change in pX, measured by the electrode. X may be H3O+, OH–, a cation or anion, or any substance participating in the titrimetric reaction (Day and Underwood, 1991). In this case, the volume of titrant that contributes to the greatest change in pH is the volume required to completely titrate the salicylic acid in solution. Thus, the increments of addition of titrant are narrowed down as the equivalence point is reached because that way, the equivalence point will not be missed. Aside from that, the exact volume of titrant required for complete reaction of the analyte would be detected. Prior to titration and dilution with water, the salicylic acid was dissolved with a minimal amount of 95% ethanol. Salicylic acid is sparingly soluble in water, a polar solvent that can hydrogen-bond with solutes that can hydrogen-bond with its molecules. This is due to the acid having more than 6 carbons increasing its non-polarity, although it has oxygen that can form hydrogen bonds with water (McMurry, 2004). Adding ethanol reduces the polarity of the solvent, facilitating dissolution of the acid. It was noted that some of the acid reprecipitated upon addition of water. Thus, a minimum amount of 95% ethanol was again added to dissolve the acid. In the experiment, the electrode was also not lowered while the bar was spinning as air bubbles would adhere on its surface causing an error in the measurement of pH. Constant stirring is important in potentiometric titrations, as in other types of titrimetric analyses. Stirring is done because it will cause the titrant to react not just with the surface of the analyte where it dropped but with the entirety of the analyte solution. This way, the reaction will go to completion and minimal error will be observed. The volumes used for standardization of NaOH with KHP as primary standard are tabulated in Table 2 in the Appendix. Standardization of sodium hydroxide gave 0. 04633 M NaOH. This value was used in the determination of the percentage of purity (%purity) of the salicylic acid sample. For the determination of the equivalence point volume, three plots were done for each trial. The first plot is the graph between pH vs. volume of titrant. The second is the first derivative plot with which ? pH/? V was plotted against V’, where ? pH and ? V are the change in pH and the volume added between two consecutive readings, respectively, and V’ is the average volume between two consecutive readings. The third plot is the second derivative plot between ? 2pH/? V2 and V†. The ordinate of the graph, ? 2pH/? V2, was obtained by taking the quotient of the difference between two consecutive readings of ? pH/? V, and ? V, whereas V† is the average of the two consecutive readings of V’. Only two trials were done because of the inadequacy of the time. The graphs for the first trial are: a) (b) (c) Fig. 7. Titration Curves for the First Trial. (a) pH vs Vtitrant; (b) ? pH/? V vs V’; (c) ? 2pH/? V2 vs V† MNaOHVNaOH at eq ptFWsalicylic acid Gsample The graph for the second trial may be found at the Appendix. Either of the three graphs of Figs. 7 and 8 may be used in the determination of %purity for each trial. The equation used for determining the %pu rity, specifically for this experiment is %purity = x 100 (7) Thus, the volume of titrant used at equivalence point is required for the calculation. The interpolated values of the volume at equivalence point are tabulated in Table 3 in the Appendix. Calculation of the mean %purity is 101. 7%, having an error of 1. 7%, as the theoretical value is 100. 0%. The pKa is based on the pH at half-equivalence point by virtue of the derivation of Eq. 3. Onle Figs. 7a and 8a may be used for the determination of pKa as the other four do not directly give the pH at each point. The interpolated values for the pH at half-equivalence point is tabulated at Table 3 in the Appendix. The experimental pKa is 2. 865. Therefore, the Ka of the acid, given Ka = –log[Ka] (7) or Ka = 10–pKa (8) is 1. 3646 x 10–3. The theoretical pKa is equal to 2. 98. Thus, the pKa value gave rise to a 3. 86% error. Statistical analysis of the results shows the following results: Table 1. Statistical Analysis of the Results | Range| Standard Deviation| %purity| 15. 7%| 11. 1%| pKa| 0. 21| 0. 148| | Relative Standard Deviation (RSD), ppt| Confidence Int ervals (95% confidence)| %purity| 109. 1| 101. 7  ± 99. 7 %| pKa| 51. 8| 2. 865  ± 1. 334| The RSD of %purity is relatively large such that the values have low precision. Aside from that, the confidence intervals for the mean is also large such that it almost has the same order of magnitude as that of the mean. This means that the mean exhibits very low accuracy. With regards to the pKa, the RSD showed a low value, only 51. 8 ppt, implying high precision amongst the values. On the other hand, the mean value shows low accuracy because of the magnitude of the confidence intervals. These errors could be attributed to the number of trials. Due to inadequate time, the group was only able to do 2 trials, one less than the prescribed number of trials. CONCLUSIONS The experiment aimed at synthesizing salicylic acid from methyl salicylate and determining the acid dissociation constant Ka of the acid along with its purity. Organic synthesis provided a 61% yield of the acid, a relatively low yield. However, the purity of the acid can be classified as high due to the observed melting point range’s precision with the theoretical one; the %differenceis only 3. 11-6. 38%. The results of the potentiometric titration show that the salicylic acid used was 101. 7% pure, a value greater than the purity, which is 100%. The Ka, expressed as pKa, obtained was 2. 865, 0. 035 units less than the theoretical value, which is 2. 98. Though the %differences are low, the accuracy of the computed values is questionable given that the confidence intervals for the %purity and pKa are  ± 99. 7 and  ± 1. 334, respectively. These errors can be attributed to the number of trials done, which is two, due to the slow stabilization of the pH meter readings that resulted in a long period of titration. Thus, it can be concluded that potentiometric titration is an effective way of determining the acid dissociation constant of a sample. It is recommended that a better pH meter be used in the measurement of the pH and that solutions used be titrated immediately. REFERENCES [1] Day, R. A. and A. L. Underwood. (1991). Quantitative Analysis. Sixth Edition. Prentice Hall, Inc. , USA. [2] â€Å"Experiment 3: Synthesis of Salicylic Acid from Oil of Wintergreen (Methyl Salicylate). † Laboratory Reference Manual Chemistry 201/202. Reed College. Accessed 6 September 2010 ;http://academic. reed. edu/chemistry/alan/ 201_202/lab_manual/Expt_salicylic_acid/background. html; [3] McMurry, J. (2004). Organic Chemistry. Sixth Edition. Brooks/Cole – Thomson Learning, CA, USA. [4] †Recrystallization. † University of Massachussetts. Accessed 6 September 2010 ;http:// www. chem. umass. edu/~samal/269/ cryst1. pdf; [5] Skoog, D. A. , D. M. West, F. J. Holler, S. R. Crouch. (2004). Fundamentals of Analytical Chemistry. Eighth Edition. Brooks/Cole – Thomson Learning, CA, USA. APPENDIX Gfilter paper = 1. 0349  ± 0. 0002 g Gfilter paper and dried product = 1. 3610  ± 0. 0002 g Gdried product = 0. 3261  ± 0. 0003 g %yield = 61. 0% Observed melting point range: 150-156 °C %difference = 3. 11-6. 83% 1 ° standard used;: potassium hydrogen phthalate (KHP) purity = 99. 95% Table 2. Standardization of NaOH Trial| Mass of KHP, g| Vtitrant, mL| Molarity, M| 1| 0. 2030| 21. 30| 0. 04664| 2| 0. 2175| 23. 00| 0. 04628| 3| 0. 2043| 21. 70| 0. 04608| Average Molarity, M| 0. 04633| Table 3. Sample Analysis Trial| Gsalicylic acid, g| Vtitrant at eq. pt. , mL| % purity| pH at half-eq. pt. (pKa)| 1| 0. 11 25| 16. 50| 93. 86| 2. 76| 2| 0. 1031| 17. 65| 109. 6| 2. 97| 3| -| -| -| -| Average pKa = 2. 865 Average %purity = 101. 7% Plot of the Second Trial: (a) (b) (c) Fig. 8. Titration Curves for the Second Trial. (a) pH vs Vtitrant; (b) ? pH/? V vs V’; (c) ? 2pH/? V2 vs V†

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