Triphenylmethanol Synthesized From Grignard Reaction Essay Example For College

Welcome to our essay sample on synthesis of triphenylmethanol from the reaction of the Grignard reagent! Here, you’ll find information on Grignard reaction procedure, TLC analysis, and other aspects of the experiment.

Abstract

In this experiment, triphenylmethanol was synthesized from the reaction of the Grignard reagent (phenyl magnesium bromide) with benzophenone (a ketone) and hydrolysis with HCL. The final product was purified and characterized using TLC and IR spectroscopy. The final product was weighed and the percentage yield calculated. All the apparatus for this experiment were kept completely dry as protons easily hydrolyze the Grignard reagent to a hydrocarbon. The melting point of triphenylmethanol was determined and checked against the recorded value to determine the purity of the product. The impurities generated in this reaction include biphenyl (from the reaction of phenyl radicals) and benzene from the protonation of the carbonation.

Introduction

Grignard reaction allows the formation of carbon-carbon bonds using organometallic intermediate (Grignard reagents). Grignard reagents are prepared by reacting magnesium metal with alkyl or aryl halides in aprotic solvents such as diethyl ether or tetrahydrofuran. They have a carbon-metal bond, which changes the polarity of a carbon atom from the partial positive charge (in aryl and alkyl halides) to the partial negative charge in Grignard reagents. They are strong bases as well as strong nucleophiles and readily react with electrophilic species. In the presence of acidic protons, water, or alcohol the Grignard reagent breaks its organometallic bond leading to the formation of a hydrocarbon. It is therefore important to maintain very dry conditions in reactions where the Grignard reagents are involved.

Electrophilic functional groups such as carbonyl-containing compounds, alkyl halides, and alcohols readily react with the Grignard reagent through nucleophilic acyl addition and nucleophilic acyl substitution mechanism. The reaction mechanism for the reaction between alkyl halides and Grignard reagent is similar to that involving a proton and the Grignard reagent. A new bond forms between the nucleophilic carbon of the Grignard reagent and electrophilic carbon of the alkyl halide. Aldehydes and ketones react strongly with the Grignard reagent via nucleophilic acyl addition mechanism forming alcohol as the product. The reaction of the Grignard reagent with different species is given in the figure below.

Mechanism of the reaction of the Grignard reagent with different species.
Figure 1: Mechanism of the reaction of the Grignard reagent with different species. (Addison, 447).

Nucleophilic acyl substitution reaction occurs when the starting material is an ester, amide, or acid anhydride. In this case, the electrons on the negatively charged oxygen atom are used to reform the carbonyl pi bond, thereby forcing the C-N or C-O bond of the ester, amide, or anhydride to detach as a leaving group generating a ketone intermediate. The ketone intermediate reacts with more Grignard reagent leading to the formation of a highly substituted alcohol.

Triphenylmethanol is prepared from benzophenone using a Grignard reagent e.g. phenyl magnesium bromide through nucleophilic acyl addition mechanism. “Magnesium alkoxide is formed as an intermediate, which is then hydrolyzed by HCL to give an ether soluble triphenylmethanol and a water-soluble salt of MgBrCl” (Addison 446). This occurs as shown by the reaction scheme below.

Preparation of triphenylmethanol
Figure 2.Preparation of triphenylmethanol (source; Addison, 446).

Carbon dioxide reacts with the Grignard reagent especially. A 1:1 ratio of carbon dioxide with phenyl magnesium bromide yields an MgBr salt of benzoic acid. The reaction of the salt with HCL yields benzoic acid and the water-soluble MgBrCl salt as shown in the figure below:

Reaction mechanism for the reaction of the Grignard reagent with carbon dioxide.
Figure 6: Reaction mechanism for the reaction of the Grignard reagent with carbon dioxide.

Below is the procedure for the preparation and characterization of triphenylmethanol starting with the preparation of the Grignard reagent (phenyl magnesium bromide) and subsequent reaction with benzophenone.

Procedure

Preparation of the Grignard Reagent

All the glass apparatus were first dried in the oven for about 10minutes.

Approximately 0.5g of magnesium turnings and a magnetic stir bar were put into a dry 100ml round-bottomed flask and then placed in the drying oven for 30minutes. The flask was then removed from the oven, clamped on to a ring stand, and fitted on the heating mantle. A reflux condenser was then inserted and the drying tube was immediately fixed to the top of the reflux condenser.

The flask was placed on the stirrer/hotplate and the contents allowed to attain the room temperature before proceeding. 3.5g of bromobenzene was added to a dry 50ml Erlenmeyer flask and dissolved in 5.0ml of anhydrous diethyl ether. A glass powder funnel was then used to transfer bromobenzene and ether to the Erlenmeyer flask where the contents were swirled to dissolve bromobenzene. Bromobenzene solution was transferred to the 100ml round-bottomed flask when it cooled using a funnel. A cloudy solution formed indicating that the reaction had begun.

An additional 10ml of ether was added to the flask using a glass funnel. Water was then allowed to flow through the condenser. The reaction was allowed to continue steadily for 15 minutes until all the magnesium dissolved and the contents turned brown/cloudy. The level of ether was kept constant in the flask by adding more as it evaporated. The condenser was replaced with the drying tube and the contents were kept aside.

Preparation of Triphenylmethanol

3.7g of benzophenone were placed into a clean dry 150ml beaker followed by 10ml of ether. The beaker was swirled gently until all the benzophenone dissolved. The condenser tube and the drying tube were removed from the reaction flask containing the Grignard reagent. A funnel was then placed on the flask and the stirrer switched on. Benzophenone solution was added dropwise to the flask using a dry glass pipette. 5-10ml of ether was used to rinse the beaker of ether, which was then added to the reaction flask. The condenser was then turned on and the reaction mixture gently refluxed for 25minutes. The mixture was allowed to cool to room temperature after which the drying tube and the condenser were removed.

5ml of distilled water was added to dropwise using a glass pipette as the reaction mixture was stirred. This hydrolyzed the alkoxy/magnesium bromide salt to form triphenylmethanol. 15ml of 5% HCL was added with continued stirring until the reaction subsided. The reaction mixture was transferred to a 200ml beaker adding more ether (5-10ml) to remove any residual product. Two layers separated in the beaker.

Product separation

The entire reaction mixture was transferred to a 125ml separatory funnel. The top layer (ether layer) contained the product while the bottom aqueous layer contained the magnesium bromide layer as the by-product. The water layer was drained into the beaker labeled “water layer”. 15ml of 5%aqueous sodium bicarbonate was added to the ether layer in the separatory funnel and shaken vigorously for 1-2minutes.

The mixture separated into water and ether layers on standing and the water layer was drained into the “water layer” beaker. 15ml of saturated sodium chloride was then added to the ether layer and the procedure above repeated. The water layer was drained to the respective beaker while the remaining ether layer was drained into a dry 100ml beaker labeled “ether layer.” 100mg of the drying agent (magnesium sulfate) was then added to the “ether layer” and swirled for some time. The drying agent was filtered off and the solution transferred into a pre-weighed clean and dry 125ml Erlenmeyer flask. Ether was removed from the product by placing the flask in a warm water bath. It was then stored in an open Erlenmeyer flask for one week to dry.

Trituration in Hexane of Crude Triphenylmethanol Product

The solid product was transferred to a 50ml Erlenmeyer flask followed by the addition of 10ml of hexane. The crude triphenylmethanol was gently but repeatedly pressed against the sides of the beaker in hexane (triturated) to promote dissolution of any impurities contaminating the product i.e. purification. The product was collected through vacuum filtration by washing it once with 10ml of hexane in a Buchner funnel. It was then placed on a watch glass to dry.

TLC Analysis of Triphenylmethanol

A TLC plate was prepared and labeled with three tick marks (1, 2, and 3) to analyze the synthesized products (1-benzophenone, 2-product, and 3-known triphenylmethanol). Approximately 10mg of the product was transferred to a vial and 1-2ml of ether was added to dissolve the product. The TLC plate was spotted with the product and solutions of the other known compounds provided. The plate was developed using 90:10 hexane: ethyl acetate. The TLC plate viewed under UV-light and in the iodine chamber, circling the observed spots with a pencil. The Rf values for all the spots observed were calculated.

IR Spectroscopic Analysis of Triphenylmethanol

An IR scan was performed on the product and all major peaks (in cm-1) were recorded for functional group identification.

Weight and Melting Point Determination of Triphenylmethanol

The dry product sample was weighed and the percentage yield was calculated. For melting point determination, the thermometer of the melting point apparatus was first calibrated using benzoic acid (M.p =1220C). The melting point of the product was then determined and recorded. It was compared with the standard melting point of triphenylmethanol to determine its purity.

Work Cited

Ault ,Addison. Techniques and experiments of organic chemistry. 6th ed. New York: Prentice Hall, 1998. Print.

Florida’s Medicaid Program History

Rationale

Florida’s Medicaid reforms initiated in 2006 aimed at statewide coverage expansion of the managed care system. In 2005, former governor, Jeb Bush, signed into law a federal waiver proposal to move recipients from the fee-for-service model to managed care (Senior, 2016). The rationale for this healthcare reform was to expand coverage to over 4 million uninsured Floridians to lower the percentage of the uninsured (Senior, 2016).

Adoption of the Reform

Managed-care plans were adopted in Florida after the approval of the federal waiver proposal on June 3, 2005. The permission followed Governor Jeb Bush’s push for a ‘Section 1115’ Medicaid Waiver from the national government to reform the state’s Medicaid program (Senior, 2016). The goal was to promote competitive health care benefits through risk-adjusted premiums for recipients. The resulting plans would offer the mandated services but allow for adjustments related to payment, period, and range of products Floridians would receive.

Since 2006, children from poor households, expectant mothers, disabled persons, and the elderly were enrolled in a Medicaid waiver pilot implemented in five counties (Senior, 2016). The recipients could receive primary and acute care services through managed care or provider-funded organizations. The program also included flexible, cost-shared benefits for the low-income pool (LIP). It entailed mandatory enrollment of the elderly, disabled persons, and poor households, and foster children (Senior, 2016). These groups qualified for full Medicaid benefits. Presently, under this plan, persons with long-term care (LTC) needs are eligible for post-acute and primary care benefits (Senior, 2016). These services are offered through Health Maintenance Organizations and Provider Service Networks engaged in the LTC program as prescribed in the waiver.

After prolonged discussions with the Center for Medicaid and Medicare Services (CMS), Florida received the approval to shift to managed care plans in 2013. Subsequently, a statewide expansion of this program commenced with the launch of the Statewide Medicaid Managed Care (SMMC). The SMMC program comprises two parts: “Long-term Care (LTC) and Managed Medical Assistance (MMA)” (Senior, 2016, p. 2). The first component expands LTC services to all Medicaid-covered populations through the Nursing Home Diversion program (Senior, 2016). In 2013, the state began a phased transfer of Medicaid recipients to LTC managed care, completing it in 2014. The MMA program increased the coverage of the pilot waiver from five sites to statewide health care. Under this plan, comprehensive Medicaid benefits are available to all participants, except those enrolled in the “family planning programs, breast and cervical cancer services, and pediatric care” (Senior, 2016, para. 7).

Since the 1990s, Florida has been implementing a case management plan known as MediPass (Senior, 2016). Under this program, about 600,000 enrollees could access care from 5,000 healthcare organizations. Those with chronic conditions received services from subcontracted providers. However, as of August 2014, the state began to move MediPass beneficiaries to the managed care program (Senior, 2016). Under this program, Medicaid-covered children are eligible for either DentaQuest or MCNA Dental for their dental care needs (Senior, 2016). Florida’s MMA aims to improve quality, enhance access, and reduce spending. It also seeks to strengthen care coordination, expand benefits for enrollees, and manage costs.

Funding Structure

The Medicaid budget is financed through state and federal funds – a joint funding structure. This financing model ensures better responsiveness to state priorities and needs. In 2014, Florida spent $23bn on its Medicaid program with $9.5bn coming from state funds (Snyder & Rudowitz, 2015). The remainder ($13.5bn) came from the federal disbursements through the Federal Medical Assistance Percentage (FMAP), enhanced matching rates, and Disproportionate Share Hospital (DSH) programs. FMAP matches national allocations with each $1 spent by the state on Medicaid. Thus, this funding model responds to the actual expenditures and needs of the beneficiaries. In 2014, for every dollar Florida allocated to this program, the central government gave $1.43 (Snyder & Rudowitz, 2015). The statewide expansion of Medicaid calls for enhanced matching rates to cater for the high number of beneficiaries. In particular, the Affordable Care Act (ACA) extends the eligible populations, resulting in additional costs. According to Snyder and Rudowitz (2015), federal funding of the ACA Medicaid expenditures stands at 100%, to be phased down to 90% by 2020. There is also an administrative matching rate (<5% of the budget) related to costs incurred by the state in the enrollment processes.

DSH payments are given to healthcare organizations serving a disproportionate number of Medicaid recipients and poor Floridians without medical insurance. This form of financing has played a role in stabilizing the ‘safety net’ of providers. However, under the ACA, DSH payments are set to decline beginning in 2018 due to lower “uncompensated care costs” related to expanded Medicaid coverage (Snyder & Rudowitz, 2015, para. 12). In addition to federal funds, the state also contributes to this program. The non-federal funds going into Medicaid primarily comes from the state coffers. In 2014, Florida appropriated $9.5bn (41%) to Medicaid spending with the remainder coming from the federal allocation (Snyder & Rudowitz, 2015). Flexibility is required to cater to competing priorities. Over the years, Florida has enhanced its share of the Medicaid budget through provider capitation.

Impacts

The Medicaid Reform Program has had a profound effect on health care coverage and delivery in Florida. Between 2006 and 2012, about 1.8 million persons (uninsured and underinsured groups) received inpatient care with another 10.8 million benefitting from outpatient services in Floridian hospitals (Duncan, Hall, Harman, Bell, & Kinsell, 2015). Those served by non-hospital providers rose by 255,500 to 694,300 individuals over the same period. Hospital care included diagnostic and radiology services, surgeries, emergency care, etc. The $35 million LIP program has had a significant impact on access to care by poor households and Medicaid eligible persons. About 60% of LIP’s tier one and tier two initiatives have impacted health care utilization by these populations (Duncan et al., 2015). The number of patients receiving Enhanced Benefits Account (EBA) credits for engaging in healthy behaviors – physician visits, PSA tests, etc. – has increased in Florida, earning them $37 million between 2010 and 2014 (Duncan et al., 2015). There has also been a growth in services, providers receiving LIP, and enhanced matching rates and health care utilization.

The expansion has had an impact on healthcare costs in Florida. Now, the financial burden of providing care is shared between the hospital and non-hospital organizations. Thus, the expansion has reduced the cost of uncompensated care that was previously borne by hospitals alone. The estimated savings from the expanded coverage are about $1.3 billion (Duncan et al., 2015). The outcome of the shift to managed care is improved solvency in Florida’s health care system. The expansion came with increased Medicaid allocation – $9.5bn in 2014. The federal funds have fuelled the growth of Florida. Medicaid injected $8.9 billion to the local economy and created over 71,000 employment opportunities in 2014 (Duncan et al., 2015).

References

Duncan, R. P., Hall, A. G., Harman, J. S., Bell, L. L., & Kinsell, H. S. (2015). Florida Medicaid reform evaluation: Final low income pool milestone statistics and findings report for DY8: SFY 2013–14. Gainesville, FL: University of Florida.

Senior, J. M. (2016). Florida Medicaid: Statewide Medicaid managed care. Web.

Snyder, L., & Rudowitz, R. (2015). Medicaid financing: How does it work and what are the implications? Web.

Development And Implementation Of Training Programs: Executive Team Roles

The executive team that works in the organization can contribute to the development and implementation of training programs significantly. It is important to note that the leaders’ knowledge and experience can be used actively when it is necessary to design or improve training programs in a company (Lee-Kelley & Blackman, 2012).

Therefore, much attention should be paid to identifying specific roles that executives can perform while collaborating with training directors and developing a new program. The leaders’ participation in the process of executing training programs can have significant benefits for the organization. From this point, it is important to distinguish possible roles that the executive team can take while participating in planning, implementing, and assessing training programs and formulate recommendations regarding the effective involvement of executives in the training process.

Potential Roles for Executive Team

Executives can play important roles in influencing the process of implementing training programs because these leaders determine goals for the company’s progress and employees’ development. They allocate required resources and control the realization of tasks with the focus on outcomes (Harnett & Powell, 2015). From this perspective, it is possible to concentrate on the discussion of following roles that are determined for leaders in an organization: goals and expectations’ setting, decision-making, sponsorship, support, control, and evaluation.

The process of planning and developing training programs is based on goals and expectations that are set by executives. Organizational leaders evaluate the employees’ performance and the overall outcomes, and they compare the results with the goals related to the performance improvement. Thus, they can indicate changes in the working process that are made in order to achieve higher results (Jackson, 2012). The program to train employees and improve their work should be developed according to the executives’ expectations and formulated goals. At this stage, executives are also responsible for making decisions regarding the implementation of this or that program.

In order to execute the program, leaders need to provide the financial resources and required materials. Training directors are responsible for planning the budget for the program, but the leaders’ task is to provide the necessary sponsorship. The effectiveness of the training program can depend on the number of resources that the leader is ready to propose for the program’s implementation, and this step should be regarded as the investment in the talent’s development (Bartos & Shetty, 2013).

Executives also provide the material support during the implementation of the training program in order to guarantee its success. Finally, the other important roles of the executive team in training employees are the control and evaluation of training results. The primary control is realized by the training director, but executives monitor and evaluate the training program with reference to reports and analysis of outcomes. The conclusion regarding the program’s effectiveness is made by the executive.

Recommendations regarding Executive Team’s Involvement in Training

While focusing on potential roles of executives in the development and implementation of training programs, it is also possible to identify additional areas where leaders can apply their knowledge and contribute to the improvement of training initiatives in an organization. When executives plan to be actively involved in the procedure of organizing training in a company, their roles can be broadened, and the degree of the leader’s control over training also increases. It is possible to recommend taking the following steps:

  1. The executive team should complete the complex assessment in order to identify the areas for improvement in the employees’ performance and operations, as well as possible gaps (Dewhurst, Harris, Foster-Bohm, & Odell, 2015).
  2. The executive team should divide employees who need training into categories, including human resource managers, unit managers, IT specialists, and department employees among others. The number of categories depends on the number of departments and roles that employees perform.
  3. In order to guarantee the high level of retention and the high-quality performance, the executive team should determine specific goals for each group of employees or for separate units according to the assessment of their needs and successes.
  4. It is important to assign each member of the executive team to become a coordinator of the training program development, execution, and evaluation for separate training groups. In this case, the planning, control, and evaluation of the training process will be a well-organized process, and executives will be able to monitor changes effectively (Rogers, 2013a).
  5. The CEO can collaborate with the training director while allocating resources and evaluating the financial reports that demonstrate the effectiveness of training.

The development of these steps is supported by the prediction of the realistic contribution that the executive team can make to the implementation of training programs. It is possible to expect that leaders are interested in setting goals for the training in order to guarantee the achievement of the targets for the performance and work efficiency (Phillips & Phillips, 2016).

It is also possible to expect that the executives can spend much time in order to control the use of resources and evaluate the program’s outcomes. The reason is that leaders analyze how many resources are spent on training and what results are observed (Rogers, 2013b). In addition, the executive team is interested in receiving the detailed reports related to the training evaluation.

Conclusion

The members of the executive team should not only be informed regarding the development and implementation of training programs in their organizations, but they should be involved in the process. The importance of training for the organization is high, and training directors should collaborate with the CEO and other executives in order to guarantee the efficient use of sources, the reduction in costs, and the increase in positive outcomes.

Potential roles of executives include goals setting, sponsorship, and evaluation of results among others. The expected roles of leaders can include the participation in planning programs, the coordination of programs, and the control over the program implementation with reference to the further evaluation of observed changes.

References

Bartos, N., & Shetty, D. (2013). The importance of planning training into projects. Training & Development, 40(4), 12-16.

Dewhurst, D., Harris, M., Foster-Bohm, G., & Odell, G. (2015). Applying the Kirkpatrick model to a coaching program. Training & Development, 42(1), 14-22.

Harnett, D., & Powell, A. (2015). When evaluation precedes assessment. Training & Development, 42(1), 18-26.

Jackson, J. (2012). Training evolution. Training & Development, 39(2), 34-36.

Lee-Kelley, L., & Blackman, D. (2012). Project training evaluation: Reshaping boundary objects and assumptions. International Journal of Project Management, 30(1), 73-82.

Phillips, J. J., & Phillips, P. P. (2016). Handbook of training evaluation and measurement methods. New York, NY: Routledge.

Rogers, S. S. (2013a). Change management: Your roadmap to training success. Training & Development, 40(3), 4-10.

Rogers, S. S. (2013b). Great expectations: Making ROI successfully work for you. Training & Development, 40(1), 8-19.

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