Nitration of Methyl Benzoate: A Lab Report

Nitration of Methyl Benzoate: A Laboratory Report


The major aim of the experiment was to substitute the hydrogen atoms on the methyl benzoate ring with a nitro group to obtain a pure product of methyl 3-nitrobenzoate after recrystallization. Nitration of Methyl benzoate follows the principles of an electrophilic aromatic substitution reaction. As such, the attachment of the nitrogen group depends on the type of pre-existing functional groups on the ring. In this case, the existence of the carbomethoxy group determines whether the nitrate group is ortho-para directed or meta directed. The reaction proceeds as shown below. After completion of the reaction, the experimental yield of Methyl 3-nitrobenzoate is determined and compared with the theoretical yield. Besides, the melting point of the product was determined. A detailed laboratory report for the experiment is presented herein.

Figure 1: The structural formula for the nitration of methyl benzoate (Drawn using ChemDraw Ultra, version 12.0).


Nitration reactions involve nitro group addition or substitution with pre-existing functional groups such as methyl in organic compounds. In ortho-para electrophilic aromatic substitution reactions, electron-donating functional groups, which are attached to the ring, are used as the directors while electron-withdrawing ones are responsible for meta directed substitution reactions. The figure below illustrates the difference in these types of reaction products. Furthermore, in meta directed products, the substituent is attached to the third Carbon in the ring while in ortho-para, the attachment is in the second or the fourth carbon atom.

Figure 2: Illustration for ortho,para, and meta directed substitutes in electrophilic aromatic substitution reactions (Drawn with ChemDraw Ultra, version 12.0).

Nitration of methyl benzoate begins with the formation of a nitronium ion (NO2+) from the reaction between sulfuric acid and nitric acid. Since the ion is positively charged, it is more attracted to a neutral carbon atom on the ring where it substitutes the hydrogen atom. The ion is formed via the interaction of the two strong acids as shown in the reaction below.

Figure 3: Reaction equation for the formation of the nitronium ion (Drawn with ChemDraw Ultra, version 12.0).

Sulfuric acid then protonated methyl benzoate to form resonance intermediaries that have a high density of electrons at the meta position (Williamson & Masters, 2010). The nitronium ion then attacks the third carbon to form an arenium ion intermediate, which undergoes proton transfer to the basic bisulfate ion to give methyl 3-nitrobenzoate as the end product of the electrophilic reaction. In meta directed electrophilic aromatic substitution reactions, the electron withdrawing group, in this case the ester, deactivates the benzene ring for the reaction making the ortho and para positions to be positively charged. The two positions further destabilize the carbon that is next to the carbomethoxy group. This leaves the mata position, which is neutral, to be more reactive compared to the two positively charged carbons. Experimentally, the reagents must be kept in a cool environment to protect the nitro group from being removed. Through recrystallization process, the resultant product is purified (Williamson & Masters, 2010). 

As a laboratory precaution, it is important to avoid contact with the two strong acids, sulfuric and nitric. In case of an accident that leads to spillage of these chemicals, it is advisable to neutralize with sodium bicarbonate powder and immediately clean up (Williamson & Masters, 2010). The practical must also be carried out in the presence of at least one skilled laboratory technician who must be informed in case of accidents and other risky instances. Protective wear is also essential equipment during the experiment. For instance, the addition of nitric acid to organic substances can react rapidly and is a highly exothermic reaction. As such, the experiment was carried out with a keen adherence to the laboratory rules and cautions involving the reagents used.

Figure 4: A balanced chemical reaction for the nitration of Methyl Benzoate (Drawn with ChemDraw Ultra, version 12.0).

Results and Calculations

Table 1: The amount of reactants used in the experiment (Provided in the experiment procedure).

SubstanceAmount usedMolecular weights
Nitric acid0.2 mL63.01 g/mol
Sulfuric acid0.2 mL98.079 g/mol
Additional Sulfuric acid 0.6 mL98.079 g/mol
Methyl benzoate0.3102g136.14792 g/mol
Methanol0.5 mL32.04 g/mol

Table 2: Amount of substances produced after the experiment (experimental results).

SubstanceAmount produced
Crude methyl 3-nitrobenzoate 0.5 g
Pure methyl 3-nitrobenzoate0.0733g
Theoretical melting point of methyl 3-nitrobenzoate78 0C
Melting point range of methyl 3-nitrobenzoate produced77.3-80.3 0C
Theoretical yield methyl 3-nitrobenzoate0.0022784042 moles
Actual yield of methyl 3-nitrobenzoate produced0.0004049723 moles
Percentage Yield 17.76 %

From the equation:

The mole ratio for methyl benzoate: methyl 3-nitrobenzoate is 1:1

Amount of methyl benzoate used       = 0.3102g

Moles of methyl benzoate used          =

                                                = [0.3102 g ÷ 136.14792 g/mol] moles

                                                = 0.0022784042 moles of C6H5COOCH3

Because of the mole ratio of 1:1, the number of moles of methyl benzoate equals the number of moles of methyl 3-nitrobenzoate produced.

Therefore, the number of moles of C6H4COOCH3NO2 = 0.0022784042.

But from the experiment, 0.0733 grams of methyl 3-nitrobenzoate was produced.

Moles of C6H4COOCH3NO2 =

                                                = [0.0733g ÷ 181.14 g/mol] moles

                                                = 0.0004046593 moles of C6H4COOCH3NO2 produced

% yield = Percentage yield = { } ×100%

                                    = {0.0004046593 ÷0.0022784042} × 100%

                                    = 0.1776064580 × 100%

                                    = 17.760645806%

                                    = 17. 76%

From nitric acid point of view, the number of moles used can be calculated as shown below.

Moles of nitric acid =

Mass of HNO3used = 0.2 mL, which translates to 0.2 grams since 1 mL= 1g.

Moles                          = [0.2g ÷ 63.01g/mol] moles

                                    = 0.0031740993 moles of HNO3

Since the mole ratio of HNO3: C6H4COOCH3NO2is 1:1, the possible yield of methyl 3-nitrobenzoate is 0.0031740993 moles. Therefore, methyl benzoate is considered as the limiting reagent of the experimental reaction. Therefore, the theoretical yield is calculated by considering the least possible number of moles of the product, which is as a result of the limiting reagent’s contribution. The theoretical yield for the experiment is 0.0022784042 moles of C6H4COOCH3NO2.

Discussion and Conclusion

In the reaction for nitration of methyl benzoate, the nitro group substitutes the hydrogen atom at the meta position of the benzene ring. This is because the carbomethoxy functional group in the methyl benzoate compound is an electron-withdrawing group. The reaction took place in a fume hood as a precaution due to the corrosive and reactive nature of strong sulfuric and nitric acids. In the identification of the experimental product, the melting point was determined. The range of 77.3-80.3 0C is within the theoretical value for melting methyl 3-nitrobenzioate, which should range between 78-800C according to literature works. The slightly lower melting point of 77.30C is due to persistent impurities that were not excluded during crystallization and recrystallization process using 0.5 mL of methanol. It is possible that there were side reactions that led to the formation of ortho and para directed substituents in the product despite being unfavorable compared to meta positioned major product. These bi-products might have been formed as isomers from the side reaction. This is the likely reason for a slightly higher value of the melting point range with a deviation of 0.30C.

The ester was used as an electron-withdrawing group in the electrophilic aromatic substitution reaction that led to nitration of methyl benzoate compound with a nitric acid. The ester deactivated the benzene ring against reacting with the nitonium ion, which was formed from the interaction between sulfuric and nitric acids. Ortho and para positions attained positivity that was least preferred by the ion during the electrophilic attack. The most favorable position, the third carbon atom from the carbomethoxy position in the ring was thus preferred for substitution. The hydrogen atom was substituted with the nitronium ion to for methyl m-nitrobenzoate compound as the end target product.

The major product of the experimental reaction is methyl 3-nitrobenzoate. This is because of the registered melting point, which is within a closer range with the theoretical value and slightly lower i.e. 77.3-80.30C as compared to the expected 78-800C. Ortho-para directed methyl nitrobenzoate products are expected to show a higher melting point than the expected range. This is because of the activation of the aromatic ring by the electron donating groups e.g. the halogen functional groups, which leads to the formation of a highly negative center as a site for reaction with the positively charged electrophiles. Eventually, it requires more energy to break the bonds between the atoms in an ortho-para directed product due to relatively stronger electronegative forces.

The percentage yield for the experimental reaction was recorded as 17.76%. This is a low value; hence the procedure used cannot be used for commercial production of methyl 3-nitrobenzoate. The method used to purify the end product is effective and efficient. This is because of the melting point value that was almost reproduced. The range attained is a characteristic feature for methyl m-nitrobenzoate with a slight deviation. Despite the workability of the recrystallization method employed in the experiment, slight variations in melting point ranges indicate the presence of persistent impurities. The experiment was successfully carried out, proving the hypothesis that the reactants used and the conditions would lead to nitration of methyl benzoate to methyl 3-nitrobenzoate via an electrophilic aromatic substitution reaction.


Williamson, K. L., & Masters, K. M. (2010). Macroscale and microscale organic experiments.Boston, Mass: Cengage Learning


Tired of Guidelines or Lack Time to Work on Your Paper, Get Original Custom Research Paper Writing Service

Thecustomwriting.com research paper writing service has saved thousands of students from stressful college life. Writing a custom research paper may be challenging, considering it has to be plagiarism-free. And it is better not to do your project than to hand in plagiarized work or hurriedly complete it if you do not have time.

Academic integrity is so vital that you may get a suspension or an expulsion because of a copy-pasted work. Writing a custom research paper requires research and writing skills to produce original content. Here are essential things to know about getting the best and legit assignments help websites.

Perfection is vital

Every website will promise you that they produce high-quality work. However, you put your money for your end-of-semester paper only to get a pass. You must learn how to identify the best writing service before committing.

Thecustomwriting.com produces quality content at all times. Rather than a quality promise, quality assurance is what you should consider before hiring a research writer. Best writing services are reliable. You don't want to partner with a cheap research paper writing service that will deliver poorly written essays hours after the due date.

Quality writers are part of the best writing service. A company that has untrained writers will fail you. Before committing, ensure that the people who will write your paper are academicians and professionals. It would help if you had a writer who will be prompt to respond to your questions and follow instructions. Writers who do not fear to ask for clarification where they don't understand are the best for you.

Beware of Scammers Posing to Provide Custom Research Paper Writing Service

It may take time and effort to find a legit custom research paper writing service. Most of the websites claiming to offer writing service trades your paper with another student. For example, if you order your paper today to submit it next week, you may find that another student has already handed over the same document.

Your money is gone, you have no paper to submit, and the deadline is in two hours. You can only sit and cook up some stories for your lecturer. Otherwise, wait for a penalty or suspension.

Others will give you half-baked papers in the name of cheap essays. Apart from reselling your paper, some companies will offer you copy-pasted work. If you don't have tools such as Turnitin or Copyscape to check plagiarism, you may find yourself in the dean's office explaining why you copied your work from the internet word-to-word.

We offer one of the best research paper writing services in the USA and the U.K.

You won’t regret choosing Thecustomwriting.com to handle your research. Your project is an essential part of your academic work. It determines whether you will move on to the next semester or if your name will appear on the graduation list. Do not gamble your education by hiring any cheap essay writing website you find on the internet. Look for a custom research paper writing service reviews before commit.

Avoid scandals by hiring Thecustomwriting.com. Count yourself lucky if you are reading this article. You are in the right direction in finding the writing service for your paper. Though many websites could have frustrated you, Thecustomwriting.com is committed to providing you with reliable service for your paper.

Thecustomwriting.com offers quality services at affordable prices, and they deliver your work on time. They have native English writers that write your paper using the correct language.

Plagiarism Free Custom Research Paper Writing Service

Our writers understand the seriousness of writing plagiarized papers. Every institution has regulations that govern how a research project is conducted. Universities and colleges take plagiarism as gross misconduct. The best writing services are those that will deliver plagiarism-free papers.

Plagiarism involves, among others, copying a published work and delivering it to your lecturer as your own without acknowledging the sources.

Another way your work can be plagiarized is the failure to include the source of your content in a research paper. If you are using someone's thought, you need to include a reference and in-text citations to show that you are using another scholars' worker.

It's a gross mistake to write a five-page paper without a single source unless the paper's nature does not require you to rely on any sources. Here are some tips our writers use to avoid accidental plagiarism:

  • Cite direct quotes, statistics, and paraphrased content.
  • Ensure that all in-text citations are included in the biography and vice versa.
  • Directly quoting not more than 2% of the paper, if quoting is necessary (some papers are exempted from this rule, especially literature).
  • Stick to high authority, scholarly sources. Our writers will hardly paraphrase content from third party blogs and other questionable sites.
  • Consider Buying A Custom Research Paper from Thecustomwriting.Com

    Consider hiring an expert essay writer if you are not sure about your capabilities. Referencing and citations can be challenging, especially if you try to do it for the first time. It's even harder when your lecturer asks you to use a hard referencing style. For example, Harvard requires you to include page numbers, dates, and the author's name in the text. If you have several papers with a strict deadline, you should consider hiring a custom research paper writing service to help you work on your essays.

    However, ensure the website you want to hire offers legit writing service. A good website should at least charge for its services. You will find many websites willing to provide you with free services. No one is that idle to sit and write a paper for free. Sites that provide free or cheap services hooks you when you least expect.

    Also, consider the price of writing a paper. Though cheap essays are of low quality, other sites may have inflated prices for their rate, making you needlessly break your bank.

    Thecustomwriting.com understands the need for a fair and reasonable price for most students. We know that most students need service, but they do not have enough resources. We, therefore, offer quality service that you can afford.

    Benefits of using custom research paper writing service

    If this is your first time considering using a custom writing service, the first thing is to know why taking such an action is the best. Choosing Thecustomwriting.com ensures professional writers handle your paper. Letting a qualified person handle your project can boost your grade. You cannot afford to fail in the upcoming end-of-semester project. In any case, your progress to the next level will be determined by how well you perform in your essay.

    Thecustomwriting.com ensures the timely delivery of your work. The good thing about legit essay writers is that they can write your essay within the shortest time possible, with one page taking up to one hour at most. It doesn't matter what time you want your work done: Thecustomwriting.com is always ready for a task.

    We will give you a paper written explicitly for you. We will ensure that your paper is not delivered to someone else.

    Come to think of this; if five of your classmates decide to order an essay for the same class, five writers will be assigned to work on different papers instead of paraphrasing one paper and sending it to five of you.

    Frequently Asked Questions (FAQ)

    Do subject specialist writers handle my research paper?

    It's our responsibility to ensure that someone from your field handles your paper. Our company has enough writers from every discipline. We provide only a research writer qualified in your subject to handle your paper. After placing an order, the first step is to screen the question and requirement and match it with the best writer. The less qualified writer has a college diploma, and they only handle high school papers. All other writers are bachelor, masters, and PhD degree holders.

    Are your researchers qualified enough to know the core of the research?

    We commit to quality content. We understand that failure to deliver quality service will result in the loss of clients. Therefore, we only hire qualified writers who have an in-depth understanding of your paper. Whether you want quantitative research done using Chi-square or qualitative research, Thecustomwriting.com’s writers will comfortably handle any discipline or type of paper. Besides, we offer research paper service from college to PhD. Therefore, we cannot afford to have unqualified writers. Our researchers take every instruction keenly when writing your essay.

    Should I worry about order placement?

    There is nothing to worry about placing your order. Our platform has a simple, user-friendly interface that enables you to navigate to different functionalities with ease. We offer quality custom research paper writing services; thus, you don't have to worry about getting value for your money. Besides, you can track your order's progress. Our system progressively send you email notifications regarding every stage of your orders' progress; thus, you don't even have to log in to track down your order. You will also see the progress on the dashboard when you log in. Moreover, our support team will contact you when the writer needs any clarification.

    Can I have direct communication with the writer after the order placement?

    Our system is designed in such a way that it allows you to communicate with your writer directly. We understand the need to clarify things yourself to the writer. Furthermore, our support team is available 24 hours to ensure that urgent matters are communicated swiftly with the writer.

    Will I get any discount on recommendation?

    The answer is yes. We value your efforts and trust to recommend us to your friends. We will offer you a discount on your next order if a client mentions your email when placing an order.

    What guarantees should customers look for?

    We have a written list of what we guarantee our clients in our terms. We guarantee the quality, confidentiality, free revision, original content, and timely delivery. We also guarantee money-back if, in the unlikely event, you are not happy with the quality of the paper.

    What makes a reliable writing company?

    It's easy to know a reputable company. First, they are transparent about their services. They offer multiple methods of communication and have qualified writers. Most importantly, they deliver your work on time, deliver original content, and honour what they have guaranteed.

    Why should customers not opt for cheap essay writing services?

    Cheap essay services will only waste your time. They have foreign writers who will produce plagiarized content full of grammar errors. You will waste your precious time waiting for a paper that you can't give your lecturer.

    Is buying essays online safe?

    It's safe to buy your essay if you take the right precaution. Before putting your money on a strange site, explore the website to see whether you will get customer reviews. They will help you make the right decision.

    How do I hire someone to write an essay for me?

    These are common questions with most clients. It's effortless to get a professional writer. The first step is to identify a custom research paper writing service that is legit and sign up. After that, they will guide you on how to place your order and get a writer. Some companies will allow you to choose a writer for yourself or choose a writer for you.

    What types of writing services can I order online?

    Our website offers a variety of legit essay services. We provide any academic assistance, including research projects, assignments, and admission letters. Visit our website to see what each service entails.

    What benefits and additional features do Thecustomwriting.com services offer?

    We offer several free services to our customers. We offer free revision, a discount on your first order, and free pages such as references and cover pages. Also, we have a quality control department that ensures that all papers are of high quality before delivering them to you.

    Do websites maintain your privacy? Are orders secured?

    Your privacy is our top priority. You will be recognized by your I.D. assigned to you after signup instead of your name. The only person who can access your account is you or anyone else you give your password. Your payment is through a third party. Therefore, your personal information will never reach our site without your consent.

    What are the pros of ordering from custom writing services?

    You get quality papers. We have writers with decades of experience delivering quality papers worth the client's money and much more. We understand your power to influence our progress. Your paper will be delivered on time and written by professional writers.

    Hire a professional writer

    Now that you know what to look for when considering the custom research paper writing services, it's time to try us. Sign up and get a discount on your first order. You don't have to worry about quality, timely delivery, and price. We know they are essential to you.

    Calculate your order
    Pages (275 words)
    Standard price: $0.00
    Client Reviews
    Our Guarantees
    100% Confidentiality
    Information about customers is confidential and never disclosed to third parties.
    Original Writing
    We complete all papers from scratch. You can get a plagiarism report.
    Timely Delivery
    No missed deadlines – 97% of assignments are completed in time.
    Money Back
    If you're confident that a writer didn't follow your order details, ask for a refund.

    Calculate the price of your order

    You will get a personal manager and a discount.
    We'll send you the first draft for approval by at
    Total price:
    Power up Your Academic Success with the
    Team of Professionals. We’ve Got Your Back.
    Power up Your Study Success with Experts We’ve Got Your Back.