theoretical yield of triphenylmethanol theoretical yield of triphenylmethanol

Since benzophenone has the fewest moles, it is the limiting reactant. performing the technique, but there are other factors that probably affected these findings as yield. pn - Ph Ph Ph TV Figure 10.2. Cengage Learning, pg 64- Well, it would mean that every molecule reacted correctly (i.e., no side products are formed) at every step and that no molecule was lost on the sides of the glassware. Mass of Benzophenone is 1.09 grams. Introduction The purpose of the experiment is to synthesize triphenylmethanol from bromobenzene and benzophenone. Find the theoretical yield. phenyl magnesium bromide through nucleophilic acyl addition mechanism. Let's say you are trying to synthesize acetone to use in the above reaction. How do you find the theoretical yield of a limiting reactant? magnesium bromide, and use it to synthesize the alcohol triphenylmethanol via Grignard reaction. 51.4 So, to stop you from wondering how to find theoretical yield, here is the theoretical yield formula: The number of moles of the limiting reagent in the reaction is equal to: Stoichiometry is defined as the number before the chemical formula in a balanced reaction. Determine the melting point (and range) of your purified product. Calculate the theoretical yield of triphenylmethanol for the overall conversion of bromobenzene to triphenylmethanol. Bromobenzene was first mixed with The theoretical yield for trans-9-(2-phenylethenyl)anthracene was 0.1562g; the actual yield was 0.088 grams making the percent yield 56%. To find the theoretical yield, you can follow the steps below: Check out 9 similar chemical reactions calculators , Identify the limiting reagent, which is the reagent with the. product. 10.75 & CzeHi6O We use cookies to ensure that we give you the best experience on our website. filtered using a Hirsch funnel under vacuum. IMPORTANT NOTE: Yields can only be found using the limiting reagent. 149-153 C 160-163 C. Any, Physical Data for Reagents and Instruments. 3.650 & C1pH16O First, all of the glassware was dried and cooled to room temperature, then 0 g of Mg and 10 mL The stoichiometry is needed to reflect the ratios of molecules that come together to form a product. Calculate the overall theoretical yield for your final product of next week, triphenylmethanol (mw = 260 g/mol). benzophenone: 2.0 mmol. Cap the 8 mL conical vial, place it inside of a 100 mL beaker, and carefully store the beaker in your locker until next week. Theoretical yield is what you calculate the yield will be using the balanced chemical reaction. Full calculation including limiting reagent and reaction scheme must be clearly shown. Spread the product on an 8 1/2 x 11 sheet of paper to dry. Chemistry 211 Experiment 2 MiraCosta College. Any leftover moisture and water was Add 0.5 cm of sand. need complete answer of the given questions.. as per the given info, CALCULATION: Calculate the theoretical yield of Triphenylmethanol. 6 mL of HCl was then added to the reaction mixture to one Erlenmeyer flask. Get 5 free video unlocks on our app with code GOMOBILE. The reagent was then mixed with a benzophenone ether solution to form a benzene Place the dry product in a properly labeled zip-lock bag and turn it in to your TA with your lab report. You can then multiply this number by the stoichiometry of the desired product to find the number of moles formed, then use this to derive the theoretical yield. . Grignard reagents are extremely sensitive to moisture, therefore it is imperative that all apparatus and glassware used for their preparation be as dry as possible. Instead, biphenyl is removed by washing the crude products with hex- anes, a nonpolar solvent. What type of reaction is the synthesis of triphenylmethanol? All theoretical molar ratios are 1:1. How do you find the theoretical yield of Triphenylmethanol? Anhydrous CaCl2 -Drying tube Claisen adapter Air condenser 8 mL conical vial o - Hot plate stirrer Hot plato stirer Figure 10.4. Comparing the actual yield (1 g) and the theoretical (1 g), the experimental yield is lower. Report the theoretical yield of trityl tetrafluoroborate. By reacting an organohalide (usually a bromide) with magnesium in ethereal solvent, carbon becomes a nucleophile. Calculate the limiting reactant (all molar ratios are 1:1). Nam lacinia pulvinar tortor nec f, facilisis. determined. signal at ~2 ppm. CalculatedTheoreticalYieldoftriphenylmethanol=. What is the enthalpy of solubility of benzoic acid in kJ? moles of bromobenzene = 0.0025 moles. Donec a, acinia pulvinar tortor nec facilisis. Stir at room temperature for 5 minutes and then warm to reflux for an additional 5 minutes. The IR spectrum was useful in confirming the identity, as well as purity of the synthesized Nice! So, #"Theoretical yield" = 0.013 cancel("mol PhCOH") ("260.3 g Ph"_3"COH")/(1 cancel("mol PhCOH")) = "3.4 g Ph"_3"COH"#, #"% yield" = "actual yield"/"theoretical yield" 100 % = (2.6 cancel("g"))/(3.4 cancel("g")) 100 % = 76 %#. Although the yield was We can once again use the mass=molecularweightmole\small\text{mass} = \text{molecular weight} \times \text{mole}mass=molecularweightmole equation to determine the theoretical mass of the product. magnesium and anhydrous ether in a flask. mole=mass/molecularweight\small\text{mole} = \text{mass} / \text{molecular weight}mole=mass/molecularweight, Let's find the moles of acetic acid: Solubility is a chemical property that is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. To calculate the of triphenylmethanol, you divide the actual yield by the theoretical yield and multiply by 100. The theoretical yield of triphenylmethanol is Let say the weight of triphenylmethanol was 0.060 g. moles of Mg = 0.002 moles. Click 'Join' if it's correct. harrison chang experiment informal report april 10, 2021 hc abstract the purpose of this. 10. We dont have your requested question, but here is a suggested video that might help. We haven't considered the stoichiometry. Correct any flaws, and repeat the melting point. groups. Stirring was continued until all of it reacted. The measurements you need are the mass of the reagents, their molecular weights, the stoichiometry of the reaction (found from the balanced equation), and the molecular weight of the desired product. intermediate. 2003-2023 Chegg Inc. All rights reserved. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. 13. 14. It is the maximum mass of product that the reagents can form, and you can compare your yield against it to see how successfully you carried out your reaction. The Grignard reagent was synthesized from bromobenzene and magnesium and then reacted with benzophenone to produce triphenylmethanol. Grignard reagents react rapidly with acidic hydrogen atoms in molecules such as alcohols and water. Is Corsair H100x compatible with LGA 1200? Now that we know the limiting reagent and its moles, we know how many moles of the product will form. It acts as an intermediate in the production of the commercially useful triarylmethane dyes. the Grignard reagent formation by protonation of the Grignard reagents nucleophilic carbon. Snapsolve any problem by taking a picture. Melting point range determination is largely dependent on the skill of the person Video Transcript. Compare the melting points of the pure product and the literature value for pure triphenylmethanol and comment on the final purity of your product (i.e. Actual yield is what you actually get in a chemical reaction. Cross), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Psychology (David G. Myers; C. Nathan DeWall), The Methodology of the Social Sciences (Max Weber), Give Me Liberty! When the ether is gone, slowly add 23 mL of hexanes to the round bottom flask and allow the mixture to cool gradually to room temperature. The bromobenzene and magnesium were mixed with anhydrous ether to form the Grignard reaction. combing 2)0,0 When the reaction starts, the solution will turn cloudy, then amber and boil spontaneously. Remove the spinvane and pipette the aqueous layer into a 4-inch test tube (ether is less dense than water). that influenced the determined melting point range. This To improve this reaction and the yield of the product, the magnesium could be cut up 1 Answer. > EXAMPLE Assume that, in a preparation of triphenylmethanol, you prepared phenylmagnesium bromide by reacting 2.1 mL of bromobenzene (density 1.50 g/mL) with 0.50 g of magnesium in anhydrous ether. The round bottom flask Diphenylmethanol may be prepared by a Grignard reaction between phenylmagnesium bromide and benzaldehyde. Since we will not isolate the Grignard reagent, use the assumption that all of the original alkyl halide was converted to Grignard reagent. 141.5 Support the bottom of the vial on a cork stopper and press f ly on the Mg turning clean, dry glass stirring rod repeatedly to expose fresh metal to induce the reaction. Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. Instead, a second Grignard nucleophile attacks the newly formed ketone carbonyl yielding the final alkoxide, IV). How do you find theoretical yield and percent yield? 184.24g/molDiphenylmethanol / Molar mass. slightly lower than perfect, it was an acceptable value and proved the efficiency of this synthesis Vigorous stirring of the reaction vial contents is essential. value. What is the purpose of Grignard synthesis of triphenylmethanol? This theoretical yield calculator will answer all the burning questions you have regarding how to calculate the theoretical yield, such as how to find theoretical yield as well as the theoretical yield definition and the theoretical yield formula. Full calculation including limiting reagent and reaction scheme must be clearly shown. The percent yield is determined by calculating the ratio of actual yield/theoretical yield. Prepare a short column of magnesium sulfate or sodium sulfate Figure 4.3) to effect drying of the ether layer as follows a. (0.894g)/ (80.9g/mol)=0.0110 moles Theoretical yield of triphenylmethanol bromide: (0.000768mol)x (1mol/1mol)= 0.000768 molFinal weight of triphenylmethanol bromide in moles: (0.129g)/ (323.23/mL)=0.000399 molPercent Yield: (0.000399mol)/ (0.000779mol)x100=51.2% SN1 Reactions 1 Timberlake SN1 Reactions 2 What is nationalism and nation-building all about? : an American History (Eric Foner), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. 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Triphenylmethane can be synthesized by FriedelCrafts reaction from benzene and chloroform with aluminium chloride catalyst: 3 C6H6 + CHCl3 Ph3CH + 3 HCl. Reaction Scheme: Data and Results: Theoretical Yield of Triphenylmethanol (mmoles limiting reagent) (MM of product) = (.74) (182.21) = .134g Observations:-Crude product was a white/yellow color-Purified product was a clear transparent solution-MP - 159.4-161.8 Calculations: 1) Yield of crude triphenylmethanol product after drying for one week . To calculate the percent yield of triphenylmethanol, you divide the actual yield by the theoretical yield and multiply by 100. It was important that water be excluded from the reaction, in order to prevent the formation of benzene. weight of methyl benzoate = density * volume = 1.09 g/mL * 0.125 = 0.13625 grams. Donec aliquet. (Given your 1. The amount of moles was then converted into grams to determine the theoretical yield, 0.125 g. The percent yield was then calculated by dividing the actual yield by the theoretical yield and multiplying the result by 100%. Data for the synthesis of triphenylmethanol using a Grignard reagent Product Yield (g) Yield (%) Experimental Melting Point Literature Melting Point Appearance Triphenylmethanol (Pure) 1.214g 35.05% 161.8C - 162.4C 162C White solid (Pavia 311) HNMR and IR Data Summary bromobenzene: 2.1 mmol Theoretical yield is calculated based on the stoichiometry of the chemical equation. Calculate the theoretical yield of triphenylmethanol (M.W. What is the theoretical yield of Diphenylmethanol? 97% of Numerade students report better grades. If both have the same amount of moles, you can use either. Transcribed Image Text: 3. taking the melting point, the product sample should be completely dry. 3,544 g Cwol/i6O Bromobenzene Want better grades, but cant afford to pay for Numerade? N, ur laoreet. I will meet him CS three. Why is biphenyl formed as a by product in a Grignard reaction? In other words, work with moles and then convert them to grams. The mass of the pre-weighed watch glass = 19.8550 g The mass of the watch glass the product - 19.9508 g The actual yield of the product = 0.0958 g The limiting reagent = Magnesium The theoretical yield. 1. What is meant by theoretical yield? Grignard experimental setup 2. So it turns out that the acetic acid is the limiting reagent! Actual # of mmol the benzene rings of the compound. Triphenylmethanol consists of an alcohol group and aromatic bending; according to the peaks in the IR spectrum, the product that was synthesized during the experiment possessed specific functional groups that are present in the structure of triphenylmethanol. was heated at about 35 degrees Celsius and stirred until the reaction began. The signal at ~7 ppm is a bit more cluttered and Other sources of error could also have been human. Calculated Theoretical Yield of triphenylmethanol = 0.110g benzophenone * mol * mol product * 260.33g = 0.157 g triphenylmethanol 182.21g mol reactant mol product Observations After having dried for one week, the crude product was yellow in color and mostly liquid. The exit of other the m sodium saccharin with connecting with. BACKGROUND AND THEORY The Grignard reaction was one of the first organometallic reactions discovered and is still one of the most useful synthetically. 2. Remember to hit refresh at the bottom of the calculator to reset it. 15.6 million more of sodium saccharin. To find the theoretical yield, you must find the number of moles present of the limiting reagent. Calculate the crude percentage yield of Triphenylmethanol. The triphenylmethanol reaction was a bit more tricky and only 24.7% was recovered, though what was recovered was seemingly very pure. With the aid of the Vant Hoff equation, the enthalpy of solution of benzoic acid at those temperatures was determined as 10.82 KJ. When a Grignard reagent reacts with water, a proton replaces the halogen, and the product is an alkane. Want better grades, but cant afford to pay for Numerade? It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. But wait! Enter your parent or guardians email address: Whoops, there might be a typo in your email. into smaller pieces to speed up the Grignard reaction. The presence of free radicals leads to the generation of biphe- nyl as a byproduct (Figure 10.3). Clamp the Pasteur pipette upright and pass the ether layer through the drying agent into a 10 mL round bottom flask. All this information is hidden in the moles, which can be derived from a solution's molarity or concentration (you can learn how to do so with our molarity calculator and concentration calculator). 410.2 2.21 grams The main goal of this experiment was to synthesize triphenylmethanol from phenylmagnesium Let's use the mass=molecularweightmole\small\text{mass} = \text{molecular weight}\cdot \text{mole}mass=molecularweightmole equation again: Let's rearrange the equation to find moles. The Grignard synthesis of triphenylmethanol. The toxicological properties of this material have not been fully investigated. If you continue to use this site we will assume that you are happy with it. served as the Grignard reagent and was then used in a reaction to add carbonyl and ketone Is there confession in the Armenian Church. Theoretical yield is calculated based on the stoichiometry of the chemical equation. If you have impurities, suggest what these impurities may be. Add magnesium and bromobenzene to a reaction vessel. moles of methyl benzoate = .13625/136.15 = 0.001 moles mmol Draw the methyl benzoate solution into a clean dry syringe. The particular ester (methyl or ethyl esters being the most common ones) does not affect the final product, as the alcohol group is lost during the reaction. Course Hero is not sponsored or endorsed by any college or university. Grignard . Explore over 16 million step-by-step answers from our library, dictum vitae odio. 1.04 Triphenylmethanol is prepared from benzophenone using a Grignard reagent e.g. 1| 1 moltriphenylmethanol 260| 1 moltrityltetrafluoroborate 1 moltriphenylmethanol | 330 1 moltrityltetrafluoroborate| Theoretical yield of trityl tetrafluoroborate = 1 g 4. The student then used. This data The product was then Not too bad, right? Table 1: Weight and Percent Yield of Triphenylmethanol, Initial Weight of (g) Theoretical Yield (g) Actual Yield (g) Percent Yield (%). Exp #7 (35 & 35A) Synthesis of Triphenylmethanol, Accessible at The NMR spectroscopy of the compound was taken removed through heating with a Bunsen burner. EXPERIMENTAL PROCEDURE All glassware used in a Grignard reaction must be scrupulously dried, Dry the long plassen in un at 110for at least 20 minute drinhos, Clasen adapter 8 ml. The collected solid is then dissolved in 1.0 mL of 1-propanol using heat and then is allowed to crystalize. Yield, melting point and appearance Table 1. c. Add 2 cm of Na,so d. Add 0.5 cm of sand. If you are uncertain which of your reagents are limiting, plug in your reagents one at a time, and whichever one gives you the lowest number of moles is the limiting reagent. 12. The theoretical yield is the amount of product that would be formed from a reaction if it was 100% efficient. Skip to document. Analysis of the experimental and theoretical yield revealed a percentage yield of 88% Comparing the actual yield (1 g) and the theoretical (1 g), the . Biphenyl formation as a byproduct in a Grignard reaction Nam risus ante, dapibus a molestie consequ, ce dui lectus, congue vel laoreet ac, dictum vitae odio. Pour all of the filtrate into the hazardous waste container. phenyl magnesium bromide through nucleophilic acyl addition mechanism. calculate theoretical yield of triphenylmethanol in mmol and in grams. bromide. In Figure 2b, the proton NMR shows a sharp and intense added (dropwise) into the reaction solution via syringe and needle. Stirring of the mixture was 17. can be washed more thoroughly with petroleum ether to remove more of the impurities. benzophenone 2.0 mmol, Required # of mmol Triphenylmethanol is used as a reagent in the research laboratory. literature value. Add 53 mg (2.2 mmol) of "shiny" magnesium turnings (Mg, Grignard grade). Assume that you prepared phenylmagnesium bromide by reacting 2.1 mL of bromobenzene (density 1.50 g/mL) with 0.50 g of magnesium in anhydrous ether. Get 5 free video unlocks on our app with code GOMOBILE. Nam risus an, trices ac magna. "Grignard Reaction" Preparation of Triphenylmethanol Br MgBr 1) 2 mg Ether 2) PhCOCH3 og uger OCH P Phph + CH30 Benzophenone, III II MgBr O MgBr 3) HCI 3) HCl PhIPh ph. b. How do you find theoretical yield and actual yield? Themeltingpointrangeofthefinal,purifiedproductwas155.1-157.6C. Yieldofcrudetriphenylmethanolafterdryingforoneweek:55mgproductobtained, Yieldofpurifiedtriphenylmethanolfromthetriturationstep:43mgpurified, %YieldofpurifiedtriphenylmethanolfortheGrignardreaction:43/55*100=78.2%. 15. Many commerciallyavailable stocks, Grignard reagents are strong nucleophiles and react readily with the electrophilic carbon atom of a wide range of carbonyl groups. May cause respiratory and digestive tract irritation. No, the limiting reactant is not the theoretical yield. Allow the water layer (in bottom) and the ether layer on top) to fully separate 3. We reviewed their content and use your feedback to keep the quality high. Weigh the dried crystals and take a melting point and decide for yourself whether you should recrystallize your triphenylmethanol from hot ethanol or not. Byproduct formation is increased by an increase in concentration of the starting alkyl halide solution. It is used in the preparation of triphenylmethane. What is the theoretical yield (in grams) and percent yield of your triphenylmethanol product in this experiment? Explanation: EXAMPLE Assume that you prepared phenylmagnesium bromide by reacting 2.1 mL of bromobenzene (density 1.50 g/mL) with 0.50 g of magnesium in anhydrous ether. This Grignard reaction was performed through the reaction between phenyl magnesium bromide and benzophenone, followed by an acid work-up. What responsibilities do technicians have? Many reactions done so far have consisted of combining compounds and the switching of substituent groups. Accessed on 04/13/21. The triphenylmethanol reaction was a bit more tricky and only 24.7% was recovered, though what was recovered was seemingly very pure. magnesium metal 2.0 mmol When magnesium is added to the bromobenzene in ether, a Grignard reagent is formed. Full calculation including limiting reagent and reaction scheme must be clearly shown. They are also highly basic and react even more rapidly with any, To reduce an ester functional group to an alcohol, which of the following reagent/solvent combinations would be the best choice? 136.15 Reacting to form triphenylmethanol (MW=260.33): 2.5 mL of bromobenzene (MW= 157.01, Density=1.491) 0.505g of solid magnesium (MW=24) 1.2g methylbenzoate (MW=136, Density=1.09) Stoichiometric ratios: Bromobenzene:Mg:Methylbenzoate:Triphenylmethanol = 2:1:1:1 My TA said it will be bromobenzene, but I can't justify it in my calculations. The second step in the Grignard reaction is much simpler mechanistically (Figure 10.2). Grignard reagents are the starting points for the syntheses of many alkanes, primary, secondary, and tertiary alcohols, alkenes, and carboxylic acids. reagent. The purpose of this lab was to study the process of a Grignard reaction through the examination 6. To calculate the percent yield of triphenylmethanol, you divide the actual yield by the theoretical yield and multiply by 100. From there, we can use the amount of the limiting reactant to calculate the theoretical yield of A l C l X 3 \ce{AlCl3} AlClX3. So the no of mol of Triphenylmethanol produce is =0.0428351083mol. triphenylmethanol CpH,co 260.339 glmol Also, a competing coupling reaction to form biphenyl is not a major concern. Heat the mixture until the magnesium is melted. 2.1 What is the product of a Grignard reaction? Pellentesque dapibus efficitur laoreet. There you go! Calculate the crude percentage yield of Triphenylmethanol. The benzoic acid reaction was straightforward and a 54.4% yield was recovered. Multiply by 100 to convert to a percentage. 392.52 Let's ignore the solvents underneath the arrow (they will both be present in excess and therefore will not be limiting reagents), but also the sodium cation of the sodium cyanide, as it is just a spectator ion. I think A) is X is more polar than 1:9 1. How do I know what version of Lync CU I have. Calculate the \% recovery of purified Triphenylmethanol (Show your calculation even your attempt for recrystallization is not successful). This signal is a singlet, which most likely represents the isolated hydrogen Since benzophenone has the fewest moles, it is the limiting reactant. This experiment successfully explored the process of synthesizing triphenylmethanol, and What is the theoretical yield of triphenylmethanol when 4.275 g of bromobenzene is reacted with 1.004 g of Magnesium and then 5.109 g benzophenone? This table shows the expected yield and actual yield of product, along with the calculated percent bcnzophenone CuHwO 182.224 gfmol 9. The total amount of mass from the triphenylmethanol was converted to moles by using the molar mass of the triphenylmethanol. What functional groups are in triphenylmethanol? Loss of the methoxide ion (II) generates intermediate ketone (benzophenone), (III) that is generally not isolable. anhydrous ether were added to a round 25 mL round bottom flask. Place a wad of cotton in a Pasteur pipette. If you continue to use this site we will assume that you are happy with it. Required mass (mg) = 260.3) c. She obtains 0.269 grams of the product. Fill in the quantities of reagents used in this experiment. mole=mass/molecularweight\small\text{mole} = \text{mass}/\text{molecular weight}mole=mass/molecularweight, Acetone has a molecular weight of 58g/mole58\ \text{g}/\text{mole}58g/mole, so: Theoretical yield calculations : Moles of Benzophenone : View the full answer Transcribed image text: CALCULATION: Calculate the theoretical yield of Triphenylmethanol. 8. The observed experimental melting point was also around 10 degrees lower than the literature synthesis reaction. Analysis of the experimental and theoretical yield revealed a percentage yield of 88% The molar mass of #"Ph"_3"COH"# is 260.3 g/mol. Introduction is your synthesized product pure or does it contain impurities?). transferred to two clean centrifuge tubes and centrifuged for 1-2 minutes to separate the aqueous and evaluated, which allowed us to study the applications of spectroscopy. Time for some examples. mole=5/58=0.862mol\small\text{mole} = 5 / 58 = 0.862\ \text{mol}mole=5/58=0.862mol, Cyanide has a molecular weight of 26g/mole26\ \text{g}/\text{mole}26g/mole, so: How to achieve 100% efficiency? The purpose of this experiment was to reduce the carbonyl-containing compound benzophenone to the alcohol compound trimethylmethanol. As bromobenzene is relatively inexpensive, phenyl mag- nesium bromide may be used economically in excess. Mole of triphenylmethanol=0.00598 mol Step 4: Next step is to calculate Theoretical yield Molar mass of triphenylmethanol=260.33 g/mol Mole of triphenylmethanol=0.00598 mol Mass of triphenylmethanol=molemolar mass Mass of triphenylmethanol=(0.00598260.33)=1.557 g Hence, theoretical yield=1.557 g Step 2: Calculation of percent yield The Grignard reagent reacts with the remaining unreacted alkyl halide to give the dimer, biphenyl.