CHEM 344 - Lab Report #6-7
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Olivia Dobson CHEM 344-03 02/21/2023, 02/28/2023 Lab #6/7 Grignard Reaction: Synthesis of Triphenylmethanol Objectives: To prepare a Grignard reagent from bromobenzene and magnesium; To perform a reaction using strictly anhydrous conditions; To perform a reaction in situ to preserve the Grignard reagent formed in the previous reaction; To characterize a product using melting point determination, 1
H NMR spectroscopy, 13
C NMR spectroscopy, IR spectroscopy, and thin-layer chromatography.
Overall Reaction Mechanism *Note: the benzophenone can also be shown with a partial positive on the carbon and partial negative on the oxygen, as in post-lab question 2*
Stoichiometry – Reaction 1
Reaction 1 Compound Amount Molar Mass (g/mol) Density (g/mL) mmol Molar Equiv. Bromobenzene 0.75 mL 157.01 1.5 7.17 1.16 Magnesium 0.150 g 24.305 1.74 6.17 1 Limiting Reagent
: Magnesium Theoretical Yield
: 1.12g phenylmagnesium bromide Stoichiometric Calculations – Reaction 1 1.) mmol: Bromobenzene: 0.75𝑚𝐿 𝑥
1.5 𝑔
1 𝑚𝐿
𝑥
1 𝑚𝑜𝑙
157.01 𝑔
𝑥
1000 𝑚𝑚𝑜𝑙
1 𝑚𝑜𝑙
= 7.17 𝑚𝑚𝑜𝑙
Magnesium: 0.150𝑔 𝑥
1 𝑚𝑜𝑙
24.305 𝑔
𝑥
1000 𝑚𝑚𝑜𝑙
1 𝑚𝑜𝑙
= 6.17 𝑚𝑚𝑜𝑙
2.) Molar Equivalents: Bromobenzene: 7.17 𝑚𝑚𝑜𝑙 𝑏𝑟𝑜𝑚𝑜𝑏𝑒𝑛𝑧𝑒𝑛𝑒
6.17 𝑚𝑚𝑜𝑙 𝑚𝑎𝑔𝑛𝑒𝑠𝑖𝑢𝑚
= 1.16
3.) Theoretical Yield: 6.17 𝑚𝑚𝑜𝑙 𝑚𝑎𝑔𝑛𝑒𝑠𝑖𝑢𝑚 𝑥
1 𝑚𝑜𝑙
1000 𝑚𝑚𝑜𝑙
𝑥
1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
1 𝑚𝑜𝑙 𝑚𝑎𝑔𝑛𝑒𝑠𝑖𝑢𝑚
𝑥
181.31 𝑔 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
= 1.12𝑔 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
Stoichiometry – Reaction 2 Reaction 2 Compound Amount Molar Mass (g/mol) Density (g/mL) mmol Molar Equiv. Phenylmagnesium bromide 1.12 g 181.31 1.14 6.18 1.03 Benzophenone 1.094 g 182.217 1.11 6.004 1 Limiting Reagent:
Benzophenone Theoretical Yield:
1.56 g triphenylmethanol Stoichiometric Calculations – Reaction 2 1.) mmol Phenylmagnesium bromide: 1.12 𝑔 𝑥
1 𝑚𝑜𝑙
181.31 𝑔 𝑥
1000 𝑚𝑚𝑜𝑙
1 𝑚𝑜𝑙
= 6.18 𝑚𝑚𝑜𝑙
Benzophenone: 1.094 𝑔 𝑥
1 𝑚𝑜𝑙
182.217 𝑔
𝑥
1000 𝑚𝑚𝑜𝑙
1 𝑚𝑜𝑙
= 6.004 𝑚𝑚𝑜𝑙
2.) Molar Equivalents: 6.18 𝑚𝑚𝑜𝑙 𝑝ℎ𝑒𝑛𝑦𝑙𝑚𝑎𝑔𝑛𝑒𝑠𝑖𝑢𝑚 𝑏𝑟𝑜𝑚𝑖𝑑𝑒
6.004 𝑚𝑚𝑜𝑙 𝑏𝑒𝑛𝑧𝑜𝑝ℎ𝑒𝑛𝑜𝑛𝑒
= 1.03
3.) Theoretical Yield: 6.004 𝑚𝑚𝑜𝑙 𝑏𝑒𝑛𝑧𝑜𝑝ℎ𝑒𝑛𝑜𝑛𝑒 𝑥
1 𝑚𝑜𝑙
1000 𝑚𝑚𝑜𝑙
𝑥
1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
1 𝑚𝑜𝑙 𝑏𝑒𝑛𝑧𝑜𝑝ℎ𝑒𝑛𝑜𝑛𝑒
𝑥
260.33 𝑔 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
1 𝑚𝑜𝑙 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
= 1.56 𝑔 𝑝𝑟𝑜𝑑𝑢𝑐𝑡
Procedure Procedure Observations 1. The apparatus was set up in the following way: A Claisen head adapter was placed in a 10mL r.b. flask and clamped to the ring stand. A drying tube filled with cotton and CaCl
2
was attached to the Claisen head. A rubber septum was placed in the top of the Claisen head.
Glassware placed in the oven for ~10 minutes 2. 150mg of magnesium ribbon was weighed out. It was polished, cut into small pieces, and then quickly added to the reaction flask (reattaching the Claisen head after). The stirrer/hot plate was placed 2-3 inches below the r.b. flask.
0.150g magnesium strip obtained from TA
Cut into very small pieces 3. A dry centrifuge tube was obtained from the oven and allowed to cool. A calibrated Pasteur pipet from the oven was used to add 700
μ
L bromobenzene to the centrifuge tube. 3.0mL anhydrous ether was added using a provided syringe or a clean, dry Pasteur pipet. The vial was sealed with a rubber septum to prevent moisture from contaminating it.
~750
μ
L added with a calibrated Pasteur pipet
4. A clean, dry 1.0mL plastic syringe fitted with a metal needle was used to draw up 0.8mL bromobenzene solution. The syringe needle was inserted through the reaction apparatus’s rubber septum, and the bromobenzene was added to the magnesium turnings with gentle stirring. The solution was heated if it did not turn a brown/gray color and bubbles (indicating phenyl magnesium bromide formation). No additional bromobenzene solution was added until the reaction was started.
The reaction started rapidly – within a couple of minutes
The solution turned brown, and the magnesium looked darker
A small aliquot of the reaction solution was given to a lab table mate to jumpstart his reaction
No heating was required 5. If the reaction still was not started, the following methods were employed: a.) a crystal of iodine was added to the flask and then heated gently b.) the Claisen head was detached, and the mixture was ground against the glassware walls using a dry, flat-headed stir rod with gentle heating c.) s small aliquot of the reaction solution and a few Mg turnings were removed from the flask and placed in a dry test tube. A glass stir rod was used to grind the turnings. The solution/turnings were transferred back into the main vessel if the reaction started.
None of the mentioned techniques were needed
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- HO CI Br b. Fill in the reactants and reagents necessary to make each compound below. a. HO. abel Madc In U Synthesis. Give the reagents necessary for each step. A152 75 4167 Fisnerbran Iter Paper ualitative Cat. No.: 05 09-801A Porosity: Medium Flow Rate: Slow Dia.: 7.0 cm- Pk. of 100 cir Fisher Scientificarrow_forward27. Which of the following is the best method for preparing CH3Br? A) CH3OH + Br- B) CH3OH + HBr C)CH3OH + Br2 D) CH3OH + NaBr E) CH3OH + Br+ 28. When 1-pentanol is heated with HCl/ZnCl2, 1-chloropentane is the major organic product. This reaction proceeds through an is produced as a byproduct. mechanism, and A) SN1, H2O B) SN2, H2O C) SN1, H2 D) SN2, H2 E) E2, H2 29. What is the major product of the following reaction? CH3 CH37 A. E. C CH 3 OH CH 37 CHCH3 + HBr CH 37 CH3Br II C CHCH3 CH 3 CH 3 CH 3 C CH2CH3 CH2Br CH3 Br heat B. -CH2CH2CH3 CH 37 CH3 -CH2CH2 CH3 Br C. CH 37 CH 3 C -CHCH 3 Br CH3 D.arrow_forward27. Which of the following is the best method for preparing CH3Br? A) CH3OH + Br- B) CH3OH + HBr C)CH3OH + Br2 D) CH3OH + NaBr E) CH3OH + Br+ 28. When 1-pentanol is heated with HCl/ZnCl2, 1-chloropentane is the major organic product. This reaction proceeds through an is produced as a byproduct. mechanism, and A) SN1, H2O B) SN2, H2O C) SN1, H2 D) SN2, H2 E) E2, H2 29. What is the major product of the following reaction? CH3 CH37 A. E. C CH 3 OH CH 37 CH 37 CHCH3 + HBr CH 37 CH3Br | C -CHCH3 CH 3 CH 3 C--CH2CH3 CH2Br CH 3 Br heat B. -CH2CH2CH3 CH 37 CH3 C -CH2CH2 1 CH 3 Br C. CH 37 CH 3 C -CHCH 3 Br CH3 D.arrow_forward
- Review topics] [References) 1. CI NaOH NH2 NaCI H20 2. OH NAHCO3 12 H20 CO2 Nal a = Proton transfer d = Electrophilic addition g = SN1 Nucleophilic substitution b = Lewis acid/base c = Radical chain substitution e = El Elimination h = SN2 Nucleophilic substitution f= E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2. Retry Entire Group 9 more group attempts remaining nswerarrow_forwardment/takeCovalentActivity.do?locator-assignment-také 3 q M >11 F3 [Review Topics [References] Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. $ 4 Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4.2-propanol 5. cyclohexanol R F ♫x Submit Answer F4 CI E % 5 Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3. CH3 T G F5 A a. LiAlH4 b. H₂SO4 c. HCI d. HBr e. SOCI₂ Cengage Learning Cengage Technical Support 6 Retry Entire Group 8 more group attempts remaining 4) Y H Reagents Available f. PBr3 g. CrO₂ h. NaH F6 i. CH₂MgBr j. CH₂CH₂MgBr & 7 O U F7 * k. CH3CH₂CH₂MgBr I. C6H5MgBr (phenylmagnesium bromide) m. (CH3)2CHMgBr n. pyridinium chlorochromate (PCC) 8 PrtScn | F8 K 91°F Mostly sunny Home ( 9 F9 O ) End 0 E ^ F10 P L 니 Previous DA PgUp…arrow_forwardDraw the major organic product of the reaction of aniline with excess methyl iodide. Include any lone pairs of electrons and nonzero formal charges. Draw only one compound. Your product should contain a benzene ring. NH2 excess CH3I 1st attempt See Periodic Table O See Hint H + • SUBMIT ANSWE 13 OF 25 QUESTIONS COMPLETED 31-56a.jpeg chromosome.jpegarrow_forward
- PLEASE HELP SHOW STEP BY STEP ELECTRON FLOW MECHANISM FOR THE FLOWING REACTION STEREOSELECTIVE ALKENE SYNTHESIS BY THE HORNER-EMMONS REACTION H (EtO), PCH,Ph (EtO),PCH₂Ph cat. BuчN* Br 50% NaOH hexanes ?arrow_forward5 a) For each of the reactions below, describe a suitable reaction mechanism, stating the reaction conditions and naming the major productsi) Nitrobenzene and Chloromethaneft) 2-chloro-2-methyl propane and aqueous potassium hydroxide.iii) Propanone and hydrogen cyanide.iv) iodoethane and sodium hydroxide in ethanol.b) i) Discuss the bonding and extra.stability of benzene,ii) Using suitable examples, compare the reactivity of benzene and ethane,arrow_forwardContent 54°F Clear * X app.101edu.co Draw the major product of the substitution reaction shown below. Ignore any inorganic byproducts. F1 Aktiv Chemistry. @ 2 CH3CO2H Draw SN1 Product F2 # 3 DII X OSN2/SN1 Reactions Fl: X G Which alkyl bromide i X F3 $ ▬ F4 % 5 J F5 A 6 Question 8 of 22 â 6 F6 & G whats a stro 7 Please select a c F7 O PrtScn 8arrow_forward
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