Lab 3_ Preparation of Aspirin (1)

Benzoic acid and water were added to the test tube labeled "b.a." After stirring the mixture, sodium hydroxide (NaOH) vas added until the solid disappeared. Finally, hydrochloric acid was added drop by drop until blue litmus paper turned red. The solid present in the test tube after the addition of HCI is most likely: benzoic acid benzyl acetate O benzyl chloride sodium benzoate

Match column A (common active ingredients of insect repellants) to column B (IUPAC names). Column A Column B 1. Citronellol and Geraniol a. 6 parts DMP, 2 parts Indalone, and 2 part of Rutgers 612 b. Six esters (pyrethrins) 2. DEET 3. DMP c. 1-piperidine carboxylic acid-2(2- 4. 6-2-2 hydroxyethyl)-1-methylpropyl ester d. 3-(N-acetyl-N-butyl) aminopropionic acid 5. Picaridin 6. Citriodiol ethyl ester 7. IR-3535 e. butyl-3,3- dihydro-2,2-dimethyl-4-oxo-2H- pyran-6-carboохуlate f. para-menthane-3,8-diol 8. Rutgers 612 9. Indalone g. dimethyl phthalate 10. Pyrethrum h. 2-ethyl-1,3-hexanediol i. 3,7-Dimethyloct-6-en-1-ol j. N, N-diethyl-m-toluamide

REAGENT AMOUNTS In this section, you must record the actual amounts and volumes of reagens use in the lab. 090 ml Volume of methyl benzoate: mmol Equivalent to a molar amount of: 30 1.0 ml Volume of concentrated Nitric acid (16 M = 16 mol/L): Equivalent to a molar amount of : mmol Volume of concentrated Sulfurie acid acid (18 M = 18 mol/L): 3.0 ml Equivalent to a molar amount of: mmol 0.90 mL IL =0.0009 L lo0omL

Question 1 You are employed as a co-op student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated and the residue will be tested for the drug. You find that methylphenidate is highly soluble in 2-methyltetrahydrofuran, a bio-renewable solvent. Draw the structure of 2-methyltetrahydrofuran and give two reasons why it is a good solvent choice for liquid-liquid extraction. (Please find the image attached below to help you with this question) Question 2 (cont. from scenario 1). Your colleague is helping you develop the urine test. They suggest that the urine should be adjusted to a pH above 7 before…

I was super excited to get into the lab and make compound B from Compound A. I refluxed compound A in water and crossed my fingers. Son of a .... it turned out I made Compound C. What kind of reaction was this? Should I have used NaOH in water instead? $=$ H₂O Br OH B НО. 88

Which of the following can inhibit nitrification? 1. Low HNO2 2. High NH3 3. High NH4+ 4. pH < 5 5. Low HCO3- 6. High HNO2 7. High NO2

EXTRACTION FLOW CHART Draw the appropriate chemical structure (acid, base, neutral, conjugate base, conjugate acid) in the appropriate box in the following flow chart. Copy this into your laboratory notebook as part of the prelab. Indicate if the compound is present in solution or as a solid. Diethyl Ether Solution H₂N- OH benzoic acid Lower Aqueous Layer 6 M NaOH OCH CH₂ 9-Fluorenone Ethyl 4-aminobenzoate (Benzocaine) 3 M HCI Upper Organic Layer 3 M NaOH Lower Aqueous Layer Upper Organic Layer 6 M HCI

2. Show a reaction sequence to convert oil of wintergreen (methyl salicylate) into Aspirin (acetyl salicylic acid). This is a two-step sequence. You must show the structures for the intermediate product and the final product, along with the reagents/reaction conditions. OH

Do not give handwriting solution.

Use the following reagent table for the reaction of: cyclohexanol + H2 SO4 → cyclohexene Chemical MW (g/mol). Density (g/mL) mmols used Amount used cyclohexanol 100.16 0.9624 1.50 mL Sulfuric Acid 98.08 1.83 1.00 mL cyclohexene 82.14 Based on your answers in the previous two questions, identify what the Limiting Reagent for the reaction is:

A student use the same protocol as in the lab manual to extract benzoic acid, phenol, and naphthalene. Below are the steps he took Step 1 - Dissolve all three in 15 ml ether and place in separatory funnel Step 2- Add 15 ml of sodium carbonate and mix well Step3 - Isolate the aqueous layer and Add hydrochloric acid, which resulted in a precipitate Step 4- Add 15 ml of sodium hydroxide to the ether layer and mix Step 5- Isolate the aqueous layer and add hydrochloric acid, which resulted in a precipitate. Step 6- dry the ether layer and collect the solid that is left

How do we know what 1.1 equivalents are? Would it be 1.1 mmol? Same with 1 equivalent, 2.5 equivalents

Make sure you label everything as labeled as asked and make sure you explain everything is asked step by step.

Another extraction procedure involves extracting the acid first. Fill in the following flowchart before the start of your lab session. Show the completed flowchart to the TA as you enter the lab; this is part of your writeup. Ether solution Ether layer Aqueous layer Aqueous layer OH Benzoic acid 1. Add 3 M HCI 2. Separate the layers Add 6 M NaOH H₂N- Ethyl 4-aminobenzoate 1. Add 3 M NaOH 2. Separate the layers Aqueous layer OCH₂CH3 Aqueous layer Add 6 M HCI

Consider the retrosynthetic sequence shown below. Part: 0/3 Part 1 of 3 OH Br ? Draw the structure of the intermediate compound in the retrosynthetic sequence. Click and drag to start drawing a structure. C™ X 1:0 OH $ tu

draw the reactions that you performed in this experiment. You will need to draw the starting materials (carboxylic acid, the alcohol and the catalyst), and the product(s). There should be 12 total reactions. i am so confused on what to draw

what is the product of the following reaction?

THIS CAN NOT BE HAND DRAWN!

4. Imagine you performed the following extraction steps on a solution of salicylic acid and (R)-carvone in ethyl acetate. Draw the structure of salicylic acid and (R)-carvone after each step and predict the layer (organic or aqueous) it will be found in. OH OH salicylic acid (R)-carvone a. The solution of salicylic acid and (R)-carvone in ethyl acetate is washed with water. b. The organic layer from part a is washed with aqueous sodium hydroxide. c. The aqueous layer from part b is neutralized by adding sulfuric acid. Then it is extracted with ethyl acetate.

Answer the following questions following a Solubility and recrystalization lab for organic chemisty.  1. In a solubility and recrystallization lab you are working with the following chemicals : solids (benzoic acid, acetanilide,naphthalene, and resorcinol) and three solvents (water, ethanol and petroleumether) discuss and rank the polarity of the solvents and the polarity of the compounds being investigated. 2. Briefly describe how a mixture of sand and benzoic acid (soluble in hotwater) could be separated to produce pure benzoic acid.

Synthesis of Acetylsalicylic acid:  (a) Place approx. 1.4 g (±0.01 g) of salicylic acid (Caution: this is a skin irritant) in a dry 100 mL conical flask. Record the exact mass to three decimal places.  (b) Add 3.3 mL of acetic anhydride (Caution: acetic anhydride is a severe eye irritant – avoid skin and eye contact) in such a way as to wash down any material adhering to the walls of the flask, and then add 1 drop of concentrated sulfuric acid (Caution: sulfuric acid causes severe skin burns).  (c) Heat flask for 15 min. on a steam bath and without allowing to cool, add 2 mL of water and allow the flask to stand at room temperature until crystallisation begins. The crystallisation can be hastened by occasionally scratching the walls of the flask at the surface of the solution with a glass stirring rod. When the crystals begin to appear, place the flask in an ice bath, add 10-15 mL of cold water and chill thoroughly until crystallisation is complete.  (d) Collect the product on a…

Salicylic Acid Test. Methyl alcohol with salicylic acid and concentrated sulfuric acid willgive methyl salicylate or oil of wintergreen, a compound with an odor of peppermint.In a test tube containing 0.2 gm of salicylic acid, add 1 ml. of concentrated sulfuric acid(CAUTION!). Introduce 1 ml. of methanol into the test tube. QUESTIONS:1. What will be the result? 2. To make the odor more pronounced, pour the contents of the tube into a smallbeaker containing 20 ml. of water. What is the reaction called?  3.

show-all-working-explaining-detailly-each-step Answer should be typewritten with a computer keyboard.

How can you monitor the progress of a Grignard reaction? O Use TLC to monitor the concentration of magnesium metal. O Titrate the reaction mixture with nitric acid. Use TLC to monitor the consumption of the carbonyl-containing compound. O Add water and see if the mixture reacts with it. Question 2 What should you avoid allowing into the reaction mixture when preparing and using a Grignard reagent? Omagnesium Owater O organic solvents Oorganohalides

Answer all three parts plz. You are starting with three aryl bromides. They undergo a typical grignard reaction with magnesium metal and anhydrous ether (diethyl ether). Dry ice is then added to it and it is then cooled. Draw and label the names of the aryl carboxylic acids that will form for each. Part a) 4-bromonitrobenzene Part b) 4-bromotoluene Part c) 2-bromotoluene

$4/34) 2. Reduction of ethyl acetoacetate with sodium borohydride (3:38-5:32). a. In setting up the reaction described in the video you add 0.127 mL of ethyl acetoacetate, 5 mL of ethanol and 74 mg of sodium borohydride. Question #1: Which compound is the limiting reagent in this reaction? Question #2: What is the theoretical yield in this reaction? Question #3: What is the % yield if you isolated 89 mg of product?

Phenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, Ka. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (p = 9.9) with that of: cyclohexanol (pk = 16.0) 3-fluorophenol (pK₁ = 9.3) 4-acetylphenol (pK, = 8.1)