CHEM 245 Lecture Notes - Lecture 3: Organic Compound, Infrared Spectroscopy, Bromobenzene

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8 Mar 2016

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Fall 2015: experiment 3-synthesis of triphenyl methanol (80) Report appearance (typed, on time, formatted, presentable, complete) Triphenyl methanol was produced using a grignard reagent. The grignard reagent was formed when magnesium was added to the bromobenzene in ether. 0. 83 grams of triphenyl methanol was collected with a percent yield of 80%. Bromobenzene was the limiting reagent in this synthesis because of the smaller molar quantity (0. 00401 moles bromobenzene). The melting point of the final product was 161 - 1630c. The purpose of this experiment was to form triphenyl methanol using a grignard reagent. Grignard reactant was produced from magnesium and bromobenzene that was then reacted to benzophenone. It was critical to keep the reaction dry to enable to grignard reagent to work properly. The melting point of the final product, triphenyl methanol, was measured. *literature melting points and boiling points were taken from jean-claude bradley open melting point dataset and oxford university chemical.

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Can someone please help me figure this out? We have to figure out an experiment to get at least 90% yield of compound B.

These are the topics covered that we can use to plan this experiment:

1) Basic Operations: Using a weighing balance; Separation, Density.
2)Separating the Components of Panacetin - Acid-Base Reactions, Stoichiometry Techniques: Separation, extractions
3) Identifying the Constituents of Panacetin: Key techniques: Recrystallization and Melting point
4)Synthesis of Salicylic acid . Key techniques: Reflux, Recrystallization, Melting point
5) Separation of Unknown by Chromatography-Concepts: Polarity, capillary action, Technique: Column and Thin layer chromatography
6)Dehydration of cyclohexanol to an cycloalkene. Key Concepts: Preparation, and Reactions Hydration, Halogenation & Hydro halogenation of Alkenes;
7)Polarimetric Analysis of Unknown Sugars. Key concepts: Stereochemistry Techniques: Optical rotation
8)Properties of organic compounds -Concepts: Solubility, Hydrogen bonding; Technique: Distillation
9)Preparation of 2-chloro-2-methylbutaneâAn Sn1 reaction - Key concepts: Nucleophilic Substitution reactions

I would like to know about the answers of these questions based on the experiment of synthesis in Organic Chemistry 1: CONVERSION OF 1-Butanol to 2-METHYLHEXENES

Equipment Materials

50.00 ml buret, 250.ml volumetric flask, 1.00 ml volumetric pipet 10.0 mL volumetric pipet, 25.00 mL volumetric pipet, pipettor, 250 mL Erlenmeyer flask, 10.0 mL graduated cylinder, several beakers, several watchglasses, unkown bleach solution, 10% potassium iodide solution, 2M hydrochloric acid solution, 0.150 M sodium thiosulfate solution, 1% starch solution.

Background information regarding this experiment is as follows:

An aqueous solution of sodium hypochlorite (NaOCI) is a clear, slightly yellow liquid, and is commonly known as bleach. Aside from its uses as a bleaching agent, sodium hypochlorite solutions are also used as sterlizing agents and in water treatment. Industrial uses include agricultural, food handling, paper production, and textile production. Sodium hypochlorite is also added to waste water to reduce odors.

The concentration of sodium hypochlorite in bleach solutions can be determined by titration. Therefore, we must use a two-step method to titrate sodium hypochlorite. In the first step, sodium hypochlortie, hydrochloric acid, iodide ion, and starch are combined to form a starch-triiodide complex. In this step there are 3 reactions that take place:

The result of these 3 reactions is that when sodium hypochlorite is present the starch-triiodide complex is produced.

In the second step the starch-triiodide product is titrated by sodium thiosulfate to form a colorless solution of iodide, dithionate.

I do not know how to answer the following on the data sheet: (? means I do not know how to answer)

Table 1:

Mass of 1.00 ml of unknown (by tare): 10.552 g

Density of bleach: (g/ml) : 1.055 g/ml

Volume of diluted bleach used in each titration: 10.00

Concentration of sodium thiosulfate: ? (M)

Titration Data:

Initial buret reading (ml): trial1: 0.000 ml Trial 2: 0.00 ml Trial 3: 0.000ml

Final buret reading (ml): trial 1: 13.50ml Trial 2: 13.30ml Trial 3: 13.40ml

Volume delivered(ml: trial 1: ? Trial 2: ? trial 3:?

Calculations: (show clearly)

For trial 1,2,3 ???

1.Moles of Na₂S₂O₃ in titration: ??? trial 1,2,3

2.Moles of NaOCl: ???trial 1, 2,3

3.Average moles of diluted NaOCl: (one answer) ?

4.Average moles of undiluted NaOCl: (one answer.. mol) ?

5.Standard Deviation: (one answer) (mol)

6.Average mass of NaOCl in 25.00mL of undiluted bleach: ? (g)

7.mass of 25.00 mL of undiluted bleach: ? (g)

8. Mass % of NaOCL from experiment: ? (%)

9.Actual mass % of NaOCL (from prof; student does not make an entry):? (%)

More questions all need to be answered please:

1. Calculate the volume of the reagent thiosulafte solution which would be required if you titrated a 25ml sample of the original commercial bleach instead of 25ml of the diluted solution.

2. Why would we choose a graduated cylinder to measure the HCl and KI solutions instead of a volumetric pipette? When would we use a volumetric pippette?

3. You calculated the mass percent of sodium hypochlorite in the bleach( dilute and undiluted). Now calculate the molarity of the sodium hypochlorite in the diulte and undiluted solution/

4. Use oxidation states to show that equations (2) and (4) in the introduction are redox reactions and that equation 1 is not a redox reaction. :

-(1) NaOCl(aq) + HCl(aq) yields HOCl(aq)+NaCl(aq)

-(2) HOCL (aq) + HCl(aq) + 3I(aq) yields I3(aq) + 2CL(aq) + H₂O(l)

-(4) (I₃) (Starch) + 2S₂O₃ yields 3I + S₄O₆ + starch

5. combine equation 1-3 to show the overall reaction for the products of the starch-triiodide complex.

-(1) NaOCl(aq) + HCl(aq) yields HOCl(aq)+NaCl(aq)

-(2) HOCL (aq) + HCl(aq) + 3I(aq) yields I3(aq) + 2CL(aq) + H₂O(l)

-(3) I₃ + Starch yields (I₃) (Starch)

6. What standard was used in this experiment?

7. Describe the naming of NaClO and HClO. What are the names of the following compounds? NaClO₂ , NaClO_3, NaClO₄ , HClO₂, HClO₃, HClO₄

8 Submit a one paged (typed double spaced) report that discusses the following topics:

a. the goals or objectives of the experiment

b.your results as they relate to the goals and objectives

c. the quality of your results.

CHEM 245 Lecture Notes - Lecture 3: Organic Compound, Infrared Spectroscopy, Bromobenzene

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