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Siksha 'O' Anusandhan (Deemed to be University)

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Any way to summarize this is simple as possible?

The first consideration in purifying a solid by recrystallization is to find a suitable solvent. There are four important properties that you should look for in a good solvent for recrystallization.

1. The compound should be very soluble at the boiling point of the solvent and only sparingly soluble in the solvent at room temperature. This difference in solubility at hot versus cold temperatures is essential for the recrystallization process. If the compound is insoluble in the chosen solvent at high temperatures, then it will not dissolve. If the compound is very soluble in the solvent at room temperature, then getting the compound to crystallize in pure form from solution is difficult. For example, water is an excellent solvent for the recrystallization of benzoic acid. At 10°C only 2.1 g of benzoic acid dissolves in 1 liter of water, while at 95 °C the solubility is 68 g/L.

2. The unwanted impurities should be either very soluble in the solvent at room temperature or insoluble in the hot solvent. This way, after the impure solid is dissolved in the hot solvent, any undissolved impurities can be removed by filtration. After the solution cools and the desired compound crystallizes out, any remaining soluble impurities will remain dissolved in the solvent.

3. The solvent should not react with the compound being purified. The desired compound may be lost during recrystallization if the solvent reacts with the compound.

4. The solvent should be volatile enough to be easily removed from the solvent after the compound has crystallized. This allows for easy and rapid drying of the solid compound after it has been isolated from the solution.

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So, I did Triphenylmethanol and Benzoic Acid lab experiment. I started with 1.4918g. Mass after experiment was 0.168g. My melting point recorded was 105.2- 117.0.

After that, I did recrystallization by re-dissolving my crude product in warm water. After everything, I discovered my pure product to be 0.0162. My melting point was 96.5-104.9. 1. Why is my second melting point low?

2. Write a balanced equation for the reaction of benzoic acid with sodium hydroxide. Why do you need to extract the ether layer with sodium hydroxide?

3. A possible side reaction during this reaction is the reaction of the Grignard reagent and water. Write a balanced equation for this reaction.

4. Theoretical and percent yield

5. Mechanism of the reaction

this is the procedure......

Procedure (Preparing Grignard reagent):

A 20 mL round bottom flask, two 5 mL conical vials, a 50 mL Erlenmeyer flask, a Claisen head, a syringe, and a Pasteur pipet are all cleaned with acetone and oven-dried to remove all traces of water

A drying tube with anhydrous calcium chloride is prepared.

0.15 g of shiny magnesium turnings are placed in the round bottom flask along with a dry magnetic stir bar.

The apparatus is set up as shown in the text and sealed to keep out air.

20 mL of anhydrous diethyl ether is added to the Erlenmeyer flask and stoppered.

0.70 mL of bromobenzene is placed into a preweighed conical vial and reweighed to determine the mass.

4.0 mL of anhydrous ether is added to the same conical vial.

Once the bromobenzene dissolves, 0.8 mL of the solution is removed with a syringe and the vial capped.

The bromobenzene solution is added to the magnesium in the round bottom flask.

The flask is heated just above the hot plate to about 60°C, with gentle stirring.

Bubbles should be noticed coming from the metal surface, marking the start of the reaction.

If the reaction doesn’t start, a glass stirring rod is used to crush the magnesium against the bottom of the flask. This may be repeated as necessary.

If the reaction still doesn’t start, a small iodine crystal can be added to the flask and the reaction heated again.

When the reaction has started, the solution should turn brownish-gray and cloudy.

More of the bromobenzene is added slowly over about 15 minutes until it has all been added.

Procedure (Benzoic Acid):

The phenylmagnesium bromide is cooled to room temperature and quickly transferred to a beaker containing 4 g of crushed dry ice.

The flask is rinsed with 2-3 mL of anhydrous ether, which is then also added to the beaker.

The reaction allowed to stand, covered with a watch glass, until the dry ice has sublimed.

The Grignard addition compound will appear as a viscous glassy mass.

10 mL of 6M hydrochloric acid is added slowly to the beaker, while stirring.

If a solid is still present, a small amount of ether can be added.

If the solid will not dissolve in the ether, a small amount of 6M hydrochloric acid can be added.

As a last resort, water may be added to attempt to dissolve any remaining solid.

The contents of the beaker, except for any residual magnesium, are transferred to a separatory funnel using a Pasteur pipet.

The beaker is rinsed with ether, which is also pipetted into the funnel.

The lower aqueous layer in the funnel is removed and discarded.

4 mL of 5% sodium hydroxide solution is added to the funnel and shaken.

The layers are allowed to separate and the lower aqueous layer is removed and saved in a new beaker.

The remaining ether phase is shaken with a second 4 mL portion of 5% sodium hydroxide and the lower aqueous layer removed and combined with the first.

Repeat previous step again.

The combined extracts are heated with stirring, hot enough to boil for about 5 minutes.

The solution is cooled and 5 mL of 6M hydrochloric acid is added.

The solution is further cooled in an ice bath.

The solids of this crystallization are collected by vacuum filtration.

The solids are allowed to dry and weighed in order to be able to calculate percent yield.

This crude product is dissolved in a small amount of hot water and then allowed to cool slowly.

Once it reaches room temperature, the flask is placed in an ice bath to complete crystallization.

The solid is once more collected by vacuum filtration and allowed to dry completely.

If desired, the IR spectrum of the product can be completed.

Am talking about the second melting point. Thanks!

Answer: The lower melting point you observed during the recrystallization proc...
Answer: products in this experiment: Triphenylmethanol, hydrogen gas, and/or w...
Answer: bStep-by-step explanation:Answer: b) Water dissolves in acetone, so ri...
Answer: 1. Triphenylmethanol synthesis using the Grignard reaction must be anh...

1. The glassware that is to be used for a Grignard reaction is washed with water and acetone, and dried thoroughly before the reaction is to be performed. Select the most likely reason why.

a. Acetone is needed to react with the silanol groups on the surface of the glassware.

b. The acetone adheres to the sides of the glassware as it dries, and it catalyzes the formation of the Grignard reagent.

c. Grignard reactions are highly endothermic, and residual water will freeze during the reaction.

d. If the glassware is not completely dry, residual water or acetone will react with the Grignard reagent.

2. A Grignard reaction is to be performed in diethyl ether solvent. Select the appropriate grade of diethyl ether for a Grignard reaction.

a. anhydrous grade

b. spectroscopy grade

c. ACS grade

d. technial grade

3. Crude triphenylmethanol was recrystallized using a 2:1 mixture of hexane:ethanol. Select the most likely reason why this recrystallization solution was chosen over pure ethanol.

a. Formation of triphenylmethanol crystals in the presence of pure ethanol is rapid, resulting in lower purity.

b. Triphenylmethanol is very soluble in pure ethanol and its recovery during recrystallization would be low.

c. Hexane stabilizes the phenyl groups of triphenylmethanol, protecting it from decomposition in the presence of heat.

d. Triphenylmethanol is relatively insoluble in pure ethanol, and not enough of it would dissolve for a recrystallization.

4. Which of the following is NOT a reason why heating a reaction mixture directly on the surface of a hot plate can be problematic?

a. Hot plates can heat glassware unevenly, which can lead to stress and cracking.

b. It is difficult to measure and maintain the temperature of a reaction when using the common, traditional style of hot plate.

c. Flammable solvents with low boiling points may ignite.

d. Hot plates cannot heat above 200 °C.

5. A Grignard reaction is performed by heating phenylmagnesium bromide and benzophenone under reflux in diethyl ether. Given that diethyl ether boils at 35 °C and benzophenone boils at 305 °C, select the appropriate temperature for the reflux.

a. 35 C

b. 25 C

c. 305 C

d. 100 C

Answer: d c a b dStep-by-step explanation:1. Answer: d. If the glassware is no...
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