write equations for the three reaction steps in the synthesis of triphenylmethanol:


This reaction produces the alcohol, triphenylmethanol in this case, and water soluble magnesium salts: A side-reaction can occur between phenylmagnesium bromide and …

x�b```f``����@����9L``P�d��q����v���������. The melting point of the final pure product was determined to be 160 – 163.2 centigrade and the product showed IR peaks at 3471.83 cm– and 3059.52 cm–. Reaction mixture was heated above a 60 centigrade hot plate. Thus, it is necessary to apply an extended amount of precaution and effectively keep the reaction free of water; this will most likely result in an increased yield of product and increased accuracy in results. H��H,*Q����u�tQ0P��srq��*��H-JN-()M�Q(��234�(�[���\.
Step 6:  Use a spatula to add a small piece of iodine crystal through the opening labeled “cap A” on the apparatus. Step 6:  Observe the evolution of the H2 gas during the reaction and then remove the reaction mixture from the ice water bath. Write equations for the three reaction steps in the synthesis of triphenylmethanol: (c) hydrolysis of the adduct of the Grignard reagent and benzophenone Expert Answer

Step 3:  Use forceps or tweezers to remove the spin vane from the round-bottom flask and place the spin vane into the 5 mL conical vial carefully, avoiding excessive splashing or loss of solution.

.777 g benzophenone * (1 mol/ 157.0 g)*(260.3 g/ mol triphenylmethanol) = 1.28 g, IR peaks of pure = 3471.83 cm– and 3059.52 cm–. © 2003-2020 Chegg Inc. All rights reserved.

The melting point of the resulting product of the Grignard reaction allowed the purity of the product to be evaluated. Background In 1912 Victor Grignard received the Nobel prize in chemistry for his work on the reaction that bears his name, a carbon-carbon bond-forming reaction by which almost any alcohol may be formed from appropriate alkyl halides and carbonyl compounds.
Teixeira, Jennifer M., et al. Isolation and characterization of the product-Triphenylmethanol via extraction: Step 1:  Using a clean filter-tip pipette, transfer the biphasic mixture from the round-bottom flask to a clean, dry 5 mL conical vial.

The final step of the synthesis is the hydrolysis of the magnesium alkoxide by a mineral acid. Why?

0000001261 00000 n Using this Grignard reagent, triphenylmethanol can be synthesized in a two-step reaction first adding the reagent and then adding an acid. In this case the acidic hydrogen is most likely water.

Ether was added to reaction mixture to replace what was lost during reflux.

The IR spectrum showed specific peaks at 3473.99 cm-1 which indicated the presence of alcohol, 3060.58 cm-1 which represented a carbon to hydrogen stretch, 1959.21 cm-1 which represented a carbon to carbon stretch, and 1596.90 cm-1 which represented a carbon to carbon stretch and was also indicative of aromatic bending.

“The question-driven laboratory exercise: a new pedagogy applied to a green modification of Grignard reagent formation and reaction.” Journal of Chemical Education 87.7 (2010): 714-716. H��S]k�0}�?�G�Ja��l �5ocҦ���b�ud�w��ҕ��� �����sOb��� �a6�K��h4N'���4�(Ԛ�B���% Ĝc�@o��]z�W䁯_,(�L�NO}���B��'��s�NТXb�@J��pC`B��!��! reaction steps in the synthesis of triphenylmethanol: 1. Aqueous layer was re extracted in the funnel.

Step 2:   Label two clean, dry 3 mL conical vials “vial #1” and “vial #2”.

Step 2:  Reflux the solution for an additional 30 minutes.

In the event that water was able to settle along the apparatus, the yield of triphenylmethanol available after the completion of the Grignard reaction was probably less than expected. <>>> <> Reaction mixture stirred until Grignard adduct was fully formed. Step 2:  Rinse the round-bottom flask with a small amount of diethyl ether.

3.1 mL petroleum ether (at 50 centigrade) added to oily solution. Due to the increase of the size of a molecule upon descending down the periodic table, it was evident that phenylmagnesium bromide was a good leaving. Percent yield was low however.

The use of Grignard reagents to produce compounds such as triphenylmethanol has been found to be not only a useful method of synthesizing an extended variety of functional groups but also to be a versatile technique. Step 3:  While keeping the round-bottom flask capped and sealed, allow the solution to cool to room temperature using an ice water bath. 1 0 obj Join our weekly lab-report contest for a chance to win cool prizes! & Free Chemical Reactions calculator - Calculate chemical reactions step-by-step This website uses cookies to ensure you get the best experience. As the result, the reaction synthesizes an alcohol, triphenylmethanol and magnesium salt (water soluble). Repeat the rinsing process if necessary. Step 13:  Calculate the percent yield of the product. Notice that you will need to include equations 2 and 3 multiplied by a factor of 2 to properly cancel the intermediate formed in step 1. Additionally, the IR peaks present in the IR spectrum of the product allowed the functional groups of the triphenylmethanol to be observed.

Yet, in order to explore the method in which phenylmagnesium bromide and methyl benzoate can react to produce triphenylmethanol, the Grignard reaction was utilized during this experiment. Step 1:  Before beginning the experiment, wrap the glassware involved in aluminum foil and place the glassware in an oven to ensure that the glassware is dry and free of water.

Notably, the absence of water during the Grignard reaction allowed for the product of the reaction, triphenylmethanol, to be synthesized successfully. Using the characterization techniques of IR and melting point it was determined that triphenylmethanol was synthesized.

endstream endobj 44 0 obj <> endobj 45 0 obj <>/Encoding<>>>>> endobj 46 0 obj <> endobj 47 0 obj <>/ProcSet[/PDF/Text]/ExtGState<>>> endobj 48 0 obj <> endobj 49 0 obj <>stream Step 4:  Place the round-bottom flask into a fume hood and carefully remove “cap A.”. 0 answer! Explain these results. Step 7:  Disassemble the microscale apparatus. The product will be characterized using melting point (comparing it to a standard of 162 centigrade) and IR (with standard peaks being broad at around 3600- 3200 cm– and sharp at 3100-3000 cm–. Gently shake the mixture. Using the Grignard Reaction to Prepare Triphenylmethanol

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