Synthesis of Triphenylmethanol

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Synthesis of Triphenylmethanol

By | April 2012
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Abstract
This report presents the synthesis of triphenylmethanol from magnesium, bromobenzene, and benzophenone. A reflux apparatus was used to carry out most of the experiment. A great deal of color changes were noted throughout this process.

Triphenylmethanol was successfully synthesized, as can be verified by the IR that was obtained. The melting point was found to be 98.30°C- 146.2°C and the percent yield of triphenylmethanol was calculated to be 61.2%. Introduction

One of the most useful reactions to organic chemists, are those which can form carbon-carbon bonds. The Grignard reaction is one method by which to so.
Discovered by Victor Grignard, who received the Nobel Prize for his discovery in 1912, “the Grignard reaction involves the nucleophilic addition of an organomagnesium complex to a carbonyl carbon, followed by acid work-up” (Lab Manual, 69). Through carefully deciding which carbonyl compound to use, it is possible, using the Grignard reaction, to synthesize a primary, secondary, or tertiary alcohol.

The reaction is first started by forming a “Grignard reagent,” also known as an organomagnesium compound (Vollhardt, 305). This reagent is easily formed by reacting a haloalkane with a metal (either lithium or magnesium) suspended in diethyl ether or tetrahydrofuran (THF) (Vollhardt, 304).

“Grignard reagents are rarely isolated,” after formation, they are usually used immediately in the desired reaction (Vollhardt, 305). Since Grignard reagents are sensitive to both air and moisture, “they must be prepared and handled under rigorously air- and water-free conditions” (Vollhardt, 305). Once formed, the reagent will act similar to a Lewis acid, and attach to molecules which are Lewis basic, or will be solvated by the unshared pairs of electrons on the solvent (diethyl ether or THF).

The Grignard reagent will also act as a strong base and strong nucleophile. The reagent will react with protons which are more acidic than those on alkenes and...
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