Grignard reaction: addition of phenylmagnesium bromide to ethyl-3oxobutanoate ethylene ketal

by: Sulaiman Nasser Alshidhani

Department of Chemistry, College of Science, Sultan Qaboos University, Muscat, Oman u081777@squ.edu.om
ABSTRACT

The aim of this project is to prepare 4,4-Diphenyl-but-3-en-2-one by addition of phenylmagnesium bromide to ethyl 3-oxobutaneoate ethylene ketal using Grignard reaction technique

Figure 1: reaction scheme The final product (4,4-Diphenyl-but-3-en-2-one) was 1.8649 g, yield = 74.82% INTRODUCTION Spectroscopic data for 4,4-Diphenyl-but-3-en-2-one

Grignard reagents are the most important organometallic reagents in organic chemistry which are an organomagnesium compounds. They are called after the French chemist Victor Grignard. For developing efficient methods for the preparation of organic derivatives of magnesium and explained their application in the synthesis of alcohols, Grignard awarded the 1912 Nobel Prize in Chemistry. Grignard reagents are prepared from organic halides by reaction with magnesium

Figure 1: Equation of Grignard reagent formation The Grignard reaction is an organometallic chemical reaction in which alkyl- or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in an aldehyde or ketone.

1H

NMR

Figure 2: Equation of Grignard reagent addition

In the Grignard reagent, the bonding electrons between carbon and magnesium are shifted away from the electropositive Mg to form a strongly polar covalent bond. As a result the charge distribution in the Grignard reagent is such that the organic group (R) is partially negative and the MgX group is partially positive. This charge distribution directs the manner in which Grignard reacts with other compounds. - + RMgX

13C

NMR

RESULTS & DISCUSSION

The Grignard reaction is very reactive. It must b`e used in a reaction as soon as it is created. Moisture must be avoided. Water acts as an Acid in this reaction; thus the acid proton competes for the Magnesium in an acid base reaction. Therefore, moisture could result in the formation of a Hydrocarbon R-H

Infrared Spectroscopy

Anhydrous Ether is used to stabilize the Grignard. Therefore, the reaction should take place in anhydrous condition. For part 1 the yield was 44.92% which is slightly low and the mainly due to the experiment conditions that is not 100% anhydrous condition. The melting point was in the range 92-94C. In part 2 of the experiment the percent yield was 74.88% which is very good. The spectroscopic data and melting point show that the experiment was successfully done and the aim was achieved.

CONCLUSION

In conclusion, the aim of experiment was successfully achieved. Grignard Reagents are difficult to isolate, but they can be stabilized briefly in Ether solution and then used in the preparation of other compounds. The Alkyl part of the Grignard reagent work as base, the carbon atom bears a formal negative charge. Especially useful in Nucleophilic Addition reactions of the Carbonyl group, which has electrophilic character where the positive charge of the carbonyl carbon atom is attractive to the Grignard Nucleophile. In Grignard reaction, it is important to exclude water and air, which rapidly destroy the reagent by protonolysis or oxidation. The spectroscopic data and melting point range confirm that the final product is the desired product.

REFERENCES 1. 2. 3. 4. 5. Herwood, L. M. Moody, C. J.; Percy, J. M. Experimental Organic Chemistry, 2nd Edition, Blackwell Science, Oxford, 1999 McMurry, J. Organic Chemistry, 7th Edition, USA: Thomson, Brooks/Cole, 2007. "GRIGNARD REAGENTS http://www.infoplease.com/encyclopedia/science/grignard-reagent.html (accessed in 26 April 2013). "Grignard reaction "http://faculty.chemeketa.edu/lemme/CH%20123/handouts/Grignard.pdf (accessed in 27 April 2013). "Phenylmagnesium bromide" http://en.wikipedia.org/wiki/Phenylmagnesium_bromide (accessed in 23 Dec 2011).