Grignard Reagent.pptx
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1) Organometallic compounds contain carbon-metal (C-M) bonds and include Grignard reagents (organomagnesium compounds) and organolithium compounds. 2) Grignard reagents and organolithium compounds are strong nucleophiles and bases due to the electropositive nature of magnesium and lithium. 3) Grignard reagents are prepared through the reaction of alkyl or aryl halides with magnesium in dry ether. They have many applications as nucleophiles in addition and substitution reactions.
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organomagnesium-compounds.ppt
The document discusses organomagnesium halides (Grignard reagents). It describes how Grignard reagents are useful synthetic intermediates for carbon-carbon bond formation and are sources of nucleophilic carbanions. It summarizes several reactions of Grignard reagents including additions to carbonyl compounds, substitutions of alkyl/alkenyl/aryl halides, synthesis of ethers, amines, aldehydes and more. It also discusses the mechanisms and applications of important Grignard reactions such as the Bouveault, Benary, Bodrous, Dzhemilev and Kulinkovich reactions.
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Grignard reagents are organomagnesium compounds formed by the reaction of an organic halide and magnesium. The reaction proceeds through single electron transfers where radicals are converted to carbanions. Grignard reagents are strong nucleophiles similar to organolithium reagents that can form new carbon-carbon bonds. They were analyzed by decomposing ethylmagnesium iodide with sulfuric acid and directing steam through the apparatus to drive off any ethane, proving it did not appreciably dissolve under experimental conditions.
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Grignard reagents are organometallic compounds that function as strong nucleophiles. They can react with organic halides under anhydrous conditions to form new carbon-carbon bonds. In the lab experiment, phenylmagnesium bromide reacted with methyl benzoate to produce triphenylmethanol. Precautions were taken to remove water since Grignard reagents react strongly with Lewis acids like water. The product was analyzed using melting point and IR spectroscopy to evaluate purity and identify functional groups. The absence of water allowed the Grignard reaction to successfully synthesize triphenylmethanol.
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organomagnesium-compounds.ppt
The document discusses organomagnesium halides (Grignard reagents). It describes how Grignard reagents are useful synthetic intermediates for carbon-carbon bond formation and are sources of nucleophilic carbanions. It summarizes several reactions of Grignard reagents including additions to carbonyl compounds, substitutions of alkyl/alkenyl/aryl halides, synthesis of ethers, amines, aldehydes and more. It also discusses the mechanisms and applications of important Grignard reactions such as the Bouveault, Benary, Bodrous, Dzhemilev and Kulinkovich reactions.
Grignard reagents
Grignard reagents are organomagnesium compounds formed by the reaction of an organic halide and magnesium. The reaction proceeds through single electron transfers where radicals are converted to carbanions. Grignard reagents are strong nucleophiles similar to organolithium reagents that can form new carbon-carbon bonds. They were analyzed by decomposing ethylmagnesium iodide with sulfuric acid and directing steam through the apparatus to drive off any ethane, proving it did not appreciably dissolve under experimental conditions.
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- 1. SHRI SHIVAJI EDUCATION SOCIETY AMRAVATI’S J.D.P.S.COLLEGE, DARYAPUR ORGANOMETALLIC COMPOUNDS Rahul G.Sawarkar M.Sc. GATE, SET. Assistant Professor J.D.P.S. Mahavidyalaya, Daryapur.
- 2. CONTENTS 1. Introduction 2. Reactivity 3. Organomagnesium Compound 4. Preparation of organomagnesium compound 5. Applications of organomagnesium compound 6. Orgnolithium compound 7. Preparation of organolithium compound 8. Application of organolithium compound 9. References
- 3. INTRODUCTION Organic cmpounds that contain C-M bonds are called Organometallic compounds. Represented by R-M. The nature of C-M bond. Ionic character of C-M bond. More will be the electropositive character of metal, higher will be the ionic character between C-M bonds.
- 4. Percent ionic character of some C-M bonds are in given table. C- M Bonds % Ionic Character 1. C-Li 60% 2. C-Mg 52% 3. C-Al 40% 4. C-Zn 38% 5. C-Pb 38% 6. C-Cd 32% 7. C-Sn 28% 8. C-Cu 28% 9. C-Hg 24%
- 5. REACTIVITY Reactivity of organometallic compound as nucleophile and as base depends mainly on electropositive character of metal. More will be the electropositve character higher will be the reactivity of compound. Organolithiun and organomagnesium compound have highest ionic character and behave as strong nucleophile.
- 6. RMgX and RLi are also strong bases. Reaction with proton acids: CH3 CH2-MgBr H-OH CH3 CH2 -H Mg2 + OH - Br - Weaker base Stronger base Weaker acid Stronger acid pKa 51 pKa 15.7 + + + - pKeq = -35 - + + +
- 7. ORGANOMAGNESIUM COMPOUND OR GRIGNARD REAGENT French Chemist Victor Grignard
- 9. PREPARATION OF GRIGNARD REAGENT Dry ether
- 12. APPLICATION OF GRIGNARD REAGENT 1)Quantitative determination of active hydrogen: base acid acid Dry ether CH3 CH2-MgBr H-OH CH3 CH2 -H Mg2 + OH - Br - Weaker base Stronger base Weaker acid Stronger acid pKa 51 pKa 15.7 + + + - pK - + + +
- 14. 3)OTHER APPLICATION OF GRIGNARD REAGENT
- 16. PREPARATION OF ORGANOLITHIUM REAGENT Dry ether Method 1:
- 17. Method 2: Halogen - Metal Exchange CH3CH2CH2CH2-Li + CH3I CH3 Li + CH3CH2CH2CH2I n-butyllithium methyllithium Dry ether
- 18. APPLICATIONS OF ORGRNOLITHIUM COMPOUND 1)Preparation of Alcohol from organolithium compound: R-CO-R + R-Li (R)2 -C-OH R1 ketone alcohol Dry ether
- 19. 2)IN THE SYNTHESIS OF GILMAN REAGENT Lithium diorganocopper reagents, known more commonly as Gilman reagents. 2 CH3 CH2 CH2 CH2 Li + CuI or THF diethyl ether ( CH3 CH2 CH2 CH2 ) 2 Cu- Li + + LiI Butyllithium Copper(I) iodide Lithium dibutylcopper (a Gilman reagent)
- 20. 3)INDUSTRIAL USE OF BUTYLLITHIUM: Butyllithium is use in polymerisation of isoprene which leads to synthetic rubber. Synthetic rubber
- 21. REFERENCES 1) Advanced Organic Chemistry- By Jerry, March 2) Organic Chemistry- By Solomon 3) Organic Synthesis- By Jaya Singh & Jagdamba Singh 4)Modern Methods of Organic synthesis-By W. Carruthers. 5)Textbook of Organic synthesis-By R. O. C. Norman N. J. M. Coxon. 6) Organic chemistry- ByJ. Clayden.
- 22. Thank You….