Chapter 14

Chapter 14 - Chapter 14- Organometallic Compounds I....

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Chapter 14 - Organometallic Compounds I. Organometallic Nomenclature a. Named as substituted derivatives of the metal i. Metal is parent ii. Attached alkyl group are given the appropriate prefix b. If the metal bears a non-carbon substituent, the substituent is considered to be an anion and named separately c. NaC-=CH is sodium acetylide II. Carbon-metal bonds a. Carbon is neither strongly electropositive or electronegative i. When bonded to an element more electronegative, C becomes polarized to be slightly positive ii. When bonded to an element less electronegative, such as a metal, C becomes polarized to be slightly negative b. Carbanion- an anion containing a negatively charged C i. Organometals have carbanion characteristics ii. As the metal becomes more electropositive, the ionic character of the C-metal bond becomes more pronounced. III. Preparation of Organolmetallic compounds with group I metals a. Organometals with group I metals are formed by a reaction of alkyl halide with the appropriate metal b. Alkyl Iodides are most reactive and Alkyl fluorides are fairly unreactive c. Organo(group I)metals are formed in hydrocarbon solvents. Diethyl Ether is most common i. Solvent must be anhydrous (no water) d. Mechanism i. Electron is transferred from metal to alkyl halide making the alkyl halide a negatively charged anion radical ii. Anion radical fragments to an alkyl radical and halide ion
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iii. The alkyl halide then rapidly combines with the metal atom to form the organometallic compound IV.Grignard Reagents- organomgnesium compounds a. Prepared from organic halides by reaction with magnesium to make an
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Chapter 14 - Chapter 14- Organometallic Compounds I....

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