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ORGANIC - BRUICE 8E

CH.11 - ORGANOMETALLICS

CONCEPT: NUCLEOPHILIC ADDITION

□ One of the most important ways that carbonyl compounds react is through nucleophilic addition.

● The carbonyl carbon is _____________________________

Nucleophilic Addition General Mechanism:

Nucleophilic Addition General Reactions:

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CH.11 - ORGANOMETALLICS

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CONCEPT: PREPARATION OF ORGANOMETALLICS

□ Organometallics are alkylating agents that have mostly group IA or group IIA metals bonded to a carbon structure

● They can also react as strong ____________. Beware of cross-reactions with acidic hydrogens.

1. Sodium Alkynides

2. Grignard Reagents

3. Organolithium Reagents

4. Gilman Reagents

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CH.11 - ORGANOMETALLICS

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CONCEPT: REACTIONS OF ORGANOMETALLICS

1. Substitution/Elimination on Alkyl Halides

2. Nucleophilic Addition on Ketones and Aldehydes

3. Nucleophilic Acyl Substitution on Esters

4. Base-Catalyzed Epoxide Ring Opening

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CH.11 - ORGANOMETALLICS

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PRACTICE: Predict the product of the following reaction.

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PRACTICE: Predict the product of the following reaction.

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CH.11 - ORGANOMETALLICS

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PRACTICE: Predict the product of the following reaction.

ORGANIC - BRUICE 8E

CH.11 - ORGANOMETALLICS

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PRACTICE: Predict the product of the following reaction.

ORGANIC - BRUICE 8E

CH.11 - ORGANOMETALLICS

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PRACTICE: Propose a synthesis to accomplish the following transformation.

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CH.11 - ORGANOMETALLICS

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PRACTICE: Propose a synthesis to accomplish the following transformation.

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CH.11 - ORGANOMETALLICS

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PRACTICE: Propose a synthesis to accomplish the following transformation (Hint: 4 steps)

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