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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:
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 2
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
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 3
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
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 4
PRACTICE: Predict the product of the following reaction.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 5
PRACTICE: Predict the product of the following reaction.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 6
PRACTICE: Predict the product of the following reaction.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 7
PRACTICE: Predict the product of the following reaction.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 8
PRACTICE: Propose a synthesis to accomplish the following transformation.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 9
PRACTICE: Propose a synthesis to accomplish the following transformation.
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 10
PRACTICE: Propose a synthesis to accomplish the following transformation (Hint: 4 steps)
ORGANIC - BRUICE 8E
CH.11 - ORGANOMETALLICS
Page 11
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