Chapter 20 Notes - CHAPTER 20 Organometallics/Introduction...

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CHAPTER 20 20.1 Introduction The carbonyl group is present in aldehydes and ketones . An aldehyde has at least one hydrogen atom bonded to the carbonyl group. A ketone has two alkyl groups bonded to the carbonyl group. What is the hybridization, geometry and bond angle of the carbonyl carbon? The carbonyl group can be represented by two resonance structures. The carbonyl group in aldehydes and ketones undergo a general reaction called nucleophilic addition . The carbonyl group can also be present as part of a functional group with an electronegative atom bonded to the carbonyl group. Done by Dr. Felix N. Ngassa for Chemistry 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 1
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Functional groups that contain a carbonyl group with an electronegative atom or group bonded to the carbonyl are carboxylic acids , acid chlorides , acid anhydrides , esters , and amides . Carbonyl compounds that contain leaving groups (electronegative atom or group) undergo nucleophilic acyl substitution . 20.2 Relative Reactivity of Aldehydes and Ketones Aldehydes are more reactive than ketones towards nucleophilic attack for both steric and electronic reasons. What is the explanation? Done by Dr. Felix N. Ngassa for Chemistry 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 2
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20.3 Organometallic Reagents Organometallic reagents contain a carbon atom bonded to a metal. Because metals are more electropositive than carbon, carbon bears a partial negative charge. Because carbon bears a partial negative charge, organometallic reagents function as bases and nucleophiles . Organolithium reagents: Organomagnesium reagents (Grignard reagents): Organocopper reagents (Organocuprates or Gilman reagents): How do the polarities of the C-M bonds compare? We can also think of sodium acetylide as an
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This note was uploaded on 05/25/2011 for the course CHEMISTRY 242 taught by Professor Ngassa during the Spring '11 term at Grand Valley State University.

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Chapter 20 Notes - CHAPTER 20 Organometallics/Introduction...

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