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Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 16

Chapter 16: Aldehydes and Ketones


Table of Contents:

  1. Structure and Bonding

  2. Nomenclature

  3. Physical Properties

  4. Reaction Themes

  5. Addition of Carbon Nucleophiles

  6. The Wittig Reaction

  7. Addition of Oxygen Nucleophiles

  8. Addition of Nitrogen Nucleophiles

  9. Keto-Enol Tautomerism

  10. Oxidation

  11. Reduction

  12. Reactions at an α-Carbon



Structure and Bonding


Nomenclature


Aldehydes:

  1. Find the longest continuous carbon chain that contains the aldehyde and number from the carbon with the aldehyde group

  2. End the name in "al"


Ketones:

  1. Find the longest continuous carbon chain that contains the ketone group and number from the carbon closest to the ketone functional group.

  2. End the name in "one" and specify the number of the carbon to which =O is attached.



Physical Properties

Due to the =O, aldehydes and ketones are polar molecules. The carbon with =O is a Lewis acid (can be attacked) and the O is the lewis base (can attack).


Reaction Themes

Carbonyl reactions can happen in acidic and in basic conditions


Addition of Carbon Nucleophiles


1. Addition of Grignard Reagents


Addition of Grignard Reagents to ketones and aldehydes
Addition of Grignard Reagents to ketones and aldehydes

Mechanism Of Grignard Addition to the Carbonyls


Mechanism Of Grignard Addition to the Carbonyls
Mechanism Of Grignard Addition to the Carbonyls

How to predict the reactants of ketone/aldehyde +RMgBr when product is given?


Mayya's Trick

  1. Break between carbon with OH and its neighboring C

  2. Turn OH into =O and add MgBr (or Li) to the carbon broken off


How to predict the reactants of ketone/aldehyde +RMgBr when product is given?
How to predict the reactants of ketone/aldehyde +RMgBr when product is given?

2. Addition of Anions of Terminal Alkynes


Addition of Anions of Terminal Alkynes to ketones of aldehyde
Addition of Anions of Terminal Alkynes to ketones of aldehyde

Mechanism


Note: Once alkyne is attached, we can do alkyne reactions on it to produce

other groups.


3. Addition of Hydrogen Cyanide


Addition of Hydrogen Cyanide to a ketone or aldehyde
Addition of Hydrogen Cyanide to a ketone or aldehyde


The Wittig Reaction


Witting reaction converts carbonyls (ketones or aldehydes ) into alkenes (C=C).


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