Ch. 16 - Aldehydes and KetonesWorksheetSee all chapters
All Chapters
Ch.1 - Covalent Bonding and Shapes of Molecules
Ch.2 - Alkanes and Cycloalkanes
Ch.3 - Stereoisomerism and Chirality
Ch.4 - Acids and Bases
Ch.5 + 6 - Alkenes and Reactions of Alkenes
Ch.7 - Alkynes
Ch.8 - Haloalkanes, Halogenation and Radicals
Ch.9 - Nucleophilic Substitution (Part 1)
Ch.9 - b-Elimination (Part 2)
Ch.10 - Alcohols
Ch.11 - Ethers, Epoxides and Sulfides
Bonus Chapter: Synthesis
Ch. 12 - Infrared Spectroscopy
Ch. 13 - Nuclear Magnetic Resonance
Ch. 14 - Mass Spectrometry
Ch. 15 - An Introduction to Organometallic Compounds
Ch. 16 - Aldehydes and Ketones
Ch. 17 - Carboxylic Acids
Ch. 18 - Functional Derivatives of Carboxylic Acids
Ch. 19 - Enolate Anions and Enamines
Ch. 20 - Dienes, Conjugated Systems, and Pericyclic Reactions
Ch. 21 - Benzene and the Concept of Aromaticity
Ch. 22- Reactions of Benzene and Its Derivatives
Ch. 23 - Amines
Ch. 25 - Carbohydrates
Ch. 27 - Amino Acids and Proteins
Naming Aldehydes
Naming Ketones
Oxidizing and Reducing Agents
Nucleophilic Addition
Organometallics on Ketones
Wittig Reaction
Overview of Nucleophilic Addition of Solvents
Acetal Protecting Group
Imine vs Enamine
Addition of Amine Derivatives
Oxidation of Alcohols
Reductive Amination
Alkyne Hydration
Wolff Kishner Reduction
Tautomers of Dicarbonyl Compounds
Acid-Catalyzed Alpha-Halogentation
Base-Catalyzed Alpha-Halogentation
Haloform Reaction
Ketone and Aldehyde Synthesis Reactions
Additional Practice
Physical Properties of Ketones and Aldehydes
Multi-Functionalized Carbonyl Nomenclauture
Nucleophilic Addition Reactivity
Wittig Retrosynthesis
Horner–Wadsworth–Emmons Reaction
Synthesis Involving Acetals
Tollens’s Test
Catalytic Reduction of Carbonyls
Alkyne Hydroboration to Yield Aldehydes
Reduction of Carbonyls to Alkanes
Clemmensen vs Wolff-Kischner
Alpha-Carbon Racemization
Carbonyl Missing Reagent
Carbonyl Synthesis
Carbonyl Hydrolysis
Carbonyl Retrosynthesis
Additional Guides
Acetal and Hemiacetal
Johnny Betancourt

Enolates are anions at the the alpha position of carbonyl compounds like ketones and aldehydes. They can participate in many kinds of reactions including tautomerization, alkylation, acylation, condensation, etc. 

Enolate Formation

Enolate formation oxyanion and carbanion resonance structure contributorsEnolate formation, oxyanion and carbanion resonance structure contributorsEnolate anions are intermediates of base-catalyzed tautomerization (aka tautomerism). Carbonyls and enols (aka alkene-ols) are tautomers and exist in equilibrium 

Tautomerization-mechanismTautomerization mechanismReactions:

Alkylation and Acylation

Enolate alkylation and acylationEnolate alkylation and acylation Enolates can undergo alkylation and acylation reactions. In these, the carbanion acts as a nucleophile to attack an electrophile like an alkyl halide or acyl chloride. Acylation reactions form beta-dicarbonyls

Condensation Reactions

Enolates can also attack carbonyls directly through nucleophilic addition, and in this process larger molecules are formed. Condensation reactions like Aldol, Claisen, and Dieckmann

Claisen condensation mechanismClaisen condensation mechanism

Johnny Betancourt

Johnny got his start tutoring Organic in 2006 when he was a Teaching Assistant. He graduated in Chemistry from FIU and finished up his UF Doctor of Pharmacy last year. He now enjoys helping thousands of students crush mechanisms, while moonlighting as a clinical pharmacist on weekends.