Ch. 19 - Aldehydes and Ketones: Nucleophilic AdditionWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Naming Aldehydes
Naming Ketones
Oxidizing and Reducing Agents
Oxidation of Alcohols
Alkyne Hydration
Nucleophilic Addition
Organometallics on Ketones
Overview of Nucleophilic Addition of Solvents
Acetal Protecting Group
Imine vs Enamine
Addition of Amine Derivatives
Wolff Kishner Reduction
Baeyer-Villiger Oxidation
Acid Chloride to Ketone
Nitrile to Ketone
Wittig Reaction
Ketone and Aldehyde Synthesis Reactions
Additional Practice
Physical Properties of Ketones and Aldehydes
Multi-Functionalized Carbonyl Nomenclauture
Catalytic Reduction of Carbonyls
Tollens’s Test
Fehling’s Test 
Alkyne Hydroboration to Yield Aldehydes
Nucleophilic Addition Reactivity
Strecker Synthesis
Synthesis Involving Acetals
Reduction of Carbonyls to Alkanes
Clemmensen vs Wolff-Kischner
Baeyer-Villiger Oxidation Synthesis
Weinreb Ketone Synthesis
Wittig Retrosynthesis
Horner–Wadsworth–Emmons Reaction
Carbonyl Missing Reagent
Carbonyl Hydrolysis
Carbonyl Synthesis
Carbonyl Retrosynthesis
Reactions of Ketenes
Ketene Synthesis
Additional Guides
Acetal and Hemiacetal

Concept #1: General Reactions

Concept #2: Imine Mechanism

Concept #3: Enamine Mechanism

Additional Problems
Write a detailed mechanism that explains the following reaction of 6 to furnish piperidine 7 and cyclohexanone 8. Show all intermediates! Transfer protons intramolecularly!
An iminium can be turned into an enamine in one step. Draw the mechanism of this below. Draw all the arrows to indicate movement of the all electrons, write all lone pairs, all formal charges, and all products.
Predict the product for the following reaction sequence.
Which carbonyl compounds cannot form an enamine with amine 1?
What product will result from the reaction shown? a. enamine b. imine c. hydroxylamine d. amino acid e. hydrazine
Draw the major organic product in the box provided. 
Indicate the order in which the intermediates would appear during the conversion of   1 into 2. 1) 1 → I → IV → II → 2 2) 1 → III → II → 2 3) 1 → V → III → I → IV → 2 4) 1 → V → III → II → 2 5) 1 → II → I → III → IV → 2  
Pick the corn chips scent.  
Provide a complete mechanism for the following transformation.
One of the following reactions are incorrect as written. Choose which reaction, A or B is incorrect and draw the correct product. Then fill in the 2 sentences below.    Reaction           is incorrect. The correct product should be a                      . Reaction           is correct because we formed a                     .   
The reaction of an amine with a carbonyl compound leads to an iminium ion, which can often convert into an imine or an enamine. Which combination below cannot form an enamine or an imine (i.e., must remain as an iminium ion)?
Which compound would react with  A to give product B?
What is the product of the following reaction?  
Provide the missing product. Show only one most preferred product. Consider only monosubstitution for EAS where appropriate.
Predict the product when cyclopentanecarbaldehyde reacts with phenylhydrazine (PhNHNH2) in the presence of an acid catalyst. 
Complete the following reaction by drawing the structure of the principal major product. Indicate relative stereochemistry where necessary. If there is no reaction, write NR.
What combination of reactants can be used to form the product shown?  
What combination of reactants can be used to form the product shown?
Complete the following reaction. Pay careful attention to the stereochemistry of the product.
Propose a synthetic pathway from the indicated starting material to the designated product
For the reaction below, draw the structure of the appropriate compound in the box provided. Indicate stereochemistry where it is pertinent.
Show your understanding of the following reaction by showing the mechanism and predicting the products.
Draw the organic products of the following reaction.
Click the "draw structure" button to launch the drawing utility. Draw the organic products formed in the following reaction.
Draw the structure(s) of the major organic product(s) of the following reaction.
Which of the following would give an enamine when reacted with acetone? 
Give the major product for the following reaction.
Choose the correct product for the reaction shown. 
What carbonyl compound and amine are formed by the hydrolysis for the compound below?
What is the product of the following reaction?  
Draw the organic products formed in the following reaction.
Draw the product of the following reaction.
Draw the product formed for the reaction of benzaldehyde with butylamine (butan-1-amine) in the presence of mild acid.
Draw the major product for each of the following reactions:
Draw the neutral organic product expected under these reaction conditions.  
Provide the major organic product(s) of the reaction below.