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
Sections
Naming Aldehydes
Naming Ketones
Oxidizing and Reducing Agents
Oxidation of Alcohols
Ozonolysis
DIBAL
Alkyne Hydration
Nucleophilic Addition
Cyanohydrin
Organometallics on Ketones
Overview of Nucleophilic Addition of Solvents
Hydrates
Hemiacetal
Acetal
Acetal Protecting Group
Thioacetal
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 Mechanism

Practice: Provide the chemical steps necessary for the following synthesis.

Practice: Provide the chemical steps necessary for the following synthesis.

Practice: Determine the starting materials based on the acetal group present.

Additional Problems
Complete the mechanism for the following acetal formation reaction. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. Remember, I said all the products for each step. IF A NEW CHIRAL CENTER IS CREATED MARK IT WITH AN ASTERISK AND WRITE RACEMIC IF APPROPRIATE . Do not draw arrows to indicate how one contributing structure relates to the other.
Draw the mechanism for the following reaction. Draw all the arrows to indicate movement of the all electrons, write all lone pairs, all formal charges, and all products for each step.
Draw the structural formula of the major organic product(s) in the boxes provided for the following reaction.
Predict the major product for the following reaction paying attention to the regio- and stereochemistry.
Which of the following is an acetal?
Suggest a reasonable mechanism for the following spirocyclic acetal formation. Use curved arrows to show electron flow.
Provide a detailed reaction mechanism for the following transformation.
Consider the three constitutional isomers of dioxane (C 4H8O2), shown below. One of these constitutional isomers is stable under basic conditions, as well as mildly acidic conditions, and is therefore used as a common solvent. Another isomer is stable under basic conditions, but undergoes hydrolysis under mildly acidic conditions. The remaining isomer is extremely unstable and potentially explosive. Identify each isomer and carefully explain the properties of each compound.
The compound shown below is a wasp pheromone. Draw the major product formed when this compound is hydrolyzed in aqueous acid. 
Propose a detailed mechanism for the following transformations. Show all possible resonance forms that contribute to this reaction pathway.
Draw the product of the reaction of 3-heptanone and two equivalents of 2-propanol.  
Which of the following compounds is an acetal? A) I B) II C) III D) IV E) None of these
Which is the main product that can be isolated from the reaction shown?  
Predict the major product(s) in the following reaction.
Predict the major product for the following reaction, paying attention to the regio- and stereochemistry where appropriate. 
Which acetal is derived from a ketone?
Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. 
Provide the missing product. Show only one most preferred product. Consider only monosubstitution for EAS where appropriate.
The product from the reaction of 4-methyl-2-pentanone and excess methanol with H2SO4 as a catalyst would be 
What is the product of the reaction shown below (Hint: hydrate formation under acidic conditions)?
Propose an electron push mechanism for the following transformation. Be sure to use the correct arrow formalism and correct formal charges
What products result from treating the compound shown with aqueous acid? (a) Acetone and 1,3-propanediol (b) Propanedial and 2-propanol (c) Propanedial and 2,2-propanediol (e) None of the above
What is the product of the following reaction?
List the following six mechanistic terms (nucleophilic addition, deprotonation, protonation, proton transfer, dehydration, nucleophilic addition) in order of the correct mechanistic sequence in the six step conversion of cyclopentanone to 1,4-dioxaspiro[4.4]nonane as shown below. 
What is the product of the following reaction?
Provide the mechanism for the conversion of  A to B.
Predict the product(s) in the following reaction. If more than one product is possible, then indicate the major product.
List the following six mechanistic terms (nucleophilic addition, deprotonation, protonation, proton transfer, dehydration, nucleophilic addition) in order of the correct mechanistic sequence in the six step conversion of acetone to 2,2-diethoxypropane as shown below.
In the following ketal formation reaction, the electrophile and nucleophiles are all contained within the same starting molecule. Provide a complete mechanism for this transformation.
Draw the structure(s) of the major organic product(s) of the following reaction.You do not have to consider stereochemistry.If a compound is formed more than once, add another sketcher and draw it again.Draw one structure per sketcher.Add additional sketchers using the drop-down men corner.Separate multiple products using the + sign from the drop-down menu.
Draw the product of the following reaction.
Draw the product of the following reaction.
For the reaction below:
Draw the product of the following reaction.
Draw the product of the following reaction.  
Draw the product of the following reaction.