Ch. 10 - Addition ReactionsWorksheetSee 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
Addition Reaction
Markovnikov
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration
Hydroboration
Hydrogenation
Halogenation
Halohydrin
Carbene
Epoxidation
Epoxide Reactions
Dihydroxylation
Ozonolysis
Ozonolysis Full Mechanism
Oxidative Cleavage
Alkyne Oxidative Cleavage
Alkyne Hydrohalogenation
Alkyne Halogenation
Alkyne Hydration
Alkyne Hydroboration
Additional Practice
Thermodynamics of Addition-Elimination Equilibria
Stereospecificity vs. Stereoselectivity
Sulfonation
Oxymercuration-Reduction Full Mechanism
Hydroboration-Oxidation Full Mechanism
Alkoxymercuation
Interhalogenation
Haloether Formation
Simmons-Smith Addition Mechanism
Regiospecificity of Acid-Catalyzed Ring Openings
Anti Vicinal Dihydroxylation
Ozonolysis Retrosynthesis
LiBr and Acetic Acid for Anti Vinyl Dihaldes
Addition Reagent Facts
Predicting Stereoisomers of Addition Reactions
Addition Missing Reagent
Addition Synthesis
Addition Texas Two-Step
Addition Retrosynthesis
Addition to Concave vs. Convex Rings

Ethers are generally unreactive. However, epoxides (3-membered cyclic ethers) are highly strained, so they are able to react with nucleophiles in ways a typical ether could not. Let’s take a look. 

Concept #1: Acid-Catalyzed Epoxide Ring-Opening      

Acid-catalyzed ring openings favor addition to the MOST substituted carbon (thermodynamic control)

  • Opening of 3-membered intermediates/molecules always results in anti-addition.

Concept #2: Base-Catalyzed Epoxide Ring-Opening      

Base-catalyzed ring openings favor addition to the LEAST substituted carbon (kinetic control). 

Additional Problems
What is the product, A, that would be obtained from the following reaction sequence?
Propose a reasonable mechanism for the following reaction.
Complete the following reaction supplying the missing product and showing correct regio- and stereochemistry where applicable. If a racemic or diastereomeric mixture forms show all stereoisomers; if no reaction takes place, write N.R.
Complete the following reaction with the correct structure of the product. Don’t forget to specify the stereochemistry.
Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw all answers in skeletal form.
Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw all answers in skeletal form.
Which one of these structures best explains the reason why epoxide  1 gives compound 2 instead of compound 3 upon reaction with HBr?
Determine the final product when the following undergoes acidic cleavage. 
Determine the final product when each of the following undergoes acidic cleavage.   
Propose a mechanism for the following reaction.   
Determine the final product when each of the following undergoes basic cleavage.  
Determine the final product when each of the following undergoes basic cleavage.
Predict the product of the following rxn:
Draw (with curved arrows) a plausible mechanism for the following transformation:
Write the mechanism and final product for the reaction of 1-propynyllithium with trans-1,2-dimethyloxacyclopropane. If a mechanism has more than one step, show each step separately. Show all charges and keep count of the electrons by the appropriate notation ("curved arrow" or "fishhook" notation).
What is the expected product of this reaction?
What is the principal product of this reaction?
Fill in the box with the appropriate reactant, reagent, or product. Some boxes require more than one step.
Supply the missing reagent(s) needed to complete the following synthetic transformation. Indicate only one step in the box, and assume aqueous work up where required.
Propose a mechanism for the following reaction.
What is the product when the follwing molecule is treated with catalytic sulfuric acid? Please provide the mechanism.
Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.
Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.
Draw the structure of the major chiral product, resulting from the following reaction. Assign R and S configuration to the chirality centers for that molecule.
Predict the product of the following reaction showing stereochemistry if applicable.
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product, if stereoisomers are produced in the reaction be sure to indicate the relationship between them. Draw the answer in skeletal form.
Propose a mechanism for the following reaction
Provide a mechanism for the following reaction. Be sure to include all intermediates, formal charges and arrows depicting electron movement.
Conider the sequence of reactions shown below. What is the structure of Compound X? Write your answer in the empty box below. Furthermore, propose a mechanism for the conversion of Compound Y into Compound Z under the reaction conditions indicated. Use normal curved arrows to show movement of electron pairs, and be sure to draw structures of all important reaction intermediates. If an intermediate is a resonance hybrid, it is only necessary to draw the MOST IMPORTANT contributing resonance structure. 
For the reaction below, draw the structure of the appropriate compound. Indicate stereochemistry where it is pertinent.
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate, if stereoisomers are produced draw one and state the relationship between the other stereoisomer formed. (enantiomers, diastereomers, etc.).
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate, if stereoisomers are produced draw one and state the relationship between the other stereoisomer formed. (enantiomers, diastereomers, etc.).
Predict the product:
Predict the product for the following transformations. When necessary please explicitly show the stereochemistry of the product.
Predict the product:
Based on the principles of acidic and basic cleavage as well as epoxidation, determine the necessary reagents for the each of the following transformations.
Provide the reagents to accomplish the following transformations. More than one step might be required for each transformation.
Supply the reagent(s):
Provide an organic reaction in which the given intermediate or transition-state structure is involved and give a chemical equation for your selected organic reaction that includes the following in each of your answers:(i) structural formula(s) for the organic reactant(s) [Be sure to show stereochemistry clearly when necessary.];(ii) a structural formula for the major organic product [Be sure to show stereochemistry clearly when necessary.];(iii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula for inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.) As we do for most organic reaction equations, the chemical equations that you give do not need to be balanced. Be sure to show stereochemistry clearly when necessary.
(a) Given the above sequence of reactions, draw structures for A through E.
(b) Rewrite the reaction sequence, showing all nonbonding electron pairs and using curved arrows to show electron pair movements.
Predict the product(s):
Provide the major organic product(s) of the following. 
Predict the principal organic product(s) of the following reaction. Specify stereochemistry as is appropriate.
Provide the major organic product(s) of the following. 
Predict the principal organic product of the following reaction. Specify stereochemistry where appropriate.
Will the nucleophile attack the least or the most substituted atom on the following epoxide when the nucleophile is ethyl amine? When the nucleophile is HCl?  
Draw the structural formula of the product of the reaction shown below. You do not have to consider stereochemistry.
Draw the structural formula of the product of the reaction shown below.  
Which of the followings reagents would be used to carry out the reaction shown below?
Give the product of the following reaction. 
Draw the structural formula of the product of the reaction shown below. You do not have to consider stereochemistry.
Draw the major product formed when the following epoxide reacts with aqueous acid. Use wedge/dash bonds, including H's at each stereogenic center, to show the stereochemistry of the product.
Draw the major product formed in the following reaction.
Which one of the following statements about Reaction 3 is correct? a. The major organic product(s) arise from nucleophilic attack at carbon E b. The major organic product(s) arise from nucleophilic attack at carbon F c. None of the above
Draw the structural formula of the product of the reaction shown below. You do not have to consider stereochemistry.