Ch. 10 - Addition ReactionsSee 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

Oxymercuration

See all sections
Sections
Addition Reaction
Markovnikov
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration
Hydroboration
Hydrogenation
Halogenation
Halohydrin
Carbene
Epoxidation
Epoxide Reactions
Dihydroxylation
Ozonolysis
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 Full Mechanism
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

This is the second of three ways to add alcohol to a double bond. It is similar to acid-catalyzed hydration in terms of products, but the mechanism is WAY different. 

Concept #1: General properties of oxymercuration-reduction.    

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

General Reaction:

Concept #2: A worked-example of the acid-catalyzed oxymercuration-reduction mechanism.  

1. Electrophilic Addition

2. Nucleophilic Substitution (SN2)

3. Reduction (demurcuration)

Practice: Predict the product of the following reaction.

Additional Problems
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.
Predict the starting material of the following reactions.
Complete the mechanism for the following reaction. Draw all the arrows to indicate movement of electrons, write all lone pairs, all formal charges, and all products for each step. In the dotted boxes write which mechanistic element is involved in each step. If a racemic mixture is formed in the final product, you must draw both enantiomers and write racemic.
Follows Markovnikov’s Rule a)    Hydrogen goes to the double bonded carbon with _______ hydrogens. ( ______ substituted alkene carbon)  b)    Hydroxide ion goes to the double bonded carbon with _______ hydrogens. ( ______ substituted alkene carbon). 
Consider the strucutres below and answer the following questions.  a. Which compound will form different products by oxymercuation and hydroboration? 
Consider the strucutres below and answer the following questions.  b. Which compound is most likely to form a secondary alcohol by oxymercuration, but a tertiary alcohol by hydration using aqueous sulfuric acid?
Draw the mechanism of the following reaction. If no reaction would occur, say so. Show stereochemistry where relevant. Show the intermediate between steps 1 and 2.   
 Oxymercuration of methylcyclopentene gives which of the following products?
Which alkene would be expected to give the following alcohol by oxymercuration– demercuration? 
Given that 2-methyl-1-pentene undergoes oxymercuration–demercuration approximately 35 times faster than 2-methyl-2-pentene, predict the major product from oxymercuration– demercuration of limonene.
Oxymercuration–demercuration of allyl alcohol gives 1,2-propanediol.  
What is the major product from this reaction?
Predict the product:  
Predict the product(s).
Predict the product:
Provide the missing reagent or product.
Predict the major products of the following reactions. Include appropriate stereochemistry in the product structures. 4-chlorocycloheptene + Hg(OAc)2 in CH3OH 
Predict the minor and major products for the following reaction. Hint the products are isomers and in equilibrium with each other 
Draw the major organic product for the following reaction.
What is the expected major product for the following reaction?