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

Dihydroxylation

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

In this reaction, we learn how to use certain agents to add diols to a double bond. This is also known as the 1,2-syn diols reaction. 

Concept #1: General properties of syn vicinal dihydroxylation.

General Reaction:

You don’t need to know this entire mechanism, but I would suggest knowing the first step:

Example #1: Predict the product for the following multi-step reaction. 

Additional Problems
What is the major product of the reaction drawn below? For clarity, the other enantiomer was not drawn for those labeled as racemic.   
Suggest a synthetic scheme for the following transformation:
Give the product, or products, including stereochemistry of the reaction of (Z)-3-methyl-2-pentene with the reagent below. If the products are a pair of enantiomers, you need to draw only one and state that the other enantiomer is formed.  OsO4 / NaHSO3
Draw the organic product of the following reaction, being mindful of stereochemistry. If the reaction forms two enantiomers, draw one of the two enantiomers.
Consider the strucutres below and answer the following questions.  d. Which comopunds will each form a pair of enantiomers by reaction with OsO4 / NaHSO3 ?
What will be the major product of the following reaction? Pay careful attention to the stereochemistry of the product.
Which set of reagents could be used to effect this conversion?
Provide the major product for the alkene reaction below. 
Show the appropriate arrow pushing on the left side of the equation and write the structre after the first immediate step on the right side. (please re-write the reagent where necessary)
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 all answers in skeletal form. 
Predict the product of the reaction: 
Show the appropriate arrow-pushing on the left side of the equation, and show the result after the first immediate step on the right side of the equation. (re-write the reagent where necessary!)
Draw the major organic products for this reaction. Show stereochemistry in your structures. Do not include lone pairs. Then check the box to indicate the stereochemical relationship of the products
Draw the structural formula for all the alkenes with the indicated molecular formula that, without undergoing a rearrangement, produce the compounds shown as major products. 
Draw the structure resulting from a reaction of osmium tetroxide (OsO4) and hydrogen peroxide (H2O2) with the following alkene.
Draw the product that's formed when 1,2-dimethylcyclohexene reacts with KMnO4 in basic aqueous solution. Use the wedge-and-dash bonds to show the correct arrangement of the substituents in the product.
Draw the two products that are formed when the compound shown below reacts with KMnO4 in basic acidic aqueous solution.
Consider the following reactions. Indicate how many stereoisomers you expect to be formed in the reaction, and specify what kind of isomers you expect.
Draw the product that's formed when 1,2-dimethylcyclohexene reacts with KMnO4 in basic acidic solution.