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

This is the last of three ways to add alcohol to a double bond. This reaction creates alcohols that are much different from the first two methods, so pay attention to the differences!

Concept #1: General properties of hydroboration-oxidation.     

General Reaction:

Concept #2: A worked-example of the acid-catalyzed hydroboration-oxidation mechanism.     

1. Electrophilic Addition

2. Oxidation

Practice: Indentify the mechanism of reaction and predict the product.

Note: @ 3:40 there should be an OH group, not BH2. :)

Practice: Predict the product of the following reaction.

Additional Problems
Supply the missing inorganic reactant (reagent) or catalyst that is missing in the reaction given below.
Which of the following would be a reasonable synthesis of CH 3CH2CH2CH2OH?
Predict the product(s) or reagents of the following reactions.
Predict the product for the reaction below. 
Predict the starting material of the following reactions.
(a) Which primary alcohol of molecular formula C5H12O cannot be prepared from an alkene by hydroboration–oxidation? Why? 
Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. 
(b) Write equations describing the preparation of three isomeric primary alcohols of molecular formula C5H12O from alkenes. 
Fill in the box with the product of the following reaction of alkenes. Draw only the PREDOMINATE REGIOISOMER and indicate stereochemistry by drawing dashes and wedges where appropriate. When a racemic mixture is formed you must draw both enantiomers and write RACEMIC in the box. 
Complete the following reaction with the correct structure of the product. Don’t forget to specify the stereochemistry.
Draw the starting material that under the given reaction conditions, result in the following product.
All the following reactions have been reported in the chemical literature. Give the structure of the principal organic product in each case.
All the following reactions have been reported in the chemical literature. Give the structure of the principal organic product in each case.
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.  BH3, THF - H2O/H2O2, NaOH
Follows Anti-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).   
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (f) Diborane in diglyme, followed by basic hydrogen peroxide 
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms 
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following: (f) Diborane in diglyme, followed by basic hydrogen peroxide
In a hydroboration-oxidation reaction, a hydrogen and an alcohol are added where there once was a double bond. Describe the regio- and stereochemical relationship between the two. Vicinal and trans  Geminal and cis Vicinal and cis Vicinal and racemic
Determine the mechanism and predict the product of the reaction:  
Predict the major product of the reaction shown.
Write the structure of the major organic product formed in the reaction of 1-methylcyclohexene with each of the following: (f) Diborane in diglyme, followed by basic hydrogen peroxide
From among the same product choice as Problem 6.68, which one is the major product of the following reaction?  
Give all possible product/products and designate stereoselectivity &/or regioselectivity by using wedges and dashes.   
What will be the major product of the following reaction? Pay careful attention to the stereochemistry of the product.
For the transition state structure below, choose an organic reaction in which it is involved and give a chemical equation for your selected organic reaction that includes the following: (i) structural formula(s) for the organic reactant(s); be sure to show stereochemistry appropriately when necessary (ii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula or inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.) (iii) structural formula(s) for the major organic product(s); be sure to show stereochemistry appropriately when necessary. As we do for most organic reaction equations, the chemical equations that you give do not need to be balanced.
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.
Which of the following would be produced from the following reaction? a) 1 and 4 b) 1, 2, 3, and 4 c) 3 and 4 d) 2 and 3 e) 1 and 2
Predict the product(s).
On catalytic hydrogenation over a rhodium catalyst, the compound shown gave a mixture containing cis-1-tert-butyl-4-methylcyclohexane (88%) and trans-1-tert-butyl- 4-methylcyclohexane (12%). With this stereochemical result in mind, consider the reactions in (a) and (b).(b) What two products are formed in the hydroboration–oxidation of this compound? Which one do you think will predominate?
Predict the product:
What is the expected major product of the following reaction sequence?
The principal organic product of the following transformation is: Anti-Markovnikov  
Predict the major product(s) :
Major product of the following reaction is: 
Draw the structure of the product that is formed when the compound shown below is treated with the following reagents: 1) BH3, THF, 2) H2O2, HO- 
Draw the structure resulting from a reaction of: diborane (B2H6), followed by alkaline hydrogen peroxide (NaOH/H2O2) with the following alkene.
What is major product of the following reaction? 
Complete the reaction below.
Give the major product of the following reaction.  
Click the "draw structure" button to launch the drawing utility. Draw one of the products of the reaction below.
Draw the organic product structure formed by the following reaction sequence.
Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme: