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
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 an indentical mechanism to halogention, except with water as the nucleophile in the second step. Why would water prefer to react as a nucleophile over a halogen anion? Let’s find out. 

Concept #1: General properties of halohydrin formation.      

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

General Reaction:

Concept #2: A worked-example of the halohydrin mechanism.     

1. Electrophilic Addition

2. Nucleophilic Substitution (SN2) and Deprotonation

Practice: Predict the product of the following reaciton. 

Practice: Predict the products of the following reaction.

Additional Problems
Provide the major product for each of the following alkene reactions. 
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.
Read these directions carefully. Read these directions carefully. (It was worth repeating) For the reaction of an alkene with water in the presence of Cl2 shown below, fill in the details of the mechanism. Draw the appropriate chemical structures and use an arrow to show how pairs of electrons are moved to make and break bonds during the reaction. For this question, you must draw all molecules produced in each step (yes, these equations need to be balanced!). Finally, fill in the boxes adjacent to the arrows with the type of step involved, such as "Make a bond" or Take a proton away". MAKE SURE TO NOTICE THE QUESTIONS AT THE BOTTOM. If an intermediate or product is chiral, you only need to draw one enantiomer for this problem. For the product, you must draw both enantiomers and write "racemic" if appropriate. During the reaction described by the above mechanism, say what happens to the pH of the solution _________________________________________________________________________________ Is this reaction catalytic in acid? ____________________________________________________
Suggest reasonable mechanisms for each of the following reactions. Use curved arrows to show electron fl ow
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (h) Bromine in water 
Using arrows to show the flow of electrons, write a stepwise mechanism for the reaction given below. [If this reaction proceeds via a mechanism for free-radical chain reaction, give three termination steps and be sure to label each elementary step in your mechanism as either “initiation,” “propagation,” or “termination.”] Recall that HCl in H2O exists as H3O+ and Cl −.
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following: (h) Bromine in water 
Complete the following reaction and show the complete arrow-pushing mechanism required to produce the product. Show stereochemistry.  
Determine the mechanism and predict the product of the reaction:  
Write the structure of the major organic product formed in the reaction of 1-methylcyclohexene with each of the following: (h) Bromine in water 
Which is the expected product of the reaction shown?
DRAW THE MOLECULAR STRUCTURE OF THE FOLLOWING REACTION PRODUCT(S). Optically inactive ether from the reaction of (1R,2R)-2-bromocyclopentanol with aqueous NaOH
Give all possible product/products and designate stereoselectivity &/or regioselectivity by using wedges and dashes.   
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.
Which is a bromohydrin? a) 2-bromobutane b) 3-bromobut-1-yne c) 2-bromobut-1-ene d) 4-bromopentan-3-ol e) 2-bromobut-2-ene
The following reactions all involve chemistry of alkenes. Fill in the box with the product(s) that are missing from the chemical reaction equations. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES.
Predict the product:
Predict the product:
Predict the products obtained from the reaction of 1-methylcyclohex-1-ene with diatomic chlorine in water. 
Draw a structural formula for the major product of the reaction shown. 
Draw the organic product of the following reaction. 
Draw the product formed when the structure shown below undergoes a reaction with Br2 in H2O.
Predict the major neutral organic product of the following reaction. Include hydrogen atoms in your structure.
The major product of this reaction exists as two stereoisomers. Draw both isomers. Show all hydrogen atoms in the structures. Use wedge-and-dash bonds to indicate the stereochemistry. 
The reaction of 1-methylcyclopentene with bromine water proceeds via _____ addition and gives the ______ product.a. syn; anti-Markovnikovb. syn; Markovnikovc. anti; Markovnikovd. anti; anti-Markovnikov 
The reaction below produces two major products: draw one. There is one other major organic product. What is its relationship to the compound you drew? structural isomer, enantiomer, confomer, diastereomer
The reaction of 1-methylcyclopentene with bromine water proceeds via _____ addition and gives the _____ product. a. syn: Markovnikov b. anti: Markovnikov c. syn: anti-Markovnikov d. anti: anti-Markovnikov