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

Halogenation is one of the most popular addition reactions and is the primary method for making vicinal dihalides

Concept #1: General properties of halogenation. 

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

General Reaction:

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

1. Electrophilic Addition

2. Nucleophilic Substitution (SN2)

Additional Problems
Specify reagents suitable for converting 3-ethyl-2-pentene to each of the following: (a) 2,3-Dibromo-3-ethylpentane 
Predict the product(s) or reagents of the following reactions.
The electrophilic addition of Cl 2 to (E)-2-butene gives a product that is different from the electrophilic addition of Cl2 to (Z)-2-butene. (a) Using arrows to show the flow of electrons, write a stepwise mechanism for each of these two reactions. Be sure to show clearly the stereochemistry associated with each step in each of your two mechanisms and how it connects the stereochemistry of the starting alkene with the stereochemistry of the product. Be sure to label as R or S each chirality center in each of your products.    (b) Is the product of either of these two reactions optically active? ( yes or no; choose one) Provide a detailed, but concise, explanation for your choice. 
Provide the structural formula for the reactant in the following reaction.     
Draw the product(s) from the following reaction. a) clearly label each drawing with the correct stereochemistry-(use R & S for chiral centers, if any). b) clearly label pairs of enantiomers & diastereomers, if any.
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.
The reaction of Br2 to cyclohexene would produce the compound(s) represented by structure(s): Circle all that apply  
Predict the following products of the following reaction:  
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following:  (g) Bromine in carbon tetrachloride
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following: (g) Bromine in carbon tetrachloride 
Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would be a) a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial.  b) a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial.  c) a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial.  d) a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. 
Br2 will also react with alkenes to do electrophilic addition reactions. This is a non-radical reaction that has an interesting stereochemical outcome. Treatment of the optically-active methylcyclohexane shown below with bromine gives the product where Br2 has been added across the double bond. a. Draw all possible stereoisomers that might be obtained. Use the “flat-ring” wedge/dash convention. Be sure that the methyl group is on the topmost carbon in all your structures. Each structure will be in a separate box with a roman numeral designator. b. For EACH chiral carbon, label its stereochemistry as R or S. c. Which structures are diasteromers? Use the roman numeral designators for this answer. If there are no diastereomers, write NONE. d. Which structures are meso? Use the roman numeral designators for this answer. If there are no meso structures, write NONE.
Consider the strucutres below and answer the following questions.  c. Which compounds each form an achiral product by reaction with chlorine? 
Predict the following products of the following reaction (there may be more than one correct answer): 
Consider the reaction given below. (a and b) Give the absolute configuration (R or S) for each of the indicated chiral centers. (c) Using arrows to show the flow of electrons, write a stepwise mechanism for this reaction. Be sure to show the stereochemistry that exists in each elementary step. Also be sure to show clearly how the chiral centers in the final product are formed.
Write the structure of the major organic product formed in the reaction of 1-methylcyclohexene with each of the following: (g) Bromine in carbon tetrachloride 
Propose a mechanism for the following reaction
How many atoms and electrons are directly involved in the bond-making and bond-breaking in the first step of the reaction of bromine with an alkene?   (A) three atoms, four electrons (B) three atoms, six electrons (C) four atoms, four electrons (D) four atoms, six electrons (E) five atoms, four electrons  (F) five atoms, six electrons
Which Newman projection represents the product of the reaction shown?  
Draw the product(s) from the following reaction. a) Clearly label each drawing with the correct stereochemistry-(use R & S for chiral centers, if any). b) Clearly label pairs of enantiomers & diastereomers, if any.
Complete the following reaction by drawing the structure of the principal major product. Indicate relative stereochemistry where necessary. If there is no reaction, write NR.
Which of the statements is most correct regarding the products expected from the halogenation reaction shown below? a) Equal amounts of I and IV are produced. b) Equal amounts of I and III are produced. c) Equal amounts of III and IV are produced. d) Equal amounts of I and II are produced. e) Equal amounts of II and III are produced.
One of the two 2-butene stereoisomers reacts with Cl 2 to give a pair of 2,3-dichlorobutane meso compounds. Is it cis or trans?
For the reaction sequence below, select the expected major product. 
Provide the  products for the following reaction. a) clearly label each drawing with the correct  regio- and stereochemistry. b) clearly label pairs of enantiomers & diastereomers, if any.
Predict the product WITH Stereochemistry:
Predict the major product for the following one-step reaction: 
Draw the organic product(s) formed in the following reaction.One organic product(s) will form.Draw the organic product:
Draw a structural formula for the major organic product of the following reaction.
Draw the product(s) that you would expect for the following reaction. Show stereochemistry, if applicable, by clearly drawing one wedged, one hashed, and two in-plane bonds per stereocenter.
Predict the major organic product of the following reaction. Include hydrogen atoms in your structure. 
Predict the product of the following reaction. Draw all hydrogen atoms.
Draw a structural formula for the major organic product of the following reaction:  
Which of the following is the product formed by the chlorination of 1-butene?a. 1-chlorobutaneb. 2-chlorobutanec. 1,1-dichlorobutaned. 1,2-dichlorobutane 
For the reaction in the image below, if X2 represents Cl2, what is the systematic IUPAC name of the product in the reaction? 
Draw a structural formula for the intermediate m the following reaction: 
Characterize the following alkene as having the E or Z configuration. Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge-and-dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. 
Draw the bridged bromonium ion that is formed as an intermediate during the bromination of this alkene. Include hydrogen atoms, nonbonding electrons, and formal charge(s) in your structure. 
Predict the major product for the following reaction.  
What product is expected from bromination of the following molecule? Remember to show relative stereochemistry. 
Draw a structural formula for the intermediate m the following reaction: