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 Multi Step
Addition Retrosynthesis
Addition to Concave vs. Convex Rings

Ozonolysis is a form of oxidative cleavage that breaks through alkenes and replaces them with carbonyls on both ends. Just imagine the ozone functioning like tiny atomic scissors, cutting each alkene right in half!

Concept #1: General properties of ozonolysis.

The products of ozonolysis are a mixture of ketones, aldehydes and formaldehyde. You get these with:

  1. Ends of alkenes with –R groups on both sides = Ketones
  2. Ends of alkenes with 1 –H  = Aldehydes
  3. Ends of alkenes with 2 –Hs (yielding single carbon fragments) = Formaldehyde  

General Reaction:

Practice: Predict the products of the following reaction. 

Additional Problems
Which of the following gives only one organic product on ozonolysis? a) 2-hexyne b) 3-hexyne c) 2-heptyne d) 3-heptyne
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.  O3 / S(CH3)2
All the following reactions have been reported in the chemical literature. Give the structure of the principal organic product in each case.
Circle the only compound that does NOT react with ozone:
Which of these products would result from ozonolysis of (R)-(+)-limonene, followed by reductive workup? The structure of racemic limonene is shown.
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.
Identify the products for the following reaction below.
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 structures below and answer the following questions.  e. Which compounds each form a single product on treatment with O 3 / (CH3)2S?
Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:
What are the major products of the following reaction?
Predict the major product
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.
What are the expected major products from the reaction sequence shown below? a) IV b) V c) I d) II e) III
What will be the major product of the following reactions? Pay careful attention to stereochemistry of the product. 
An unknown alkene gives propanal as the only product upon ozonolysis (reductive workup). When the unknown is treated with bromine in carbon tetrachloride, an optically inactive dibromide is formed, which cannot be resolved into enantiomers. Which of these alkenes is consistent with this data?
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate, if stereoisomers are produced draw one and state the relationship between the other stereoisomer formed. (enantiomers, diastereomers, etc.).
The following molecule undergo ozonolysis with excess ozone to give, after treatment with excess Me2S, more than one product. Show all the possible products.
The following molecule undergo ozonolysis with excess ozone to give, after treatment with excess Me2S, more than one product. Show all the possible products.
The following molecule undergo ozonolysis with excess ozone to give, after treatment with excess Me2S, more than one product. Show all the possible products.
Provide the major product for each of the following alkene reactions. 
What is the expected major product of the following reaction sequence?
Predict the product:
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following:(k) Product of part (j) treated with zinc and water 
Draw the major products for the following reaction.
Supply Reagents:
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following:(k) Product of part (j) treated with zinc and water 
Draw the major products for the following reaction:
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. 
Write the structure of the major organic product formed in the reaction of 1-methylcyclohexene with each of the following:(k) Product of part (j) treated with zinc and water 
Major product of the following reaction is:
Predict the product(s):
What is the expected major product of the reaction sequence shown below?
Draw the products form when the following alkene is treated with O3 followed by Zn, H2O. 
Predict the organic products, in any order, when the following alkene is subjected to ozonolysis with reductive work-up.
What alkyne (or diyne) yields the following oxidative cleavage products? Click the "draw structure" button to launch the drawing utility. 
Give the correct organic products, in any order, for the following ozonolysis reaction: 
Draw the organic product(s) of the following reactions, and include carbon dioxide if it is produced.
The alkene shown below is treated sequentially with ozone (O3) and zinc/acetic acid. Draw structural formula(s) for the organic product(s) formed. 
What is the product of the following reaction? 
Draw the products that are formed when the compound shown below is treated with the following reagents:1. O3, -78°C2. H2O2, H2O
Draw the correct products, in either order, for the following ozonolysis reaction:
Which is product of ozonolysis?  
Draw the major products for the following reaction.
What is the major organic product obtained from the following reaction?
Which of the following conditions and reagents were used to make this compound? Select one: