Ch. 11 - Radical 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

The presence of radicals in some familiar looking addition reactions can completely change the product. 

Remember our friendly addition reaction hydrohalogenation? Notice that you achieve Markovnikov alkyl halide in this reaction.  

Concept #1: Overview of Hydrohalogention. 

Now we see this reaction. Note that the only difference is the presence of a radical initiator. 

Concept #2: How Radical Hydrohalogention is different from typical Hydrohalogention.

However, this one added reagent will lead to the formation of an anti-Markovnikov alkyl halide. Here’s the full mechanism:

Provide the complete mechanism for the following radical hydrohalogenation. 

Example #1: Provide the complete mechanism for the following radical hydrohalogenation. 

Additional Problems
What is a key intermediate in the following reaction?
Draw the starting material that, under the given reaction conditions, results in the following products.
Predict the product and show the mechanism for the following synthesis. (You are not required to show any additional resonance structures in the problem)
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.
All the following reactions have been reported in the chemical literature. Give the structure of the principal organic product in each case.
Using curved arrows, draw the mechanism for radical addition of HBr to 1-butene demonstrating initiation, propagation and termination steps. 
Suggest reasonable mechanisms for each of the following reactions. Use curved arrows to show electron flow.
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (c) Hydrogen bromide in the presence of peroxides 
Fill in the box with the product(s) that are missing from the chemical reaction equation. 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.
Write the structure of the major organic product formed in the reaction of 2-methyl-2-butene with each of the following: (c) Hydrogen bromide in the presence of peroxides
Complete the following reaction and show the complete arrow-pushing mechanism required to produce the product. (7 steps: 1 Initiation, 3 Propagation, 3 Termination steps)
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: (c) Hydrogen bromide in the presence of peroxides 
Predict the reagents required to complete the following transformation. 
Predict the major product
Propose a mechanism for the following reaction.
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.
Show the appropriate arrow pushing on the left side of the equation and write the structure after the first immediate step on the right side. (please re-write the reagent where necessary)
A bromine radical can add to the π bond of 2-methylpropene. Use correct arrow formalism to show this process and the expected result. 
Predict the product:
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. 
Major product of the following reaction is: 
Draw the structure of the product(s) of the following reaction. If a mixture of stereoisomers or regioisomers is expected, draw the structures of all expected products.
What is the reagent for the following reaction?
What is the major product of the following reaction?
Provide missing curved arrows and draw the product of the radical addition mechanistic step. Remember to draw any unpaired electrons and lone pairs in the product.