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

Solution: A graduate student was attempting to functionalize an alkane for a research project to make her advisor happy. While characterizing the products of her radical bromination reaction, she isolated the byproduct 2,3,3,4,4,5-hexamethylhexane (below). Please answer the following questions concerning the radical reaction. a. Provide the overall reaction scheme for the desired radical bromination. You will need to determine what the starting materials were, reaction conditions, as well as the major products. b. Provide a detailed mechanism including all three parts of radical bromination to show how the isolated side product 2,3,3,4,4,5-hexamethylhexane was formed. c. Other than resonance, what explains the stabilization of alkyl radicals? Provide the name of this stabilization and using both pictures and words, explain this term.

Solution: A graduate student was attempting to functionalize an alkane for a research project to make her advisor happy. While characterizing the products of her radical bromination reaction, she isolated the b

Problem

A graduate student was attempting to functionalize an alkane for a research project to make her advisor happy. While characterizing the products of her radical bromination reaction, she isolated the byproduct 2,3,3,4,4,5-hexamethylhexane (below). Please answer the following questions concerning the radical reaction.

a. Provide the overall reaction scheme for the desired radical bromination. You will need to determine what the starting materials were, reaction conditions, as well as the major products.

b. Provide a detailed mechanism including all three parts of radical bromination to show how the isolated side product 2,3,3,4,4,5-hexamethylhexane was formed.

c. Other than resonance, what explains the stabilization of alkyl radicals? Provide the name of this stabilization and using both pictures and words, explain this term.