Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

11. Radical Reactions

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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6:02 minutes

Problem 27

Textbook Question

Write an equation for the reaction of vitamin E with an oxidizing radical (RO•) to give ROH and a less reactive free radical.

Verified step by step guidance

Step 1: Identify the structure of vitamin E from the provided image. Vitamin E is a phenolic compound with a hydroxyl group (-OH) attached to the aromatic ring, which makes it capable of donating a hydrogen atom to neutralize free radicals.

Step 2: Recognize the oxidizing radical (RO·) in the reaction. This radical is highly reactive and can abstract a hydrogen atom from the hydroxyl group of vitamin E.

Step 3: Write the reaction mechanism. The hydroxyl group of vitamin E donates a hydrogen atom to the oxidizing radical (RO·), forming ROH (an alcohol) and leaving behind a less reactive vitamin E radical.

Step 4: Represent the chemical equation using MathML. The reaction can be written as:

Vitamin E + {RO}_{•} \to ROH + {Vitamin E}_{•}

Step 5: Explain the result. The vitamin E radical formed is less reactive and more stable due to resonance stabilization within the aromatic ring. This property allows vitamin E to act as an antioxidant, protecting cells from oxidative damage.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Vitamin E Structure and Function

Vitamin E, primarily composed of tocopherols and tocotrienols, is a fat-soluble antioxidant that protects cell membranes from oxidative damage. Its structure includes a chromanol ring and a long hydrophobic tail, which allows it to integrate into lipid membranes and scavenge free radicals, thus preventing lipid peroxidation.

Radical Reactions

Radical reactions involve species with unpaired electrons, known as radicals, which are highly reactive. In the context of the reaction with vitamin E, the oxidizing radical (RO•) can abstract a hydrogen atom from vitamin E, leading to the formation of a less reactive free radical and an alcohol (ROH). Understanding the mechanism of radical formation and stabilization is crucial for predicting the products of such reactions.

Oxidation-Reduction (Redox) Reactions

Oxidation-reduction reactions involve the transfer of electrons between species, resulting in changes in oxidation states. In this case, vitamin E undergoes oxidation as it donates an electron (or hydrogen atom) to the oxidizing radical, while the radical itself is reduced. Recognizing the roles of oxidizing and reducing agents is essential for balancing redox equations and understanding the overall reaction dynamics.

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Textbook Question

For each reaction, show which stereoisomers are obtained

1. NBS/∆/peroxide

2. Br₂/CH₂Cl₂

Textbook Question

One danger associated with storing ether solvents is their tendency to form explosive peroxides when exposed to oxygen. Suggest a mechanism by which the hydroperoxide might form. You can assume the presence of X• to start the reaction.

Textbook Question

Which ether is most apt to form a peroxide?

Textbook Question

Which ether is least apt to form a peroxide?

Textbook Question

A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C₇H₁₁Br.

a. Draw the resonance forms of the three possible allylic free radical intermediates.

Textbook Question

For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.

(a) cyclohexane

(b) methylcyclopentane

Textbook Question

Using the bond-dissociation energies in Table 5.6,

(a) predict whether or not an iodine radical would be selective for forming a single radical propane.

Textbook Question

What is the major product of the reaction in Problem 7 when the alkane reacts with Cl₂ instead of with Br₂? Disregard stereoisomers.

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