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

9. Alkenes and Alkynes

Dehydration Reaction

Organic Chemistry

9. Alkenes and Alkynes

Dehydration Reaction

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Problem 116

Textbook Question

Suggest a mechanism for the following substitution reaction.

Verified step by step guidance

Analyze the reaction type: Determine whether the substitution reaction proceeds via a radical mechanism, nucleophilic substitution (SN1 or SN2), or another pathway. Based on the problem hint, this reaction likely involves radicals.

Identify the key components: Examine the reactants and products in the reaction image. Look for any halogens, alkyl groups, or other functional groups that may participate in radical formation or propagation.

Initiation step: Propose how radicals are generated in the reaction. This often involves homolytic cleavage of a bond, such as a halogen bond, under the influence of heat or light. Represent this step using MathML, e.g.,

{Cl}_{2} → {Cl}_{•} + {Cl}_{•}

Propagation steps: Suggest how the radicals interact with the substrate to form intermediates and eventually the product. For example, a radical might abstract a hydrogen atom or add to a double bond. Use MathML to represent these steps clearly.

Termination step: Describe how the radicals are quenched to complete the reaction. This could involve two radicals combining to form a stable molecule, e.g.,

{Cl}_{•} + {Cl}_{•} → {Cl}_{2}

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Key Concepts

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

Substitution Reactions

Substitution reactions involve the replacement of one atom or group in a molecule with another atom or group. In organic chemistry, these reactions can be classified into nucleophilic and electrophilic substitutions, depending on the nature of the attacking species. Understanding the mechanism of substitution reactions is crucial for predicting the products and the conditions under which the reaction occurs.

Radical Mechanisms

Radical mechanisms involve species with unpaired electrons, known as radicals, which can initiate reactions by abstracting atoms or groups from other molecules. These mechanisms typically proceed through three main steps: initiation, propagation, and termination. Familiarity with radical mechanisms is essential for analyzing reactions that involve radical intermediates, as they often lead to different products compared to ionic mechanisms.

Reaction Mechanism

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the sequence of bond-breaking and bond-forming events, including the formation of intermediates. Understanding the reaction mechanism is vital for predicting the outcome of a reaction, including the stereochemistry and regioselectivity of the products.

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Related Practice

Textbook Question

Identify the alcohol(s) that would produce the following alkenes under the given conditions.

(c)

Textbook Question

When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]

(a)

Textbook Question

Predict the product of the following pinacol rearrangements.

(c)

Textbook Question

Suggest a mechanism for the following reactions.

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'

(a)

Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

Textbook Question

What product is obtained when the following vicinal diol is heated in an acidic solution?

Textbook Question

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

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