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

8. Elimination Reactions

Cumulative Substitution/Elimination

Organic Chemistry

8. Elimination Reactions

Cumulative Substitution/Elimination

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Problem 106f(v,vi)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'
(f)

Verified step by step guidance

Identify the starting material: The given molecule is a tertiary alcohol, specifically 2-methyl-2-phenylpropan-2-ol.

Step (v) involves two reactions: First, treat the alcohol with TsCl (tosyl chloride) in the presence of Et₃N (triethylamine). This converts the alcohol into a tosylate, a good leaving group.

Next, treat the tosylate with NaOt-Bu (sodium tert-butoxide). This is a strong base, which will likely lead to an elimination reaction, forming an alkene through an E2 mechanism.

Step (vi) involves treating the product with H₂SO₄ (sulfuric acid). In the presence of a strong acid, the alkene may undergo further reactions such as hydration or polymerization, depending on the conditions.

Consider the stability of potential products: The most stable alkene is typically the major product in elimination reactions, following Zaitsev's rule, which favors the formation of the more substituted alkene.

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Key Concepts

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

Reactivity of Alcohols

Alcohols can undergo various reactions depending on their structure and the reagents used. In the presence of TsCl (tosyl chloride) and a base like Et₃N (triethylamine), alcohols can be converted into better leaving groups, facilitating nucleophilic substitution or elimination reactions. Understanding the reactivity of alcohols is crucial for predicting the products of the reactions described.

Nucleophilic Substitution and Elimination Reactions

Nucleophilic substitution (SN1 and SN2) and elimination (E1 and E2) are fundamental reaction mechanisms in organic chemistry. The choice of reagents, such as NaOt-Bu (sodium tert-butoxide), influences whether a substitution or elimination pathway is favored. Recognizing the conditions that favor each mechanism is essential for predicting the outcome of the reactions in the question.

Acid-Catalyzed Reactions

Acid-catalyzed reactions, such as those involving H₂SO₄ (sulfuric acid), often lead to the formation of carbocations, which can rearrange or react with nucleophiles. This concept is vital for understanding how alcohols can be dehydrated to form alkenes or undergo other transformations. Knowing how acids interact with organic molecules helps in predicting the products of the reactions specified.

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Related Practice

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.'

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (iii) SOCl₂, NEt₃. If no reaction occurs, write 'no reaction.'

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ii) PBr₃ If no reaction occurs, write 'no reaction.'

(c)

Textbook Question

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

(c)

Textbook Question

Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(a)

Textbook Question

Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(d)

Textbook Question

Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(e)

Textbook Question

Given the reactants shown, what type of elimination would you expect to occur?

(b)

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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'(f)

Key Concepts

Reactivity of Alcohols

Nucleophilic Substitution and Elimination Reactions

Acid-Catalyzed Reactions

Watch next

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'
(f)