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 106k(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.'
(k)

Verified step by step guidance

Step 1: Analyze the structure of the given molecule. The molecule is a cyclohexane ring with a hydroxyl group (OH) attached to it. Additionally, there is a tert-butyl group attached to the ring.

Step 2: Consider the reaction conditions (v) 1. TsCl, Et₃N 2. NaOt-Bu. The first step involves the conversion of the alcohol group to a tosylate using TsCl and Et₃N. This makes the hydroxyl group a better leaving group.

Step 3: In the second step of condition (v), NaOt-Bu is a strong base that can facilitate an elimination reaction, likely leading to the formation of an alkene by removing a proton adjacent to the tosylate group.

Step 4: Consider the reaction conditions (vi) H₂SO₄. Sulfuric acid is a strong acid that can protonate the alcohol group, potentially leading to dehydration and formation of an alkene through an E1 mechanism.

Step 5: Evaluate the possibility of no reaction. Given the strong acidic conditions and the presence of a good leaving group, it is likely that a reaction will occur, leading to the formation of an alkene.

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Key Concepts

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

Reagents and Their Functions

Understanding the role of reagents like TsCl (tosyl chloride) and Et₃N (triethylamine) is crucial. TsCl is used to convert alcohols into better leaving groups, while Et₃N acts as a base to deprotonate the resulting intermediate. This transformation is essential for facilitating nucleophilic substitution reactions.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution reactions can occur via two main mechanisms: SN1 and SN2. SN1 involves a two-step process where the leaving group departs first, forming a carbocation, while SN2 is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs. The choice of mechanism depends on the substrate structure and reaction conditions.

Acid-Base Reactions and Conditions

The presence of H₂SO₄ indicates an acidic environment that can promote dehydration reactions or protonation of nucleophiles. Understanding how acids can influence the reactivity of substrates and the stability of intermediates is vital for predicting the outcome of reactions, including whether a reaction will occur or result in 'no reaction.'

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Related Practice

Textbook Question

Show a mechanism for the following elimination reactions. Label the mechanism as E1 or E2.

(d)

Textbook Question

Paying close attention to the stereochemical outcome, predict the product of these elimination reactions.

(d)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃ ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ 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: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(o)

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)

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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.'(k)

Key Concepts

Reagents and Their Functions

Nucleophilic Substitution Mechanisms

Acid-Base Reactions and Conditions

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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.'
(k)