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 106c(vi)

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)

Verified step by step guidance

Step 1: Identify the functional groups present in the molecule. Look at the structure provided in the image and determine if there are any functional groups that are reactive under acidic conditions, such as alcohols, alkenes, or ethers.

Step 2: Consider the role of H₂SO₄ in organic reactions. Sulfuric acid is a strong acid and can act as a catalyst in dehydration reactions, especially with alcohols, leading to the formation of alkenes.

Step 3: Analyze the molecule for any alcohol groups. If an alcohol group is present, H₂SO₄ can protonate the hydroxyl group, making it a better leaving group and facilitating the formation of a carbocation.

Step 4: Determine if a carbocation rearrangement is possible. Once a carbocation is formed, check if it can rearrange to a more stable carbocation, which is common in reactions involving H₂SO₄.

Step 5: Predict the final product. If the molecule contains an alcohol, the reaction may lead to the formation of an alkene through dehydration. If no reactive functional groups are present, conclude 'no reaction.'

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Key Concepts

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

Acid-Base Reactions

In organic chemistry, acid-base reactions involve the transfer of protons (H⁺) between molecules. Strong acids, like sulfuric acid (H₂SO₄), can donate protons to bases, facilitating various reactions such as dehydration or protonation. Understanding the role of acids and bases is crucial for predicting the products of reactions involving H₂SO₄.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, leading to the formation of a more saturated product. In the presence of H₂SO₄, alkenes can undergo electrophilic addition, where the double bond acts as a nucleophile, reacting with the electrophilic sulfuric acid to form alkyl hydrogen sulfate intermediates.

Reaction Conditions and Mechanisms

The conditions under which a reaction occurs significantly influence the mechanism and products formed. In the case of H₂SO₄, the reaction conditions can lead to dehydration, rearrangements, or even no reaction, depending on the structure of the reactants. Analyzing the molecular structure and the reaction environment is essential for accurately predicting the outcome.

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Related Practice

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

(k)

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

(f)

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