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(vii,viii)

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)

Verified step by step guidance

Identify the functional groups present in the molecule. The given molecule is a diol, specifically a 1,2-diol, with hydroxyl groups on adjacent carbon atoms.

Consider the reaction conditions: (vii) HCl and (viii) HBr. Both are strong acids and can protonate the hydroxyl groups, making them better leaving groups.

For reaction with HCl: Protonation of one of the hydroxyl groups will occur, forming a good leaving group (water). This can lead to the formation of a carbocation intermediate.

Assess the stability of the carbocation. In this case, the carbocation formed after the departure of water is a secondary carbocation, which can undergo rearrangement if a more stable carbocation is possible.

For reaction with HBr: Similar to HCl, protonation of the hydroxyl group will occur, leading to the formation of a carbocation. The bromide ion can then attack the carbocation, resulting in the substitution of the hydroxyl group with a bromine atom.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, strong acids like HCl and HBr can protonate nucleophiles, making them more reactive. Understanding how these acids interact with different functional groups is crucial for predicting the products of reactions.

Nucleophilicity and Electrophilicity

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles accept an electron pair. The strength of nucleophiles and electrophiles determines the outcome of reactions. Recognizing which molecules act as nucleophiles or electrophiles in the presence of HCl or HBr is essential for predicting reaction products.

Reaction Mechanisms

Understanding reaction mechanisms is vital for predicting the products of chemical reactions. Mechanisms describe the step-by-step process of how reactants transform into products, including the formation and breaking of bonds. Familiarity with common mechanisms, such as nucleophilic substitution or electrophilic addition, helps in anticipating the outcomes of reactions with acids like HCl and HBr.

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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: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(k)

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

(f)

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)

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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)

Key Concepts

Acid-Base Reactions

Nucleophilicity and Electrophilicity

Reaction Mechanisms

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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)