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

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - Using HX

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - Using HX

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3:32 minutes

Problem 106a(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.'
(a)

Verified step by step guidance

Identify the functional group in the given molecule. The structure shows a benzyl alcohol, which has a hydroxyl group (-OH) attached to a benzyl group.

Consider the reaction with HCl. The hydroxyl group can be protonated by HCl, forming water, which is a good leaving group.

After the formation of water, a carbocation intermediate is generated. In this case, a benzyl carbocation, which is relatively stable due to resonance with the aromatic ring.

The chloride ion (Cl-) from HCl can then attack the carbocation, leading to the formation of benzyl chloride.

Repeat the same process for HBr. The hydroxyl group is protonated by HBr, forming water as a leaving group, and a benzyl carbocation is formed. The bromide ion (Br-) then attacks the carbocation, resulting in the formation of benzyl bromide.

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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 or react with bases, influencing the reactivity of various functional groups. Understanding how acids interact with different substrates is crucial for predicting reaction outcomes.

Nucleophilicity and Electrophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair, while electrophilicity is the ability to accept an electron pair. In the context of reactions with HCl and HBr, identifying which reactants act as nucleophiles and which as electrophiles helps predict the products formed. This concept is fundamental in determining reaction mechanisms.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants transform into products. They provide insight into the intermediates formed and the energy changes involved. Understanding the mechanism is essential for predicting the products of reactions with acids like HCl and HBr, as it reveals how bonds are broken and formed during the reaction.

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Suggest the appropriate reagents to carry out the following transformations.

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Another method for converting alcohols to chloroalkanes makes use of chlorotrimethylsilane (TMSCl) and DMSO. Suggest a mechanism for this reaction to form (a) a 1° chloroalkane and (b) a 3° chloroalkane. [The reaction begins by the reaction of DMSO and TMSCl and is analogous to the Swern oxidation.]

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Predict the product of the following reactions.

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Predict the product of the following reactions.

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Predict the product of the following reactions.

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(d)

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(a)

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Propose a mechanism for the reaction of

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