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

16. Conjugated Systems

Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Organic Chemistry

16. Conjugated Systems

Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

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6:59 minutes

Problem 90(1)

Textbook Question

a. How could each of the following compounds be prepared from a hydrocarbon in a single step?
b. What other organic compound would be obtained from each synthesis?
1.

Verified step by step guidance

Step 1: Analyze the target compound. The structure contains a bromine atom and a hydroxyl group attached to a cyclohexene ring. This suggests that the reaction involves an electrophilic addition to an alkene.

Step 2: Identify the starting hydrocarbon. The simplest hydrocarbon precursor would be cyclohexene, which contains the double bond necessary for the addition reaction.

Step 3: Determine the reagents required for the transformation. To add both a bromine atom and a hydroxyl group in a single step, use bromine (Br₂) in the presence of water (H₂O). This reaction is known as halohydrin formation.

Step 4: Describe the reaction mechanism. The double bond in cyclohexene reacts with bromine to form a bromonium ion intermediate. Water then attacks the more substituted carbon of the bromonium ion, leading to the formation of the halohydrin.

Step 5: Identify the byproduct. The reaction produces hydrobromic acid (HBr) as a byproduct due to the proton transfer during the halohydrin formation process.

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Key Concepts

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

Hydrohalogenation

Hydrohalogenation is a chemical reaction where a hydrocarbon reacts with a hydrogen halide (HX) to form an alkyl halide. In the context of aromatic compounds, this reaction can lead to the substitution of hydrogen atoms with halogen atoms, such as bromine. This process is crucial for synthesizing compounds like brominated phenols from hydrocarbons in a single step.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This mechanism is essential for understanding how bromine can be introduced to a phenolic compound, resulting in the formation of brominated phenols. The presence of the hydroxyl group enhances the reactivity of the aromatic ring towards electrophiles.

Byproducts in Organic Reactions

In organic synthesis, reactions often yield byproducts alongside the desired product. Understanding the potential byproducts is important for predicting reaction outcomes and optimizing conditions. For example, when synthesizing brominated phenols, other organic compounds, such as hydrogen bromide (HBr), may be produced, which can influence the reaction environment and subsequent steps in the synthesis.

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Related Practice

Textbook Question

When Br₂ is added to buta-1,3-diene at –15 °C, the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 60 °C, the product ratio is 10% A and 90% B.

d. If you had a solution of pure A, and its temperature were raised to 60 °C, what would you expect to happen? Propose a mechanism to support your prediction.

Textbook Question

What are the products of the following reactions, assuming that one equivalent of each reagent is used in each reaction? Disregard stereoisomers.

Textbook Question

How many stereoisomers of each product could be obtained?

Textbook Question

What are the products of the following reactions, assuming that one equivalent of each reagent is used in each reaction?

Textbook Question

a. When HBr adds to a conjugated diene, what is the rate-determining step?

b. When HBr adds to a conjugated diene, what is the product-determining step?

Textbook Question

Draw the major products obtained from the reaction of one equivalent of HCl with the following compounds. For each reaction, indicate the kinetic and thermodynamic products.

a. 2,3-dimethyl-1,3-pentadiene

Textbook Question

What are the products of the following reaction?

Multiple Choice

Predict the major, organic product for the following reaction.

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