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

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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5:33 minutes

Problem 10a

Textbook Question

How could the following compounds be prepared, using cyclohexene as a starting material?
a.

Verified step by step guidance

Step 1: Begin with cyclohexene as the starting material. Cyclohexene is an alkene, and its double bond can be used as a reactive site for functional group transformations.

Step 2: Perform hydroboration-oxidation to introduce the hydroxyl (-OH) group. Use BH₃ (borane) followed by H₂O₂ (hydrogen peroxide) and NaOH (sodium hydroxide). This reaction adds the hydroxyl group to the less substituted carbon of the double bond, resulting in anti-Markovnikov addition.

Step 3: To introduce the ethyl group (-CH₂CH₃), perform an alkylation reaction. First, convert the hydroxyl group into a good leaving group by treating the alcohol with a reagent like TsCl (tosyl chloride) in the presence of pyridine, forming a tosylate.

Step 4: Carry out a nucleophilic substitution reaction (SN2) using ethyl bromide (CH₃CH₂Br) or ethyl iodide (CH₃CH₂I) as the alkylating agent. The ethyl group will replace the tosylate group, forming the desired product.

Step 5: Ensure stereochemistry is correct. The hydroboration-oxidation step introduces the hydroxyl group in a syn addition, and the SN2 reaction inverts the configuration at the carbon center. Verify that the final product matches the stereochemistry shown in the image.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions are fundamental in organic chemistry, particularly for alkenes like cyclohexene. In these reactions, an electrophile reacts with the double bond of the alkene, leading to the formation of a more stable carbocation intermediate. This process is crucial for synthesizing various compounds from cyclohexene, as it allows for the introduction of different functional groups.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule to form a more stable isomer. In the context of cyclohexene, these reactions can occur after electrophilic addition, where the initial product may undergo shifts in the position of atoms or groups to yield more stable products. Understanding these rearrangements is essential for predicting the final compounds that can be synthesized from cyclohexene.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another. In the preparation of compounds from cyclohexene, various transformations such as oxidation, reduction, or substitution can be employed. Mastery of these transformations is vital for effectively designing synthetic pathways to achieve the desired end products.

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Related Practice

Textbook Question

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(c)

Textbook Question

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

d. 3-phenylprop-2-en-1-ol

Textbook Question

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(e) benzyl alcohol (Ph–CH₂–OH) from bromobenzene (Ph–Br)

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

Textbook Question

Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(c)

Textbook Question

What reagents should be used to carry out the following syntheses?

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