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

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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Problem 10d

Textbook Question

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

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Identify the target compound and analyze its functional groups and structure. Determine the transformations required to convert cyclohexene into the target compound.

Examine the structure of cyclohexene, which is a six-membered ring with one double bond. Consider reactions that can modify the double bond or add functional groups to the ring.

Propose a sequence of reactions based on the functional groups in the target compound. For example, if the target compound contains an alcohol group, consider hydroboration-oxidation or acid-catalyzed hydration of cyclohexene.

If the target compound contains a halogen, consider reactions such as electrophilic addition of halogens (e.g., Br₂ or Cl₂) or hydrohalogenation (e.g., HBr or HCl) to the double bond of cyclohexene.

For more complex functional groups, consider multi-step synthesis. For example, if the target compound contains a ketone, consider oxidizing an alcohol intermediate or performing ozonolysis of cyclohexene to cleave the double bond and form a ketone.

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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 allows for the introduction of various functional groups, which can be crucial for synthesizing different compounds from cyclohexene.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule, often resulting in the formation of more stable isomers. In the context of cyclohexene, these reactions can occur after electrophilic addition, where the initial carbocation may shift to a more stable position. Understanding these rearrangements is essential for predicting the products formed during the synthesis of compounds from cyclohexene.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another, which is vital for organic synthesis. Starting from cyclohexene, various transformations can be employed, such as hydrogenation, halogenation, or oxidation, to create desired products. Mastery of these transformations allows chemists to design synthetic pathways effectively and achieve specific molecular architectures.

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Related Practice

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(a) octane

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(h) cyclooctylmethanol + CH₃CH₂MgBr

(i) potassium tert-butoxide + methyl iodide

(j) sodium methoxide + tert-butyl iodide

Textbook Question

Which of the following alkyl halides could be successfully used to form a Grignard reagent?

Textbook Question

A laboratory student added 1-bromobutane to a flask containing dry ether and magnesium turnings. An exothermic reaction resulted, and the ether boiled vigorously for several minutes. Then she added acetone to the reaction mixture and the ether boiled even more vigorously. She added dilute acid to the mixture and separated the layers. She evaporated the ether layer, and distilled a liquid that boiled at 143 °C. GC–MS analysis of the distillate showed one major product with a few minor impurities. The mass spectrum of the major product is shown here.

(a) Draw out the reactions that took place and show the product that was formed.

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Textbook Question

Starting with cyclohexane, how could the following compounds be prepared?

Textbook Question

A chemist attempted the reaction below, one we introduce in Chapter 17, expecting the reaction between a strong nucleophile and a ketone in water to give an alkoxide product.

(a) Why did the reaction fail?

(b) How could the reaction conditions be changed to give a successful reaction?

Textbook Question

Give the expected products of the following reactions. Include a protonation step where necessary.

(a) 2,2-dimethyloxirane + isopropylmagnesium bromide

(b) propylene oxide + n-butyllithium

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