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

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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6:11 minutes

Problem 38d

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.
(d)

Verified step by step guidance

Step 1: Begin with cyclopentanol as the starting material. Convert cyclopentanol into cyclopentyl bromide using phosphorus tribromide (PBr₃) as the reagent. This reaction replaces the hydroxyl group (-OH) with a bromine atom (-Br).

Step 2: Perform a Grignard reaction to introduce the tertiary carbon structure. React cyclopentyl bromide with magnesium in dry ether to form cyclopentyl magnesium bromide, a Grignard reagent.

Step 3: Prepare acetone (CH₃COCH₃) as the electrophile. React the cyclopentyl magnesium bromide with acetone to form a tertiary alcohol intermediate. This step involves nucleophilic attack by the Grignard reagent on the carbonyl group of acetone.

Step 4: Methylate the tertiary alcohol to form the desired ether. Use a methylating agent such as dimethyl sulfate (DMS) or methyl iodide (CH₃I) in the presence of a base like potassium carbonate (K₂CO₃) to replace the hydroxyl group with a methoxy group (-OCH₃).

Step 5: Verify the structure of the final product, ensuring it matches the target compound shown in the image. The final compound should have a cyclopentyl group attached to a tertiary carbon with a methyl group and a methoxy group.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the given compound, the presence of an alkoxy group (–OCH3) indicates that it is an ether, which can influence the reactivity and properties of the compound. Understanding functional groups is essential for predicting how the compound will behave in chemical reactions.

Synthesis Strategies

Synthesis strategies involve the methods and pathways used to construct complex organic molecules from simpler starting materials. In this case, the synthesis of the compound from cyclopentanol and other alcohols requires knowledge of various reactions, such as ether formation or alkylation. Familiarity with these strategies allows chemists to design efficient routes to desired compounds.

Reagents and Solvents

Reagents and solvents play a crucial role in organic synthesis, as they can influence the reaction mechanism and the yield of the desired product. Common reagents may include acids, bases, or catalysts that facilitate the transformation of starting materials. Understanding the properties and roles of these substances is vital for successfully carrying out the synthesis of the target compound.

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Related Practice

Textbook Question

Predict the major products of the following reactions.

(g)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(a)

(b)

Textbook Question

Predict the products of the following reactions.

(d)

(e)

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(d) cyclopentanol → 1-ethylcyclopentanol (two steps)

(e) cyclopentylmethanol → 1-cyclopentylpropan-1-ol (two steps)

Textbook Question

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(e)

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(f)

Textbook Question

What products are obtained from metathesis of each of the following alkenes?

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