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

Previous problemNext problem

4:45 minutes

Problem 38f

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)

Verified step by step guidance

Step 1: Analyze the target molecule. The compound contains a cyclopentane ring, a methoxy group (-OCH₃) attached to a tertiary carbon, a cyclopropyl group, and a butyl chain. This suggests the need for multiple synthetic steps involving functional group transformations and carbon-carbon bond formation.

Step 2: Start with cyclopentanol as the base structure. Convert cyclopentanol to cyclopentyl bromide using PBr₃ (phosphorus tribromide) to introduce a good leaving group for subsequent reactions.

Step 3: Perform a Grignard reaction to introduce the tertiary carbon center. React cyclopentyl bromide with magnesium in dry ether to form cyclopentyl magnesium bromide. Then, react this Grignard reagent with acetone to form a tertiary alcohol.

Step 4: Convert the tertiary alcohol to the methoxy group (-OCH₃). Use methyl iodide (CH₃I) and a base such as NaH to perform a Williamson ether synthesis, replacing the hydroxyl group with the methoxy group.

Step 5: Introduce the cyclopropyl and butyl groups. Use alkyl halides (e.g., cyclopropyl bromide and butyl bromide) in successive alkylation reactions with the tertiary carbon center, ensuring proper regioselectivity and steric control.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Synthesis of Organic Compounds

Organic synthesis involves the construction of complex organic molecules from simpler ones. This process often requires a series of chemical reactions, including functional group transformations, to achieve the desired structure. Understanding the reactivity of different functional groups and the mechanisms of these reactions is crucial for developing effective synthetic pathways.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the given question, recognizing the functional groups present in the target compound, such as ethers or alcohols, is essential for determining appropriate starting materials and reagents for synthesis.

Reagents and Solvents in Organic Reactions

Reagents are substances used to cause a chemical reaction, while solvents are the mediums in which reactions occur. The choice of reagents and solvents can significantly influence the outcome of a reaction, including yield and selectivity. Familiarity with common reagents and their roles in organic synthesis is vital for successfully developing synthetic routes.

Watch next

Master Intro to Predict the Product with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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

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)

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

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

Textbook Question

What is the product of each of the following reactions?

Textbook Question

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)

Textbook Question

What compound undergoes metathesis to form each of the following compounds?

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

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)

Key Concepts

Synthesis of Organic Compounds

Functional Groups

Reagents and Solvents in Organic Reactions

Watch next

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)