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 problem

5:14 minutes

Problem 41f

Textbook Question

Design a synthesis for each of the following, using an intramolecular reaction:
f.

Verified step by step guidance

Step 1: Analyze the target molecule. The structure contains a tetrahydrofuran ring (a five-membered cyclic ether) with a hydroxyl group attached to a propyl chain. This suggests the use of an intramolecular reaction to form the cyclic ether.

Step 2: Identify the precursor molecule. To form the tetrahydrofuran ring via an intramolecular reaction, the precursor should contain both a hydroxyl group and a leaving group (such as a halide or tosylate) on the same molecule, separated by a suitable chain length.

Step 3: Propose the starting material. A suitable starting material could be 4-hydroxybutyl bromide or 4-hydroxybutyl tosylate. This molecule contains both the hydroxyl group and the leaving group required for the intramolecular reaction.

Step 4: Describe the reaction mechanism. The intramolecular reaction proceeds via an SN2 mechanism, where the hydroxyl group is deprotonated to form an alkoxide ion (a strong nucleophile). The alkoxide then attacks the carbon attached to the leaving group, forming the cyclic ether (tetrahydrofuran).

Step 5: Outline the synthesis steps. First, prepare the precursor by functionalizing 1,4-butanediol to introduce a leaving group (e.g., bromide or tosylate) on one end. Then, treat the precursor with a strong base (e.g., NaH or KOH) to deprotonate the hydroxyl group and initiate the intramolecular SN2 reaction, yielding the target molecule.

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Key Concepts

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

Intramolecular Reactions

Intramolecular reactions occur when a reaction takes place within a single molecule, leading to the formation of a cyclic structure or a new functional group. These reactions often involve the formation of a bond between two reactive sites within the same molecule, which can significantly enhance the efficiency of the synthesis process. Understanding the mechanisms and conditions that favor intramolecular reactions is crucial for designing effective synthetic pathways.

Synthesis Design

Synthesis design in organic chemistry involves planning a series of chemical reactions to construct a specific target molecule from simpler starting materials. This process requires knowledge of reaction mechanisms, functional group transformations, and the ability to predict the outcomes of reactions. A well-designed synthesis not only considers the efficiency and yield but also the selectivity and safety of the reactions involved.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They dictate the reactivity and properties of organic compounds, making it essential to identify and manipulate them during synthesis. Understanding how different functional groups interact and transform during intramolecular reactions is key to successfully designing a synthesis.

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