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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6:44 minutes

Problem 5

Textbook Question

Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?

Verified step by step guidance

Step 1: Recognize that muscalure is a long-chain alkene with a specific double bond position. Analyze its structure to determine the chain length and the location of the double bond.

Step 2: Plan the synthesis by identifying the need to elongate the carbon chain of 1-bromopentane. Use a coupling reaction, such as the Wurtz reaction, to combine two molecules of 1-bromopentane, forming a 10-carbon alkane (decane).

Step 3: Introduce a double bond into the decane chain. This can be achieved through a dehydrohalogenation reaction. First, convert decane into a halogenated intermediate (e.g., 1-bromodecane) using bromination, and then treat it with a strong base (e.g., KOH or NaOH) to eliminate HBr and form the desired alkene.

Step 4: Ensure the double bond is in the correct position to match the structure of muscalure. If necessary, use a method like isomerization to shift the double bond to the appropriate location.

Step 5: Purify the final product to isolate muscalure. Use techniques such as distillation or chromatography to ensure the product is free of impurities and matches the desired structure.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of synthesizing muscalure from 1-bromopentane, understanding this mechanism is crucial, as it allows for the introduction of functional groups necessary for the final product. The reaction can proceed via either the SN1 or SN2 pathway, depending on the structure of the substrate and the conditions used.

Functional Group Transformation

Functional group transformation involves converting one functional group into another, which is essential in organic synthesis. In the case of muscalure, starting from 1-bromopentane, you may need to transform alkyl halides into alcohols or other functional groups that can be further modified. This concept is vital for understanding how to manipulate the molecular structure to achieve the desired compound.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Muscalure has specific stereochemical requirements for its biological activity as a pheromone. When synthesizing muscalure from 1-bromopentane, it is important to consider the stereochemical outcomes of reactions to ensure that the correct isomer is produced, as different isomers can have vastly different effects.

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