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

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

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2:22 minutes

Problem 62

Textbook Question

Starting with formaldehyde and the alkyl halides shown as the only sources of carbon, provide a synthesis of the following alcohol.

Verified step by step guidance

Step 1: Begin by identifying the target alcohol structure from the image. The alcohol has a hydroxyl group on each end of a carbon chain with a ketone group in the middle. This suggests a synthesis involving multiple carbon-carbon bond formations.

Step 2: Use formaldehyde as the starting material. Formaldehyde can be used to form primary alcohols through reactions such as the Grignard reaction. Consider how formaldehyde can be converted into a longer carbon chain using alkyl halides.

Step 3: Plan the synthesis by considering the formation of the carbon backbone. You can use alkyl halides to extend the carbon chain. For example, a Grignard reagent can be formed from an alkyl halide, which can then react with formaldehyde to form a primary alcohol.

Step 4: Once the carbon chain is extended, introduce the ketone group. This can be done by oxidizing a secondary alcohol to a ketone using an oxidizing agent like PCC (Pyridinium chlorochromate).

Step 5: Finally, ensure the hydroxyl groups are correctly positioned on the carbon chain. This may involve additional reactions such as protection/deprotection strategies or further Grignard reactions to achieve the desired alcohol structure.

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Key Concepts

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

Formaldehyde as a Carbon Source

Formaldehyde (HCHO) is the simplest aldehyde and serves as a versatile carbon source in organic synthesis. It can participate in various reactions, such as nucleophilic additions, where it can react with nucleophiles to form alcohols. Understanding its reactivity is crucial for constructing complex molecules from simpler ones.

Alkyl Halides in Synthesis

Alkyl halides are organic compounds containing a carbon-halogen bond, which can undergo nucleophilic substitution or elimination reactions. They are important intermediates in organic synthesis, allowing for the introduction of functional groups or the formation of new carbon-carbon bonds. Recognizing how to manipulate these compounds is essential for constructing desired alcohols.

Nucleophilic Addition Reactions

Nucleophilic addition reactions involve the attack of a nucleophile on an electrophilic carbon atom, such as that in carbonyl compounds like aldehydes. This reaction is fundamental in organic chemistry for forming alcohols from carbonyl precursors. Understanding the mechanism and conditions for these reactions is vital for successful synthesis.

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