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

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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5:25 minutes

Problem 21a

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(a) octane

Verified step by step guidance

Identify the target molecule, octane, which is a straight-chain alkane with eight carbon atoms (C₈H₁₈). The goal is to construct this molecule using smaller alkyl halides, vinyl halides, or aryl halides containing no more than six carbon atoms.

Choose a synthetic strategy. Since octane is a simple alkane, a logical approach is to use a coupling reaction, such as the Wurtz reaction, which involves the coupling of two alkyl halides in the presence of sodium metal to form a longer alkane.

Select appropriate starting materials. To synthesize octane, you can use two alkyl halides with four carbon atoms each, such as 1-bromobutane (C₄H₉Br). This ensures that the total number of carbons in the product will be eight.

Write the reaction mechanism. In the Wurtz reaction, two molecules of 1-bromobutane react with sodium metal in a dry ether solvent. The sodium metal donates electrons to the alkyl halides, forming alkyl radicals, which then couple to form octane. The reaction can be represented as:

{C 4}_{(H 9)} Br + {C 4}_{(H 9)} Br + 2 Na \to {C 8}_{(H 18)} + 2 NaBr

Verify the product. After the reaction, confirm that the product is octane by analyzing its structure and ensuring it matches the target molecule. Additionally, ensure that no side reactions or byproducts interfere with the synthesis.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds derived from alkanes by replacing one or more hydrogen atoms with halogen atoms (e.g., Cl, Br, I). They serve as important intermediates in organic synthesis, allowing for the formation of various functional groups through nucleophilic substitution or elimination reactions. Understanding their reactivity is crucial for designing synthetic pathways.

Vinyl and Aryl Halides

Vinyl halides contain a halogen atom bonded to a carbon-carbon double bond, while aryl halides have a halogen atom attached to an aromatic ring. These compounds exhibit unique reactivity patterns due to the presence of π bonds or resonance stabilization, which can influence the types of reactions they undergo. Their roles in synthesis often involve coupling reactions or nucleophilic substitutions.

Synthesis Strategies

Synthesis strategies in organic chemistry involve planning a series of chemical reactions to construct a target molecule from simpler precursors. Techniques such as chain elongation, functional group transformations, and coupling reactions are commonly employed. For synthesizing octane, one might consider using alkyl halides in nucleophilic substitution reactions or coupling reactions to build the carbon chain effectively.

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Related Practice

Textbook Question

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

b. Ph₃COH

Textbook Question

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(a)

Textbook Question

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(a)

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(h) cyclooctylmethanol + CH₃CH₂MgBr

(i) potassium tert-butoxide + methyl iodide

(j) sodium methoxide + tert-butyl iodide

Textbook Question

Which of the following alkyl halides could be successfully used to form a Grignard reagent?

Textbook Question

How could the following compounds be prepared, using cyclohexene as a starting material?

Textbook Question

A laboratory student added 1-bromobutane to a flask containing dry ether and magnesium turnings. An exothermic reaction resulted, and the ether boiled vigorously for several minutes. Then she added acetone to the reaction mixture and the ether boiled even more vigorously. She added dilute acid to the mixture and separated the layers. She evaporated the ether layer, and distilled a liquid that boiled at 143 °C. GC–MS analysis of the distillate showed one major product with a few minor impurities. The mass spectrum of the major product is shown here.

(a) Draw out the reactions that took place and show the product that was formed.

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Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms. (a) octane

Key Concepts

Alkyl Halides

Vinyl and Aryl Halides

Synthesis Strategies

Watch next

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(a) octane