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

Leaving Group Conversions Summary

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

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2:47 minutes

Problem 56g

Textbook Question

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.
(g)

Verified step by step guidance

Step 1: Analyze the target molecule. The compound contains a nitrile group (-C≡N) attached to a carbon atom that is also bonded to a hydrogen atom, a methyl group (-CH3), and an ethyl group (-CH2CH3). This suggests that the synthesis involves forming a nitrile group and constructing the correct carbon framework.

Step 2: Start with a suitable alcohol as the starting material. Since alcohols with four or fewer carbon atoms are allowed, choose 2-butanol (CH3CH(OH)CH2CH3) as the starting material. This alcohol has the correct carbon framework to form the desired product.

Step 3: Convert the alcohol to a halide. Use a reagent like thionyl chloride (SOCl2) or phosphorus tribromide (PBr3) to convert 2-butanol into 2-bromobutane (CH3CH(Br)CH2CH3). This step introduces a good leaving group for subsequent reactions.

Step 4: Perform a nucleophilic substitution reaction to introduce the nitrile group. React 2-bromobutane with sodium cyanide (NaCN) in an appropriate solvent like dimethyl sulfoxide (DMSO). This reaction replaces the bromine atom with a nitrile group, forming 2-butanenitrile (CH3CH(C≡N)CH2CH3).

Step 5: Ensure stereochemistry. If the target molecule requires a specific stereochemistry (e.g., the hydrogen and nitrile group are on opposite sides of the carbon atom), use appropriate conditions or reagents to control the stereochemistry during the substitution step. Verify the stereochemistry of the product using spectroscopic methods like NMR.

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Key Concepts

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

Alcohols as Reactants

Alcohols are organic compounds containing one or more hydroxyl (-OH) groups. In synthesis, they can act as nucleophiles or electrophiles depending on the reaction conditions. Understanding the reactivity of different alcohols, especially those with four or fewer carbon atoms, is crucial for designing synthetic pathways to target compounds.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through various chemical reactions. This concept is essential in organic synthesis, as it allows chemists to modify the structure of starting materials to create desired products. Familiarity with common transformations, such as oxidation, reduction, and substitution, is vital for effective synthesis.

Reagents and Solvents in Organic Synthesis

Reagents and solvents play a critical role in organic synthesis by influencing reaction mechanisms and outcomes. In this context, inorganic reagents may be used to facilitate transformations, while solvents can affect solubility and reaction rates. Understanding the properties and roles of different reagents and solvents is essential for optimizing synthetic routes.

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Related Practice

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(e)

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH₃)₃ as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Textbook Question

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(d) concentrated HBr

(e) TsCl/pyridine, then NaBr

Textbook Question

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(a) PBr₃

(b) SOCl₂

Textbook Question

Suggest how you would convert trans-4-methylcyclohexanol to

a. trans-1-chloro-4-methylcyclohexane.

b. cis-1-chloro-4-methylcyclohexane.