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 - Sulfonyl Chlorides

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions - Sulfonyl Chlorides

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Multiple Choice

Which of the following syntheses would be best to make the given molecule?

The figure illustrates a series of two reactions to obtain a given product. The first reaction contains two reactants. The first reactant has the following structure: A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 4 is dash bonded to O H above. The second reactant is H 2 S O 4 written over the reaction arrow. Delta is written under the reaction arrow.The second reaction contains one reactant. The reactant is N a C N written over the reaction arrow. D M S O is written under the reaction arrow.

The figure illustrates a series of two reactions to obtain a given product. The first reaction contains three reactants. The first reactant has the following structure: A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 4 is dash bonded to O H above. The second reactant is T s C l written over the reaction arrow. The third reactant is N E t 3 written under the reaction arrow.The second reaction contains one reactant. The reactant is N a C N written over the reaction arrow. D M S O is written under the reaction arrow.

The figure illustrates a reaction to obtain a given product. The reaction contains two reactants. The first reactant has the following structure: A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 4 is dash bonded to O H above. The second reactant is N a C N written over the reaction arrow. D M S O is written under the reaction arrow.

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Verified step by step guidance

Identify the target molecule: The target molecule is a nitrile with a cyano group (CN) attached to a chiral center. The stereochemistry is important, as the CN group is on a wedge, indicating a specific configuration.

Consider the starting material: The starting material is an alcohol with the hydroxyl group (OH) on the same chiral center. The goal is to replace the OH group with a CN group while maintaining the stereochemistry.

Evaluate the first synthesis option: The first option involves using H2SO4 and heat, followed by NaCN in DMSO. This method likely involves dehydration to form an alkene, followed by nucleophilic addition of CN. However, this may not retain stereochemistry.

Evaluate the second synthesis option: The second option uses TsCl and NEt3 to convert the alcohol to a tosylate, followed by NaCN in DMSO. This method is likely to proceed via an SN2 mechanism, which inverts stereochemistry.

Evaluate the third synthesis option: The third option uses PBr3 to convert the alcohol to an alkyl bromide, followed by NaCN in DMSO. This method also proceeds via an SN2 mechanism, which inverts stereochemistry. Consider which method best retains or inverts the stereochemistry as needed.