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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4:21 minutes

Problem 11a,b

Textbook Question

Predict the products of the following reactions.
(a) cyclohexylmethanol + TsCl/pyridine
(b) product of (a) + LiAlH4

Verified step by step guidance

Step 1: Analyze the reaction in part (a). Cyclohexylmethanol reacts with TsCl (tosyl chloride) in the presence of pyridine. Tosyl chloride is commonly used to convert alcohols into tosylates, which are excellent leaving groups. The hydroxyl group (-OH) of cyclohexylmethanol will be replaced by a tosyl group (-OTs). This occurs via nucleophilic substitution, where pyridine acts as a base to neutralize the HCl byproduct.

Step 2: Write the chemical transformation for part (a). Cyclohexylmethanol (C6H11CH2OH) reacts with TsCl to form cyclohexylmethyl tosylate (C6H11CH2OTs). The tosyl group is represented as -SO2C6H4CH3. This step involves the formation of a new bond between the oxygen atom of the alcohol and the sulfur atom of the tosyl group.

Step 3: Analyze the reaction in part (b). The product from part (a), cyclohexylmethyl tosylate, reacts with LiAlH4 (lithium aluminum hydride). LiAlH4 is a strong reducing agent that can reduce alkyl tosylates to alkanes. In this case, the tosyl group (-OTs) will be removed, and the hydrogen atoms from LiAlH4 will replace it, forming cyclohexylmethane.

Step 4: Write the chemical transformation for part (b). Cyclohexylmethyl tosylate (C6H11CH2OTs) reacts with LiAlH4 to form cyclohexylmethane (C6H11CH3). This reduction involves the cleavage of the C-O bond and the addition of hydrogen atoms.

Step 5: Summarize the overall reaction sequence. In part (a), cyclohexylmethanol is converted into cyclohexylmethyl tosylate via reaction with TsCl/pyridine. In part (b), cyclohexylmethyl tosylate is reduced by LiAlH4 to form cyclohexylmethane. These steps demonstrate the use of tosylation to activate an alcohol for subsequent reduction.

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Key Concepts

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

TsCl and Pyridine Reaction

The reaction of alcohols with tosyl chloride (TsCl) in the presence of a base like pyridine converts the alcohol into a tosylate, which is a better leaving group. This transformation facilitates subsequent nucleophilic substitution reactions, allowing for the formation of more reactive intermediates that can undergo further reactions.

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 the reaction products, the tosylate formed from cyclohexylmethanol can undergo substitution with a nucleophile, such as hydride from LiAlH4, leading to the formation of an alcohol or alkane.

LiAlH4 as a Reducing Agent

Lithium aluminum hydride (LiAlH4) is a strong reducing agent commonly used in organic chemistry to reduce carbonyl compounds and other electrophiles. In this case, it can reduce the tosylate product from the first reaction back to an alcohol, effectively restoring the hydroxyl group and completing the transformation of the original alcohol.

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Related Practice

Textbook Question

Show how you would convert propan-1-ol to the following compounds using tosylate intermediates. You may use whatever additional reagents are needed.

c. CH₃CH₂CH₂OCH₂CH₃, ethyl proyl ether

d. CH₃CH₂CH₂CN, butyronitrile

Textbook Question

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

(a) (R)-butan-2-ol + TsCl in pyridine

(b) (S)-2-butyl tosylate + NaBr

Textbook Question

What is the product of each of the following reactions?

Textbook Question

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(b)

Textbook Question

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(a)

Textbook Question

Predict the major product(s) of each of the following reactions.

Textbook Question

Complete the following multistep syntheses using tosylate formation as one of the steps. The optimum number of steps for each synthesis is shown.

(a)

Textbook Question

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(b)

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Predict the products of the following reactions. (a) cyclohexylmethanol + TsCl/pyridine (b) product of (a) + LiAlH4

Key Concepts

TsCl and Pyridine Reaction

Nucleophilic Substitution

LiAlH4 as a Reducing Agent

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Predict the products of the following reactions.
(a) cyclohexylmethanol + TsCl/pyridine
(b) product of (a) + LiAlH4