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

10. Addition Reactions

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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3:21 minutes

Problem 52c

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
c. 1-(hydroxymethyl)cyclohexanol

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. Perform a hydroboration-oxidation reaction to convert the double bond into an alcohol group. Use BH₃·THF (borane in tetrahydrofuran) for hydroboration, followed by oxidation with H₂O₂ (hydrogen peroxide) in a basic solution (NaOH). This will yield cyclohexanol.

Step 2: To introduce the hydroxymethyl group, use formaldehyde (HCHO) as the reagent. React cyclohexanol with formaldehyde in the presence of an acid catalyst (e.g., HCl or H₂SO₄) to perform a hydroxymethylation reaction. This will attach a hydroxymethyl group (-CH₂OH) to the cyclohexanol.

Step 3: Ensure the reaction conditions are controlled to avoid overreaction or polymerization of formaldehyde. Monitor the reaction to confirm the formation of 1-(hydroxymethyl)cyclohexanol.

Step 4: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of the compound. This step ensures the removal of any unreacted starting materials or by-products.

Step 5: Confirm the structure of the synthesized compound using spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy). Look for characteristic peaks corresponding to the hydroxyl (-OH) and hydroxymethyl (-CH₂OH) groups.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones through a series of chemical reactions. Understanding the target compound's structure and functional groups is crucial for determining the appropriate reagents and reaction conditions needed to achieve the desired transformation.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of 1-(hydroxymethyl)cyclohexanol, the hydroxymethyl (-CH2OH) group is essential for understanding how to manipulate the starting material, methylenecyclohexane, to introduce this functional group through various reactions.

Reagents and Reaction Mechanisms

Reagents are substances used to bring about a chemical reaction, and understanding their roles is vital for successful synthesis. Different reagents can facilitate various reaction mechanisms, such as nucleophilic substitution or electrophilic addition, which are key to transforming methylenecyclohexane into 1-(hydroxymethyl)cyclohexanol by adding the hydroxymethyl group effectively.

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Related Practice

Textbook Question

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

b. fumaric acid to meso-tartaric acid.

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(e)

Textbook Question

Predict the major products of the following reactions.

f. 1-ethylcycloheptene + cold, dilute KMnO₄

Textbook Question

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

a. fumaric acid to (±)-tartaric acid.

b. fumaric acid to meso-tartaric acid.

Textbook Question

What stereoisomers are obtained from the reaction of each of the following alkenes with OsO₄ followed by aqueous H₂O₂?

a. trans-2-butene

b. cis-2-butene

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)

Textbook Question

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(a)

Textbook Question

Show how you would accomplish the following conversions.

c. trans-hex-3-ene to meso-hexane-3,4-diol

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