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

Hydroboration

Organic Chemistry

10. Addition Reactions

Hydroboration

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3:53 minutes

Problem 52d

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
d. trans-2-methylcyclohexanol

Verified step by step guidance

Step 1: Begin by identifying the target compound, trans-2-methylcyclohexanol, and note that it has a hydroxyl group (-OH) and a methyl group (-CH₃) in a trans configuration on a cyclohexane ring. This means the substituents are on opposite sides of the ring plane.

Step 2: Start with methylenecyclohexane, which is a cyclohexane ring with a double bond. Perform hydroboration-oxidation to convert the double bond into an alcohol group. Use BH₃·THF (borane in tetrahydrofuran) followed by H₂O₂/NaOH for oxidation. This reaction will yield cyclohexanol with the hydroxyl group added in an anti-Markovnikov fashion.

Step 3: To introduce the methyl group at the 2-position, perform a regioselective alkylation. First, convert the alcohol group into a leaving group by reacting cyclohexanol with TsCl (tosyl chloride) and pyridine to form a tosylate. Then, use a strong base like NaH to deprotonate the cyclohexane ring, creating a nucleophilic site at the 2-position. React this intermediate with methyl iodide (CH₃I) to add the methyl group.

Step 4: Ensure the trans configuration of the substituents. If the reaction does not yield the desired stereochemistry, use a stereoselective method such as epimerization. This can be achieved by treating the compound with a base like NaOH under controlled conditions to invert the stereochemistry at the 2-position.

Step 5: Purify the product using techniques like recrystallization or chromatography to isolate trans-2-methylcyclohexanol. Confirm the structure and stereochemistry using spectroscopic methods such as NMR and IR.

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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 synthesis pathway is crucial for determining the necessary reagents and conditions to achieve the desired product. This involves knowledge of reaction mechanisms, functional group transformations, and the reactivity of different compounds.

Reagents and Reaction Conditions

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. The choice of reagents and the specific reaction conditions, such as temperature and solvent, can significantly influence the outcome of the synthesis. Familiarity with common reagents and their roles in organic reactions is essential for planning an effective synthesis route.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of synthesizing compounds like trans-2-methylcyclohexanol, understanding stereochemistry is vital to ensure the correct isomer is produced. This includes knowledge of concepts such as chirality, stereoisomers, and the impact of substituent positions on the overall molecular structure.

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Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(m)

Textbook Question

The bulky borane 9-BBN was developed to enhance the selectivity of hydroboration. In this example, 9-BBN adds to the less hindered carbon with 99.3% regioselectivity, compared with only 57% for diborane.

b. 9-BBN is synthesized by adding BH₃ across a symmetric, cyclic diene. What is the structure of the diene?

Textbook Question

Show how you would accomplish the following synthetic conversions.

(b) but-1-ene → butan-2-ol

Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.

(b)

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

a. borane in tetrahydrofuran, followed by basic hydrogen peroxide

Textbook Question

Unlike hydroboration–oxidation, the addition of H₂O catalyzed by H₃O⁺ is not stereospecific. Thinking carefully about the mechanism of the reaction, give two reasons why.

Textbook Question

Draw the products of the following reactions, including their configurations:

Textbook Question

What reagents are needed to carry out the following syntheses?

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