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

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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4:05 minutes

Problem 31b

Textbook Question

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:
b.

Verified step by step guidance

Step 1: Analyze the transformation. The starting material is 2-methylpropan-1-ol (CH₃CH(CH₃)CH₂OH), and the target compound is 2-methylpentan-1-ol (CH₃CH(CH₃)CH₂CH₂CH₂OH). This involves the addition of a two-carbon chain to the starting material.

Step 2: Identify the reagents needed for chain extension. To add a two-carbon chain, you can use an alkyl halide such as ethyl bromide (CH₃CH₂Br) and a strong base like sodium hydride (NaH) to generate a nucleophile from the alcohol group.

Step 3: Convert the alcohol group into a nucleophile. Treat the starting alcohol with NaH to deprotonate the hydroxyl group, forming the alkoxide ion (CH₃CH(CH₃)CH₂O⁻). This alkoxide ion is a strong nucleophile.

Step 4: Perform the nucleophilic substitution reaction. React the alkoxide ion with ethyl bromide (CH₃CH₂Br) in an SN2 reaction. The alkoxide ion attacks the carbon bonded to the bromine, displacing the bromine and forming the extended chain.

Step 5: Verify the product structure. The reaction yields 2-methylpentan-1-ol (CH₃CH(CH₃)CH₂CH₂CH₂OH), which matches the target compound. Ensure the reaction conditions are controlled to avoid side reactions.

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Key Concepts

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

Organic Synthesis

Organic synthesis is the process of constructing organic compounds through chemical reactions. It involves the strategic selection of starting materials, reagents, and conditions to achieve the desired product. Understanding the principles of organic synthesis is crucial for designing pathways to synthesize specific compounds, especially when limited to certain reagents and carbon chain lengths.

Reagents and Catalysts

Reagents are substances that are added to a reaction to cause a chemical change, while catalysts are substances that speed up a reaction without being consumed. In organic synthesis, the choice of reagents and catalysts can significantly influence the reaction pathway and yield. Familiarity with common inorganic reagents and catalysts is essential for effectively preparing organic compounds.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups in both the starting materials and the target compounds is vital for predicting reactivity and determining the necessary synthetic steps. Understanding how different functional groups interact can guide the selection of appropriate reagents and conditions for synthesis.

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Textbook Question

Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the following compounds. Any of these products may be used as starting materials in subsequent parts of this problem.

d. 3-phenylprop-2-en-1-ol

Textbook Question

Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting material and any other necessary reagents.

(e) benzyl alcohol (Ph–CH₂–OH) from bromobenzene (Ph–Br)

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

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How could the following compounds be prepared, using cyclohexene as a starting material?

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Which of the reactions cannot be used for the synthesis of isobutyl alcohol?

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For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(c)

Textbook Question

What reagents should be used to carry out the following syntheses?

Textbook Question

What reagents should be used to carry out the following syntheses?

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