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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4:54 minutes

Problem 43a

Textbook Question

Give the structures of the intermediates represented by letters J, L, M, and N in this synthesis.

Verified step by step guidance

Step 1: Analyze the starting material and the first reaction. The starting material is an ester (methyl 3-phenylpropanoate). Reaction with LiAlH4 in ether reduces the ester to a primary alcohol. The intermediate J is therefore 3-phenylpropan-1-ol.

Step 2: Intermediate J undergoes a reaction with TsCl (tosyl chloride) in pyridine. This converts the hydroxyl group into a tosylate group, making it a good leaving group. The intermediate L is 3-phenylpropyl tosylate.

Step 3: Intermediate L reacts with KO-tBu (potassium tert-butoxide), which promotes an elimination reaction. This results in the formation of an alkene. The intermediate M is 3-phenylpropene.

Step 4: Intermediate M undergoes bromination with Br2 in water. This results in the anti-addition of bromine and hydroxyl groups across the double bond. The intermediate N is 2-bromo-3-phenylpropan-1-ol.

Step 5: Intermediate N reacts with TIPS-Cl (triisopropylsilyl chloride) in the presence of Et3N (triethylamine). This protects the hydroxyl group by converting it into a silyl ether. The intermediate O is 2-bromo-3-phenylpropan-1-(triisopropylsilyl ether).

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Key Concepts

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

Synthesis Pathways

Synthesis pathways in organic chemistry refer to the series of chemical reactions that transform starting materials into desired products through various intermediates. Understanding these pathways is crucial for predicting the structures of intermediates and the overall reaction mechanism. Each step often involves specific reagents and conditions that facilitate the conversion of one compound to another.

Intermediates

Intermediates are transient species formed during the conversion of reactants to products in a chemical reaction. They are often unstable and can exist for a short time before being transformed into the final product. Identifying intermediates is essential for understanding the reaction mechanism and predicting the outcome of the synthesis, as they can influence the rate and selectivity of the reactions.

Reagents and Conditions

Reagents and conditions are the specific chemicals and environmental factors (like temperature, pressure, and solvent) used in a chemical reaction. Different reagents can lead to different pathways and products, while conditions can affect the reaction rate and equilibrium. Knowledge of common reagents, such as LiAlH4 for reductions or TsCl for activating alcohols, is vital for successfully navigating synthetic routes in organic chemistry.

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Related Practice

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 2:

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(a) trans-cyclopentane-1,2-diol

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(c)

Textbook Question

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

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 1:

Textbook Question

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

(a)

(b)

(c)

Textbook Question

Determine the structures of compounds A through G, including stereochemistry where appropriate.

Textbook Question

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(c)

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