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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5:03 minutes

Problem 37d

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

Verified step by step guidance

Step 1: Begin with bromobenzene as the starting material. Perform a Friedel-Crafts alkylation reaction using propene (CH3-CH=CH2) and a Lewis acid catalyst such as AlCl3. This will introduce a propyl group onto the benzene ring, forming propylbenzene.

Step 2: Oxidize the propyl group on the benzene ring to a propenyl group (CH2=CH-CH2-) using a dehydrohalogenation reaction. This can be achieved by first brominating the benzylic position with NBS (N-Bromosuccinimide) in the presence of light or a radical initiator, followed by elimination using a strong base like KOH or NaOH.

Step 3: Perform a hydroboration-oxidation reaction to convert the terminal alkene group (CH2=CH-) into a primary alcohol (-CH2OH). Use BH3·THF for hydroboration, followed by oxidation with H2O2 and NaOH.

Step 4: Verify the structure of the product, 3-phenylprop-2-en-1-ol, which should now have a benzene ring attached to a three-carbon chain with a double bond between the second and third carbons and a hydroxyl group (-OH) on the first carbon.

Step 5: If needed, purify the product using techniques such as distillation or recrystallization, and confirm its identity using spectroscopic methods like NMR or IR to ensure the correct functional groups are present.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the case of bromobenzene, the bromine atom can be replaced by various electrophiles, allowing for the introduction of different functional groups. Understanding EAS is crucial for manipulating aromatic compounds to synthesize desired products.

Allylic Rearrangement

Allylic rearrangement refers to the migration of a substituent in an allylic position, which can lead to the formation of new double bonds or functional groups. This concept is important when synthesizing compounds like 3-phenylprop-2-en-1-ol, as it allows for the transformation of intermediates into the desired product through the rearrangement of carbon skeletons.

Reagents and Solvents in Organic Synthesis

The choice of reagents and solvents is critical in organic synthesis, as they can influence reaction rates, yields, and selectivity. For synthesizing 3-phenylprop-2-en-1-ol, specific reagents such as bases or catalysts may be required to facilitate reactions like dehydrohalogenation or hydration. Understanding the role of these components is essential for successful synthesis.

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Related Practice

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)

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)

Textbook Question

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

Textbook Question

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

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:

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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

Key Concepts

Electrophilic Aromatic Substitution

Allylic Rearrangement

Reagents and Solvents in Organic Synthesis

Watch next

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