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

9. Alkenes and Alkynes

Dehydration Reaction

Organic Chemistry

9. Alkenes and Alkynes

Dehydration Reaction

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4:37 minutes

Problem 37c

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.
c. 1-phenylpropan-2-ol

Verified step by step guidance

Step 1: Begin with bromobenzene as the starting material. Perform a Grignard reaction by reacting bromobenzene with magnesium in anhydrous ether to form phenylmagnesium bromide (a Grignard reagent).

Step 2: React phenylmagnesium bromide with propanal (CH3CH2CHO) to form 1-phenylpropan-2-ol. This reaction involves nucleophilic addition of the Grignard reagent to the carbonyl group of propanal, followed by protonation during workup.

Step 3: To synthesize the target compound (1-phenylpropan-2-ol), ensure the reaction conditions are controlled to avoid side reactions. Use an acidic workup (e.g., HCl or H2O) to protonate the alkoxide intermediate formed during the Grignard reaction.

Step 4: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of 1-phenylpropan-2-ol.

Step 5: Verify the structure of the synthesized compound using spectroscopic methods such as NMR or IR to confirm the presence of the hydroxyl group and the phenyl-propane backbone.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, replacing a leaving group. In the case of bromobenzene, the bromine atom acts as a leaving group, allowing the nucleophile to form a new bond with the carbon. This reaction is crucial for synthesizing alcohols like 1-phenylpropan-2-ol from bromobenzene.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles in organic synthesis. They are formed by reacting alkyl or aryl halides with magnesium in dry ether. In the synthesis of 1-phenylpropan-2-ol, a Grignard reagent can be generated from bromobenzene and then reacted with a suitable carbonyl compound to introduce the propanol group.

Alcohol Synthesis

The synthesis of alcohols is a key transformation in organic chemistry, often involving the reduction of carbonyl compounds or the substitution of halides. In this case, the target compound, 1-phenylpropan-2-ol, can be synthesized by first forming a Grignard reagent and then reacting it with a ketone or aldehyde. Understanding the mechanisms and conditions for these reactions is essential for successful synthesis.

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Related Practice

Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible.

(a) Propose a mechanism for the formation of an alkene from an alcohol.

Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

(d) How might you shift the equilibrium to the right?

Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

(e) How might you shift the equilibrium to the left?

Textbook Question

If the compound shown in the margin is heated in the presence of H₂SO₄,

a. what constitutional isomer would be formed in greatest yield?

b. what stereoisomer would be formed in greater yield?

Textbook Question

Explain why the acid-catalyzed dehydration of an alcohol is a reversible reaction, whereas the base-promoted dehydrohalogenation of an alkyl halide is an irreversible reaction.

Textbook Question

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene

Textbook Question

Explain why the following alcohols, when heated with acid, form the same alkene.

Textbook Question

When the following seven-membered ring alcohol is dehydrated, three alkenes are formed. Propose a mechanism for their formation.

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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. c. 1-phenylpropan-2-ol

Key Concepts

Nucleophilic Substitution

Grignard Reagents

Alcohol 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.
c. 1-phenylpropan-2-ol