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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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3:14 minutes

Problem 31a

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:
a.

Verified step by step guidance

Step 1: Analyze the starting material and target compound. The starting material is bromobenzene, and the target compound is phenylethanol (C6H5CH2CH2OH). This transformation involves replacing the bromine atom with a two-carbon chain containing a hydroxyl group.

Step 2: Perform a nucleophilic substitution reaction. Bromobenzene can undergo a reaction with ethylene oxide (an epoxide containing two carbons) in the presence of a strong base such as NaOH or KOH. This opens the epoxide ring and attaches the two-carbon chain to the benzene ring.

Step 3: Ensure the hydroxyl group is retained. The reaction with ethylene oxide naturally introduces the hydroxyl group at the terminal carbon of the two-carbon chain, forming phenylethanol.

Step 4: Purify the product. After the reaction, the mixture can be purified using techniques such as distillation or recrystallization to isolate phenylethanol.

Step 5: Verify the structure. Use spectroscopic methods such as NMR or IR to confirm the presence of the hydroxyl group and the two-carbon chain attached to the benzene ring.

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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 a series of 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 prepare 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 increase the rate of a reaction without being consumed. In organic synthesis, the choice of reagents and catalysts can significantly influence the efficiency and selectivity of the reaction. Familiarity with common inorganic reagents and catalysts is essential for successfully 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 present in the target compound is vital for determining the appropriate synthetic route. Understanding how different functional groups interact and transform during reactions is key to predicting the outcomes of organic synthesis.

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Related Practice

Textbook Question

Draw perspective structures or Fischer projections for the substitution products of the following reactions.

(b)

Textbook Question

a. Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Give a mechanism for this racemization.

b. In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.

Textbook Question

For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2).

c. 1-iodo-1-methylcyclohexane + ethanol

Textbook Question

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (“Et” is the abbreviation for ethyl.)

Textbook Question

For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (S_N1) or second order (S_N2).

a. 2-chloro-2-methylbutane + CH₃COOH

b. isobutylbromide + sodium methoxide

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

a. butan-1-ol

Textbook Question

Show how you might use S_N2 reactions to convert 1-chlorobutane into the following compounds.

b. 1-fluorobutane

Textbook Question

A solution of pure (S)-2-iodobutane ([α] = +15.90°) in acetone is allowed to react with radioactive iodide, ¹³¹I^–, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°.

b. What does this result suggest about the mechanism of the reaction of 2-iodobutane with iodide ion?

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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:a.

Key Concepts

Organic Synthesis

Reagents and Catalysts

Functional Groups

Watch next

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:
a.