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

22. Carboxylic Acid Derivatives: NAS

Carboxylation

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylation

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2:39 minutes

Problem 39d

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
(d)

Verified step by step guidance

Step 1: Analyze the target molecule and identify the functional groups present. Determine the starting material that can be transformed into the target molecule.

Step 2: Plan the synthesis by identifying key transformations needed to convert the starting material into the target molecule. Consider reactions such as oxidation, reduction, substitution, and addition.

Step 3: Select appropriate reagents and solvents for each transformation. For example, if an oxidation step is required, you might choose reagents like KMnO4 or CrO3.

Step 4: Sequence the reactions logically, ensuring that each step is feasible and that the functional groups are compatible with the chosen reagents. Consider protecting groups if necessary to prevent unwanted reactions.

Step 5: Write out the detailed mechanism for each step, showing how the reagents interact with the starting material to form intermediates and ultimately the target molecule. Use MathML to represent chemical structures and equations where applicable.

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Key Concepts

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

Multistep Synthesis

Multistep synthesis involves a series of chemical reactions that transform starting materials into a desired product through intermediate compounds. Understanding the sequence of reactions, including the reagents and conditions required for each step, is crucial for successfully completing the synthesis. This concept emphasizes the importance of planning and strategy in organic chemistry to achieve complex molecules efficiently.

Reagents and Solvents

Reagents are substances used to bring about a chemical reaction, while solvents are the mediums in which reactions occur. Selecting appropriate reagents is essential for driving the desired transformations, and the choice of solvent can influence reaction rates, yields, and selectivity. Knowledge of common reagents and solvents, along with their properties, is vital for effective synthesis planning.

Reaction Mechanisms

A reaction mechanism describes the step-by-step sequence of elementary reactions that occur during a chemical transformation. Understanding mechanisms helps predict the products of reactions and the conditions needed for them to proceed. Familiarity with common mechanisms, such as nucleophilic substitution or electrophilic addition, is essential for designing multistep syntheses and troubleshooting potential issues.

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Related Practice

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a) trans-1-bromobut-2-ene → trans-pent-3-enoic acid (two ways)

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(b)

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(a) hept-6-en-1-ol → ε-caprolactone

(b) methoxybenzene → p-methoxybenzamide

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(c)

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(a) PhCH₂CH₂OH → PhCH₂CH₂COOH

Textbook Question

When a chemist attempted the following reaction sequence, the desired product was not formed.

(a) Why?

(b) Suggest a solution to the problem. [Think about chemistry from the end of Chapter 13.]

Textbook Question

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

Textbook Question

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(d) butan-2-ol → 2-methylbutanoic acid

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Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.(d)

Key Concepts

Multistep Synthesis

Reagents and Solvents

Reaction Mechanisms

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Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
(d)