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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2:23 minutes

Problem 39c

Textbook Question

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

Verified step by step guidance

Identify the functional groups present in the starting material and the target molecule. Determine the changes that need to occur, such as the addition or removal of functional groups, or changes in carbon skeleton.

Plan the synthesis by considering possible reactions that can achieve the desired transformations. For example, if you need to add a hydroxyl group, consider reactions like hydroboration-oxidation or epoxidation followed by ring opening.

Determine the order of reactions. Some reactions may need to be performed before others to ensure the correct functional groups are present for subsequent steps. Consider the reactivity and compatibility of functional groups.

Select appropriate reagents and conditions for each step. For example, if you need to perform an oxidation, choose between reagents like PCC, KMnO4, or CrO3 based on the specific transformation and sensitivity of other functional groups.

Draw the reaction mechanism for each step to ensure that the proposed reactions will lead to the desired product. This includes showing the movement of electrons, formation and breaking of bonds, and any intermediates that may form.

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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. Each step typically requires specific reagents and conditions, and understanding the reactivity and compatibility of these reagents is crucial for successful synthesis. This concept is fundamental in organic chemistry for constructing 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. The choice of reagents can influence the reaction pathway and yield, while solvents can affect solubility, reaction rate, and selectivity. Knowledge of common reagents and solvents is essential for planning and executing multistep syntheses.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants are converted into products, detailing the bond-breaking and bond-forming events. Understanding mechanisms helps predict the outcomes of reactions, including the formation of intermediates and the stereochemistry of products. This knowledge is vital for designing effective synthetic routes in organic chemistry.

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Related Practice

Textbook Question

What are the products of the following reactions?

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.

(d)

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?

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

Key Concepts

Multistep Synthesis

Reagents and Solvents

Reaction Mechanisms

Watch next

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