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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1:02 minutes

Problem 11f

Textbook Question

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(f) allyl iodide → but-3-enoic acid

Verified step by step guidance

Step 1: Begin by identifying the functional groups in the starting material (allyl iodide) and the target molecule (but-3-enoic acid). Allyl iodide contains an alkyl halide group, while but-3-enoic acid contains a carboxylic acid group and a double bond.

Step 2: Plan the synthesis by considering the transformation of the alkyl halide into a carboxylic acid. A common method involves converting the alkyl halide into a Grignard reagent, which can then react with carbon dioxide to form a carboxylic acid.

Step 3: React allyl iodide with magnesium in dry ether to form allyl magnesium iodide, a Grignard reagent. The reaction can be represented as:

{CH (2) CH (2) I}_{+ Mg} \to CH (2) CH (2) MgI

Step 4: Bubble carbon dioxide gas through the Grignard reagent solution to form the carboxylic acid intermediate. The reaction can be represented as:

{CH (2) CH (2) MgI}_{+ CO 2} \to CH (2) CH (2) COOH

Step 5: Perform an acidic workup (e.g., using dilute HCl) to protonate the carboxylate ion and isolate the final product, but-3-enoic acid. This step ensures the carboxylic acid is fully formed and purified.

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Key Concepts

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

Carboxylic Acid Synthesis

Carboxylic acids can be synthesized through various methods, including oxidation of alcohols, hydrolysis of nitriles, and carbon chain elongation. Understanding the functional groups and reactivity of starting materials is crucial for determining the appropriate synthetic route. In this case, the transformation of allyl iodide to but-3-enoic acid involves strategic manipulation of carbon skeletons and functional groups.

Allyl Iodide Reactivity

Allyl iodide is a reactive alkyl halide that can undergo nucleophilic substitution and elimination reactions. Its structure allows for the formation of a double bond through elimination, which is essential for synthesizing alkenes. Recognizing how allyl iodide can be transformed into intermediates that lead to the desired carboxylic acid is key to solving the synthesis problem.

Carbon Chain Elongation

Carbon chain elongation involves adding carbon atoms to a molecule, often through reactions like Grignard reactions or alkylation. In the context of synthesizing but-3-enoic acid, understanding how to extend the carbon chain from allyl iodide and subsequently introduce a carboxylic acid functional group is vital. This concept is fundamental in organic synthesis for constructing complex molecules from simpler precursors.

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Related Practice

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

Multiple Choice

Which of the following best describes the carboxylation phase of the Calvin cycle?

Multiple Choice

Determine the major product for the following reaction.

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how the following syntheses could be carried out:

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Show how you would synthesize the following carboxylic acids, using the indicated starting materials.(f) allyl iodide → but-3-enoic acid

Key Concepts

Carboxylic Acid Synthesis

Allyl Iodide Reactivity

Carbon Chain Elongation

Watch next

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(f) allyl iodide → but-3-enoic acid