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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1:58 minutes

Problem 50c

Textbook Question

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

Verified step by step guidance

Step 1: Begin with bromocyclohexane as the starting material. Bromocyclohexane contains a bromine atom attached to a cyclohexane ring, making it a good candidate for nucleophilic substitution reactions.

Step 2: Perform a nucleophilic substitution reaction to replace the bromine atom with a cyano group (-CN). Use a cyanide salt such as NaCN or KCN in an appropriate solvent like DMSO. This reaction proceeds via an SN2 mechanism, resulting in cyclohexyl cyanide.

Step 3: Hydrolyze the cyano group (-CN) to a carboxylic acid (-COOH). This can be achieved by heating cyclohexyl cyanide with aqueous acid (e.g., HCl or H2SO4) or a base (e.g., NaOH) followed by acidification. The cyano group undergoes hydrolysis to form cyclohexanecarboxylic acid.

Step 4: Purify the product, cyclohexanecarboxylic acid, using techniques such as recrystallization or distillation, depending on the physical properties of the compound.

Step 5: Confirm the structure of the synthesized compound using spectroscopic methods such as IR (to check for the presence of the carboxylic acid functional group) and NMR (to verify the cyclohexane ring and carboxylic acid substitution).

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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 bromocyclohexane, the bromine atom acts as a leaving group, allowing nucleophiles such as hydroxide ions or carboxylate ions to replace it, leading to the formation of new functional groups.

Carboxylic Acid Formation

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They can be synthesized from alcohols or alkyl halides through oxidation or substitution reactions. In this context, converting bromocyclohexane to a carboxylic acid involves nucleophilic substitution followed by oxidation, which introduces the carboxyl group to the cyclohexane ring.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule to form a new isomer. In the synthesis of the desired carboxylic acid from bromocyclohexane, a rearrangement may be necessary to ensure that the carboxyl group is positioned correctly on the cyclohexane ring. Understanding these reactions is crucial for predicting the outcome of synthetic pathways in organic chemistry.

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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.

(c)

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

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

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

Textbook Question

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

(f) allyl iodide → but-3-enoic 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.

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

Key Concepts

Nucleophilic Substitution

Carboxylic Acid Formation

Rearrangement Reactions

Watch next

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