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

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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4:33 minutes

Problem 41a,b

Textbook Question

Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?
a. butyric acid
b. isovaleric acid

Verified step by step guidance

Identify the structure of the carboxylic acids given in the problem. Butyric acid is a four-carbon carboxylic acid with the formula CH₃CH₂CH₂COOH, and isovaleric acid is a five-carbon branched carboxylic acid with the formula (CH₃)₂CHCH₂COOH.

Understand the reaction sequence. The reaction involves two steps: (1) substitution of the halide in the alkyl halide with a cyanide group (–CN) using sodium cyanide (NaCN), and (2) hydrolysis of the nitrile group (–CN) in acidic aqueous solution to form a carboxylic acid.

Determine the alkyl halide precursor for butyric acid. The nitrile intermediate for butyric acid is CH₃CH₂CH₂CN. To form this nitrile, the corresponding alkyl halide must be CH₃CH₂CH₂Br or CH₃CH₂CH₂Cl, where the halide group is replaced by –CN in the first step.

Determine the alkyl halide precursor for isovaleric acid. The nitrile intermediate for isovaleric acid is (CH₃)₂CHCH₂CN. To form this nitrile, the corresponding alkyl halide must be (CH₃)₂CHCH₂Br or (CH₃)₂CHCH₂Cl, where the halide group is replaced by –CN in the first step.

Summarize the process: For butyric acid, the alkyl halide is CH₃CH₂CH₂X (where X = Br or Cl). For isovaleric acid, the alkyl halide is (CH₃)₂CHCH₂X (where X = Br or Cl). These alkyl halides undergo substitution with NaCN to form nitriles, followed by hydrolysis to yield the carboxylic acids.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (F, Cl, Br, I). They are important intermediates in organic synthesis and can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile. Understanding the structure and reactivity of alkyl halides is crucial for predicting the products of reactions involving these compounds.

Nucleophilic Substitution Reaction

Nucleophilic substitution reactions involve the replacement of a leaving group (like a halogen) by a nucleophile, such as cyanide ions (CN-). This reaction is fundamental in organic chemistry, particularly in the synthesis of carboxylic acids from alkyl halides. The mechanism can follow either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions of the reaction.

Carboxylic Acid Formation

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). In the context of the question, the reaction of alkyl halides with sodium cyanide followed by hydrolysis in acidic conditions leads to the formation of carboxylic acids. This transformation is significant in organic synthesis, as it allows for the conversion of simpler alkyl halides into more complex carboxylic acids.

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1. acid-catalyzed formation of a hydrate

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(ii) show what compounds would result from complete hydrolysis.

(a)

(b)

(c)

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How could you convert N-methylbenzamide to the following compounds?

b. benzoic acid

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How could you convert N-methylbenzamide to the following compounds?

d. benzyl alcohol

Textbook Question

Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.

Textbook Question

What reagents would you use to convert methyl propanoate to the following compounds?

c. N-ethylpropanamide

d. propanoic acid

Textbook Question

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

Textbook Question

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

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Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution? a. butyric acid b. isovaleric acid

Key Concepts

Alkyl Halides

Nucleophilic Substitution Reaction

Carboxylic Acid Formation

Watch next

Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?
a. butyric acid
b. isovaleric acid