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

10. Addition Reactions

Alkyne Oxidative Cleavage

Organic Chemistry

10. Addition Reactions

Alkyne Oxidative Cleavage

Previous problemNext problem

5:53 minutes

Problem 11a,b

Textbook Question

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a) oct-4-yne → butanoic acid
(b) trans-cyclodecene → decanedioic acid

Verified step by step guidance

For part (a), oct-4-yne to butanoic acid: Begin by recognizing that oct-4-yne is an alkyne, and oxidative cleavage of alkynes can yield carboxylic acids. Use a strong oxidizing agent such as potassium permanganate (KMnO₄) or ozone (O₃) followed by hydrolysis to cleave the triple bond into two carboxylic acids. The cleavage will produce two molecules of butanoic acid since the alkyne is symmetrically substituted.

For part (a), ensure the reaction conditions are acidic or neutral during the oxidative cleavage to facilitate the formation of carboxylic acids from the intermediate products.

For part (b), trans-cyclodecene to decanedioic acid: Recognize that trans-cyclodecene is a cyclic alkene. Oxidative cleavage of alkenes can yield diacids if the double bond is part of a ring. Use ozone (O₃) followed by hydrogen peroxide (H₂O₂) or KMnO₄ under acidic conditions to cleave the double bond and open the ring, forming decanedioic acid.

For part (b), ensure the reaction conditions are carefully controlled to avoid over-oxidation or side reactions. The oxidative cleavage will break the double bond and introduce carboxylic acid groups at both ends of the resulting open-chain molecule.

Verify the products for both parts by analyzing the structures and ensuring the correct number of carbon atoms and functional groups are present in the final carboxylic acids.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 alkynes and alkenes into carboxylic acids involves specific reactions that introduce the carboxyl group (-COOH) into the molecule.

Alkyne Reactivity

Alkynes, characterized by a carbon-carbon triple bond, can undergo various reactions, including hydrolysis and oxidation. For the synthesis of butanoic acid from oct-4-yne, a key step involves the hydration of the alkyne to form a ketone, which can then be further oxidized to yield the desired carboxylic acid. Understanding the mechanisms of these reactions is essential for predicting the products formed during synthesis.

Cycloalkene Reactions

Cycloalkenes, such as trans-cyclodecene, can participate in reactions that lead to the formation of carboxylic acids. In this case, the ring-opening reaction followed by oxidation can be employed to synthesize decanedioic acid. Familiarity with the behavior of cyclic compounds and their reactivity patterns is important for successfully navigating the synthesis of complex molecules from simpler starting materials.

Watch next

Master General features of alkyne cleavage. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C₈H₁₂.

(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethyl sulfide, gives octanedioic acid, HOOC–(CH₂)₆–COOH. Draw the structure of W.

Textbook Question

Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO4 and (2) warm basic KMnO4, then dilute acid.

(b) hex-2-yne

Textbook Question

Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO₄ and (2) warm basic KMnO₄, then dilute acid.

(a) hex-1-yne

Textbook Question

Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO₄ and (2) warm basic KMnO₄, then dilute acid.

Textbook Question

When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

Textbook Question

Predict the products of reaction of pent-1-yne with the following reagents.

g. cold, dilute KMnO₄

h. warm, concd. KMnO₄, NaOH

i. Na, liquid ammonia

Textbook Question

Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.

(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.

Textbook Question

Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.

(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.(a) oct-4-yne → butanoic acid(b) trans-cyclodecene → decanedioic acid

Key Concepts

Carboxylic Acid Synthesis

Alkyne Reactivity

Cycloalkene Reactions

Watch next

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a) oct-4-yne → butanoic acid
(b) trans-cyclodecene → decanedioic acid