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

3:05 minutes

Problem 30i

Textbook Question

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
(i)

Verified step by step guidance

Step 1: Begin with cyclooctyne as the starting material. Cyclooctyne is an eight-membered ring containing a triple bond. The triple bond is highly reactive and can undergo addition reactions to introduce functional groups.

Step 2: Perform an oxidative cleavage of the alkyne bond in cyclooctyne using a reagent such as ozone (O₃) followed by reductive workup (e.g., Zn and acetic acid). This will break the triple bond and yield two molecules of carboxylic acids.

Step 3: Extend the carbon chain by performing a series of reactions to introduce additional carbons. For example, use a Grignard reaction or alkylation to add carbon chains to the carboxylic acid groups formed in the previous step.

Step 4: Introduce the hydroxyl group (-OH) on the terminal carbon by using a selective oxidation reaction. For example, use a reagent like PCC (Pyridinium chlorochromate) or Jones reagent to oxidize the alcohol to a ketone or aldehyde, followed by further functionalization.

Step 5: Adjust the positions of the functional groups (hydroxyl and carboxylic acid) through selective reactions such as esterification, hydrolysis, or rearrangement to achieve the final target compound structure as shown in the image.

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.

Cyclooctyne Structure and Reactivity

Cyclooctyne is a cyclic alkyne with a unique structure that influences its reactivity. Its strained ring system allows for various reactions, including cycloadditions and functional group transformations. Understanding its geometry and electronic properties is crucial for predicting how it can be transformed into other compounds.

Synthesis Strategies in Organic Chemistry

Synthesis in organic chemistry involves planning a series of chemical reactions to construct a desired compound from simpler starting materials. Key strategies include functional group interconversions, rearrangements, and the use of protecting groups. Familiarity with these strategies is essential for designing a synthetic pathway from cyclooctyne to the target compounds.

Reaction Mechanisms

Understanding reaction mechanisms is vital for predicting the outcomes of chemical reactions. Mechanisms describe the step-by-step process of how reactants transform into products, including the formation and breaking of bonds. Knowledge of common mechanisms, such as nucleophilic substitutions and electrophilic additions, will aid in determining how to effectively synthesize the desired compounds from cyclooctyne.

Watch next

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

Start learning

Related Videos

Related Practice

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.

Textbook Question

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)

(g) cyclooctane-1,2-dione

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.

(d) 2-methylhex-3-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.

(e) cyclodecyne

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

Show more practices