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 Hydration

Organic Chemistry

10. Addition Reactions

Alkyne Hydration

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6:14 minutes

Problem 37c

Textbook Question

How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?
c.

Verified step by step guidance

Identify the target compound and determine its functional group(s) and structure. This will help in deciding the synthetic pathway.

Determine the hydrocarbon starting material that has the same number of carbons as the target compound. For example, if the target compound has six carbons, start with a six-carbon hydrocarbon such as hexane or benzene.

Analyze the functional group transformations required to convert the hydrocarbon into the target compound. For instance, if the target compound contains an alcohol group, you may need to perform an oxidation or reduction reaction.

Plan the sequence of reactions needed to introduce the functional groups. For example, if the target compound is a ketone, you might first oxidize an alcohol or perform a Friedel-Crafts acylation.

Consider the reagents and conditions required for each step of the synthesis. For example, use reagents like PCC for oxidation, or Grignard reagents for carbon-carbon bond formation, ensuring the reaction conditions are compatible with the functional groups present.

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Key Concepts

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

Hydrocarbon Structure

Hydrocarbons are organic compounds consisting solely of hydrogen and carbon atoms. Understanding their structure is crucial for synthesis, as the arrangement of these atoms determines the reactivity and properties of the compound. The number of carbon atoms in the hydrocarbon must match the desired product to ensure that all necessary carbon skeletons are available for further functionalization.

Functional Group Transformation

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic synthesis, transforming one functional group into another is a common strategy to create desired compounds. Recognizing how to manipulate these groups is essential for synthesizing complex molecules from simpler hydrocarbons.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants are converted into products. Understanding these mechanisms is vital for predicting the outcomes of chemical reactions and for designing synthetic pathways. Knowledge of mechanisms allows chemists to identify the necessary reagents and conditions to achieve the desired transformations in the synthesis of organic compounds.

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Related Practice

Textbook Question

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or terminal alkynes. Show what the products would be from hydration of each compound.

c. hex-1-yne

Textbook Question

What reagents should be used to carry out the following syntheses?

Textbook Question

For each of the following ketones/aldehydes, indicate whether it is possible to synthesize it from an alkyne as the only compound in good ( > 50%) yield. If so, how would you do it?

(a)

Textbook Question

Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.

e. aqueous H₂SO₄, HgSO₄

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Only one alkyne forms an aldehyde when it undergoes the mercuric-ion-catalyzed addition of water. Identify the alkyne.

Textbook Question

Show how you would accomplish the following synthetic transformations. Show all intermediates.

h. hex-1-yne → hexan-2-one, CH₃COCH₂CH₂CH₂CH₃

Textbook Question

Draw the ketone(s) you would expect to form by reacting the following alkynes under the conditions of oxymercuration: (a) 6-methyloct-1-yne, (b) 1,10-dicyclohexyldec-5-yne, and (c) 5-phenylhex-2-yne.

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How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product? c.

Key Concepts

Hydrocarbon Structure

Functional Group Transformation

Reaction Mechanisms

Watch next

How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?
c.