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

9. Alkenes and Alkynes

Alkynide Synthesis

Organic Chemistry

9. Alkenes and Alkynes

Alkynide Synthesis

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3:41 minutes

Problem 51f,g

Textbook Question

Propose structures for intermediates and products (F) through (G)

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Step 1: Analyze the reaction sequence starting with 1-bromobutane. The first reaction involves KOH and H2O, which typically leads to elimination to form an alkene. This step produces intermediate (A), likely 1-butene.

Step 2: Intermediate (A) reacts with sodium (Na), which is a strong reducing agent. This step likely forms a carbanion or a radical intermediate (B).

Step 3: Intermediate (B) reacts with ethyl bromide (CH3CH2Br) in an SN2 reaction, leading to the formation of intermediate (C), which is likely a longer-chain alkane (pentane).

Step 4: The reaction with Mg and ether converts 1-bromobutane into a Grignard reagent (D). This reagent reacts with CH3(CH2)3CHO in the presence of H3O+ to form intermediate (E), likely an alcohol.

Step 5: Intermediate (E) undergoes dehydration with H2SO4 and heat to form an alkene. This alkene is subjected to ozonolysis (O3, -78°C, followed by (CH3)2S), leading to cleavage and formation of aldehydes (F). Subsequent reactions involve bromination, elimination, and hydroboration-oxidation to form intermediates (G) through (K).

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, which are transient species formed during the reaction. A clear grasp of mechanisms helps predict the structure of intermediates and products based on the starting materials and the type of reaction occurring.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting the behavior of organic compounds during reactions, as they dictate reactivity, polarity, and the types of intermediates that may form. This knowledge is vital for proposing accurate structures for intermediates and products.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical properties and reactions. It is important to consider stereochemical factors when proposing structures for intermediates and products, as different stereoisomers can lead to different reactivity and product outcomes. Understanding concepts like chirality and conformational analysis is key to accurately representing molecular structures.

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Related Practice

Textbook Question

Show how you would convert

d. but-1-yne to cis-hex-3-ene.

Textbook Question

Show how you would synthesize the following compounds from acetylene and any other needed reagents:

(a) 6-phenylhex-1-en-4-yne

(b) cis-1-phenylpent-2-ene

Textbook Question

Muscalure, the sex attractant of the common housefly, is cis-tricos-9-ene. Most syntheses of alkenes give the more stable trans isomer as the major product. Devise a synthesis of muscalure from acetylene and other compounds of your choice. Your synthesis must give specifically the cis isomer of muscalure.

Textbook Question

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

Textbook Question

Beginning with acetylene and benzyl bromide and using any other inorganic reagents, propose a synthesis of the alkene shown here.

Textbook Question

Show how the following compounds can be synthesized starting with ethyne:

a. cis-2-octene

Textbook Question

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

e. 2,2-dibromohexane → hex-1-yne

Textbook Question

How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?

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