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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5:23 minutes

Problem 13

Textbook Question

The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.

Verified step by step guidance

Step 1: Begin by identifying the target molecule, (Z)-1-phenylhex-2-en-1-ol. This compound contains a phenyl group attached to a hex-2-en-1-ol backbone with a Z-configuration at the double bond. The starting material is benzaldehyde (PhCHO), which provides the phenyl group.

Step 2: Perform a Wittig reaction to introduce the alkene functionality. React benzaldehyde (PhCHO) with a Wittig reagent, such as hexylidene triphenylphosphorane, to form the hex-2-en-1-al intermediate. Ensure that the reaction conditions favor the Z-configuration of the double bond.

Step 3: Reduce the hex-2-en-1-al intermediate to the corresponding alcohol, hex-2-en-1-ol. Use a mild reducing agent such as sodium borohydride (NaBH₄) to selectively reduce the aldehyde group without affecting the double bond.

Step 4: Verify the stereochemistry of the product to ensure the Z-configuration of the double bond is retained. This can be confirmed using spectroscopic techniques such as NMR or IR.

Step 5: Purify the final product, (Z)-1-phenylhex-2-en-1-ol, using techniques such as column chromatography to remove any impurities and isolate the desired compound.

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Key Concepts

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

Aldol Condensation

Aldol condensation is a key reaction in organic chemistry where two carbonyl compounds, typically aldehydes or ketones, react in the presence of a base to form a β-hydroxy aldehyde or ketone. This reaction is crucial for synthesizing larger molecules and can lead to the formation of enones or enals upon dehydration. In the context of synthesizing (Z)-1-phenylhex-2-en-1-ol, an aldol reaction can be employed to create the necessary carbon skeleton from benzaldehyde.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the synthesis of (Z)-1-phenylhex-2-en-1-ol, understanding stereochemistry is essential to ensure the correct geometric isomer is produced, as the 'Z' configuration indicates specific spatial arrangements of substituents around the double bond. This concept is vital for predicting the properties and reactivity of the synthesized compound.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule, often through the addition of hydrogen or the removal of oxygen. In the synthesis of (Z)-1-phenylhex-2-en-1-ol, a reduction step may be necessary to convert an intermediate carbonyl compound into the corresponding alcohol. Understanding various reducing agents, such as lithium aluminum hydride or sodium borohydride, is important for selecting the appropriate method for achieving the desired product.

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Textbook Question

How can the following compounds be prepared using ethyne as the starting material?

Textbook Question

How could the following compounds be synthesized from acetylene?

c. CH₃CH═CH₂

Textbook Question

How could the following compounds be synthesized from acetylene?

Textbook Question

How could the following compounds be synthesized from acetylene?

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:

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