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

14. Synthetic Techniques

Alkynide Alkylation

Organic Chemistry

14. Synthetic Techniques

Alkynide Alkylation

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4:58 minutes

Problem 41c

Textbook Question

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.
(c)

Verified step by step guidance

Step 1: Perform an elimination reaction on the starting molecule (cyclopentylmethyl bromide) to form an alkene. Use a strong base, such as potassium tert-butoxide, to remove the bromine atom and generate cyclopentylmethyl alkene (CH2=CH-cyclopentane).

Step 2: Carry out an ozonolysis reaction on the alkene formed in Step 1. Use ozone (O3) followed by a reducing agent like dimethyl sulfide (DMS) or zinc in acetic acid to cleave the double bond and form two products: formaldehyde (H2C=O) and cyclopentylacetaldehyde.

Step 3: Oxidize the aldehyde group in cyclopentylacetaldehyde to a ketone. Use a mild oxidizing agent such as PCC (pyridinium chlorochromate) or a stronger oxidizing agent like Jones reagent (CrO3/H2SO4) to convert the aldehyde to cyclopentylacetone.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic molecules from simpler ones through a series of chemical reactions. Understanding the synthesis pathway is crucial, as it involves selecting appropriate reagents and conditions to achieve the desired product efficiently. Each step in the synthesis must be carefully planned to minimize the number of reactions while maximizing yield.

Reaction Mechanisms

A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. It provides insight into how reactants transform into products, including the formation and breaking of bonds. Familiarity with common mechanisms, such as nucleophilic substitution or elimination, is essential for predicting the outcomes of synthetic routes.

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 vital for understanding reactivity and guiding synthesis, as different groups can dictate the types of reactions that can occur. For example, carbonyl groups (C=O) are key in many synthesis pathways, including the formation of aldehydes and ketones.

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