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

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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2:08 minutes

Problem 73a

Textbook Question

Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how the following syntheses could be carried out:
a.

Verified step by step guidance

Analyze the target molecule and the starting material to identify the functional groups present and the changes required to convert the starting material into the target molecule. This includes identifying any new bonds formed or broken, as well as any rearrangements or functional group transformations.

Determine the reagents and reactions needed to achieve the required transformations. For example, if a carbon-carbon bond needs to be formed, consider reactions like alkylation, aldol condensation, or Grignard reactions. If a functional group needs to be modified, consider oxidation, reduction, or substitution reactions.

Plan the synthesis step-by-step, ensuring that each intermediate is chemically feasible and that the reagents used are compatible with the functional groups present. For example, if the starting material contains a hydroxyl group, ensure that it is protected if necessary before proceeding with reactions that might affect it.

Verify that the carbon-containing compounds used in the synthesis have no more than two carbons, as per the problem's constraints. For example, you can use compounds like ethylene, acetylene, or formaldehyde as building blocks.

Write out the reaction sequence, including the starting material, intermediates, reagents, and conditions for each step. Ensure that the final product matches the target molecule in structure and stereochemistry.

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Key Concepts

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

Organic Synthesis

Organic synthesis is the process of constructing organic compounds through a series of chemical reactions. It involves the strategic selection of starting materials, reagents, and reaction conditions to achieve the desired product. Understanding the principles of organic synthesis is crucial for designing pathways that efficiently convert simple molecules into more complex structures.

Reagents and Reaction Mechanisms

Reagents are substances used to bring about a chemical reaction, and understanding their roles is essential in organic chemistry. Different reagents can facilitate various types of reactions, such as nucleophilic substitutions or eliminations. Familiarity with reaction mechanisms helps predict the outcome of reactions and the conditions required for successful synthesis.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying functional groups is vital for predicting reactivity and guiding the synthesis process. Knowledge of how different functional groups interact allows chemists to manipulate and transform organic compounds effectively.

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Related Practice

Textbook Question

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(b) (±)-2,7-dimethyloctane-4,5-diol.

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.

(a)

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

Textbook Question

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(a)

Textbook Question

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

(h)

Textbook Question

Show how you would synthesize the following compound. As starting materials, you may use any alcohols containing five or fewer carbon atoms and any necessary solvents and inorganic reagents.

Textbook Question

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(b)

Textbook Question

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(a)

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