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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enolate Alkylation and Acylation

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4:52 minutes

Problem 79a

Textbook Question

Show how you would accomplish the following multistep conversions. You may use any additional reagents you need.
(a)

Verified step by step guidance

Analyze the starting material and the target molecule to identify the functional groups present in each. Determine the changes that need to occur (e.g., addition, elimination, oxidation, reduction, etc.).

Break the transformation into smaller, manageable steps. For example, if the target molecule requires a functional group that is not present in the starting material, consider introducing it through a reaction such as halogenation, hydroboration, or oxidation.

Select appropriate reagents and reaction conditions for each step. For example, if you need to convert an alcohol to a ketone, you might use an oxidizing agent like PCC (Pyridinium chlorochromate).

Ensure that the sequence of reactions is logical and avoids side reactions. For instance, if a protecting group is needed to prevent unwanted reactions, include it in the sequence and plan for its removal later.

Write out the reaction mechanism for each step to confirm that the proposed reagents and conditions will lead to the desired intermediate or final product. This will help ensure the feasibility of the multistep synthesis.

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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, transition states, and the types of bonds formed or broken. A clear grasp of mechanisms helps predict the outcome of reactions and the conditions required for them.

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 reactivity and determining the appropriate reagents for conversions. Common functional groups include alcohols, amines, and carboxylic acids, each with unique properties and reactivity patterns.

Reagents and Conditions

The choice of reagents and reaction conditions is vital in organic synthesis, as they dictate the course and efficiency of a reaction. Different reagents can facilitate various transformations, such as oxidation, reduction, or substitution. Understanding how to select and apply the right reagents and conditions is key to successfully achieving the desired multistep conversions.

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Related Practice

Textbook Question

Draw the products of the following reactions:

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

Textbook Question

How could you prepare the following compound using a starting material that contains no more than three carbons?

Textbook Question

Draw the products of the following reactions:

Textbook Question

Show how 4-methyl-3-hexanol can be synthesized from 3-pentanone.

Multiple Choice

Determine if the reaction is thermodynamically or kinetically controlled

Textbook Question

The following are all substitution reactions, two of which we study in later chapters. With no knowledge of mechanism, what would you expect the ratio of products to be for each reaction, based on a random statistical distribution?

(a) Replacing a hydrogen (H) with deuterium (D):

Textbook Question

A carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction. (Hint: In the first step, HO^- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formed in the second step; and HO^- is a nucleophile in the third step.)

Textbook Question

How could each of the following compounds be prepared from a ketone and an alkyl halide?

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Show how you would accomplish the following multistep conversions. You may use any additional reagents you need. (a)

Key Concepts

Reaction Mechanisms

Functional Groups

Reagents and Conditions

Watch next

Show how you would accomplish the following multistep conversions. You may use any additional reagents you need.
(a)