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

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

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10:02 minutes

Problem 43b

Textbook Question

Give the structures of the intermediates represented by letters K and Q in this synthesis.

Verified step by step guidance

Step 1: Analyze the starting material, which is an ester (phenylpropanoate). The first reaction involves LiAlH4 in ether followed by H3O+. This is a reduction reaction that converts the ester into a primary alcohol. The intermediate labeled 'J' is the primary alcohol formed from the reduction of the ester.

Step 2: The alcohol 'J' is treated with TsCl (tosyl chloride) in pyridine. This reaction converts the alcohol into a tosylate, which is a good leaving group. The intermediate labeled 'L' is the tosylate derivative of the alcohol.

Step 3: The tosylate 'L' undergoes elimination with KO-tBu (potassium tert-butoxide), a strong base. This results in the formation of an alkene via an E2 elimination mechanism. The intermediate labeled 'M' is the alkene formed.

Step 4: The alkene 'M' is treated with Br2 followed by H2O. This is a halohydrin formation reaction, where bromine adds across the double bond and water attacks the more substituted carbon. The intermediate labeled 'N' is the halohydrin formed.

Step 5: The halohydrin 'N' is treated with TIPS-Cl (triisopropylsilyl chloride) and Et3N (triethylamine). This reaction protects the hydroxyl group by converting it into a silyl ether. The intermediate labeled 'O' is the silyl-protected halohydrin.

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Key Concepts

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

Synthesis Pathways

Synthesis pathways illustrate the step-by-step transformation of reactants into products through various intermediates. Understanding these pathways is crucial for predicting the structure of intermediates, as each step often involves specific reagents and conditions that dictate the outcome of the reaction. Familiarity with common reactions, such as reductions, oxidations, and substitutions, is essential for interpreting the diagram and identifying the intermediates labeled A to Q.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic synthesis, recognizing functional groups such as alcohols, aldehydes, ketones, and ethers is vital for understanding how intermediates will behave during reactions. The presence of these groups influences reactivity and the types of transformations that can occur, which is key to deducing the structures of intermediates in the synthesis pathway.

Reagents and Conditions

The choice of reagents and reaction conditions significantly affects the course of a chemical reaction and the formation of intermediates. For example, reagents like LiAlH4 are strong reducing agents, while TsCl is used for activating alcohols for substitution reactions. Understanding the role of each reagent and the conditions under which they operate helps in predicting the structures of intermediates and the overall success of the synthesis process.

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Related Practice

Textbook Question

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

d. DMSO and oxalyl chloride

e. DMP (periodinane) reagent

Textbook Question

A chronic alcoholic requires a much larger dose of ethanol as an antidote to methanol poisoning than does a nonalcoholic patient. Suggest a reason why a larger dose of the competitive inhibitor is required for an alcoholic.

Textbook Question

Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.

a. 1-methylcyclopentene

b. 2-methylcyclopentyl tosylate

c. 2-methylcyclopentanone

Textbook Question

Show how you would make each compound, beginning with an alcohol of your choice.

(d)

(e)

(f)

Textbook Question

Predict the major products of the following reactions.

(b)

Textbook Question

Chromic acid oxidation of an alcohol (Section 11-2A) occurs in two steps: formation of the chromate ester, followed by an elimination of H⁺ and chromium. Which step do you expect to be rate-limiting? Careful kinetic studies have shown that Compound A undergoes chromic acid oxidation over 10 times as fast as Compound B. Explain this large difference in rates.

Textbook Question

Predict the major products of the following reactions.

(d)

Textbook Question

Predict the products of the reactions of the following compounds with:

1. chromic acid or excess sodium hypochlorite with acetic acid.

2. PCC or NaOCl (1 equivalent) with TEMPO.

g. hexan-1-ol

h. acetaldehyde, CH₃CHO

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