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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6:08 minutes

Problem 30a,b

Textbook Question

Predict the products formed by periodic acid cleavage of the following diols.
(a) CH₃CH(OH)CH(OH)CH₃
(b)

Verified step by step guidance

Step 1: Understand the reaction mechanism of periodic acid (HIO4) cleavage. Periodic acid selectively cleaves vicinal diols (two hydroxyl groups on adjacent carbons) to form carbonyl compounds (aldehydes or ketones). This occurs via oxidation of the diol, breaking the C-C bond between the hydroxyl-bearing carbons.

Step 2: Analyze compound (a), CH3CH(OH)CH(OH)CH3. This is a vicinal diol with hydroxyl groups on adjacent carbons. Periodic acid will cleave the bond between the two hydroxyl-bearing carbons, resulting in two ketone products. The methyl groups on either side of the diol remain intact.

Step 3: Examine compound (b) from the image. Identify the vicinal diol structure in the molecule. The hydroxyl groups are located on adjacent carbons in the cyclic structure. Periodic acid will cleave the C-C bond between these two carbons, breaking the ring and forming two carbonyl compounds.

Step 4: Predict the products for compound (b). After cleavage, the cyclic structure opens up, and the two carbons that originally bore the hydroxyl groups are converted into carbonyl groups (aldehydes or ketones). The rest of the molecule remains unchanged.

Step 5: Summarize the periodic acid cleavage process for both compounds. For (a), the cleavage results in two ketones. For (b), the cleavage opens the ring and forms two carbonyl compounds. Ensure the products are consistent with the oxidation of vicinal diols.

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Key Concepts

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

Periodic Acid Cleavage

Periodic acid (H5IO6) is a strong oxidizing agent that cleaves vicinal diols (1,2-diols) into carbonyl compounds. The reaction involves the formation of a cyclic periodate intermediate, which subsequently breaks down to yield aldehydes or ketones. Understanding this mechanism is crucial for predicting the products of diol cleavage.

Vicinal Diols

Vicinal diols, also known as glycols, are organic compounds containing two hydroxyl (-OH) groups attached to adjacent carbon atoms. Their structure is essential for the periodic acid cleavage reaction, as the proximity of the hydroxyl groups allows for the formation of the cyclic intermediate that leads to cleavage. Recognizing the structure of the diol is key to predicting the cleavage products.

Product Prediction

Predicting the products of a chemical reaction involves understanding the reactants' structure and the reaction mechanism. In the case of periodic acid cleavage, one must identify the positions of the hydroxyl groups in the diol and apply the cleavage mechanism to determine the resulting carbonyl compounds. This skill is fundamental in organic chemistry for anticipating reaction outcomes.

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Related Practice

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.

a. cyclohexanol

b. 1-methylcyclohexanol

c. cyclopentylmethanol

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(n) sodium ethoxide + 2-methyl-2-bromobutane

(o) octan-1-ol + DMSO + oxalyl chloride

(p) 4-cyclopentylhexan-1-ol + DMP reagent

Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

a. octan-1-ol

b. octan-3-ol

Textbook Question

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

a. chromic acid

b. PCC (pyridinium chlorochromate)

c. sodium hypochlorite/acetic acid

Textbook Question

Predict the product of the oxidation reactions shown.

(a)

Textbook Question

Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.