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

10. Addition Reactions

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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2:55 minutes

Problem 13d

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.
(d)

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Identify the type of alcohol synthesis reaction. Common methods include hydroboration-oxidation, oxymercuration-demercuration, or reduction of carbonyl compounds. Determine which method is being used in this specific reaction.

Analyze the starting material. If the starting material is an alkene, the reaction might involve hydroboration-oxidation or oxymercuration-demercuration. If the starting material is a carbonyl compound (aldehyde or ketone), the reaction might involve reduction using reagents like NaBH₄ or LiAlH₄.

Determine the regioselectivity and stereoselectivity of the reaction. For example, hydroboration-oxidation adds the hydroxyl group (-OH) to the less substituted carbon (anti-Markovnikov), while oxymercuration-demercuration adds it to the more substituted carbon (Markovnikov). Reduction of carbonyl compounds typically forms a primary or secondary alcohol depending on the starting material.

Write the intermediate steps of the reaction mechanism. For example, in hydroboration-oxidation, the alkene reacts with BH₃ to form a trialkylborane intermediate, which is then oxidized with H₂O₂/NaOH to yield the alcohol.

Draw the final product, ensuring that the correct functional group (alcohol) is placed at the appropriate position on the molecule, and confirm the stereochemistry if applicable.

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Key Concepts

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

Alcohol Synthesis

Alcohol synthesis refers to the various chemical reactions and methods used to produce alcohols from different starting materials. Common methods include the reduction of carbonyl compounds, hydration of alkenes, and the reaction of alkyl halides with nucleophiles. Understanding the mechanisms and conditions of these reactions is crucial for predicting the products formed.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It includes the identification of intermediates, transition states, and the sequence of bond-breaking and bond-forming events. Familiarity with mechanisms helps in predicting the outcome of reactions, including the formation of alcohols.

Functional Group Transformation

Functional group transformation involves the conversion of one functional group into another through chemical reactions. In the context of alcohol synthesis, this may include the conversion of alkenes to alcohols via hydration or the reduction of carbonyls. Recognizing how different functional groups can be interconverted is essential for predicting the products of synthesis reactions.

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Related Practice

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃.

(e)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(n)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO₄ 2. NaHSO₃. If there is no reaction, write 'no reaction.'

(a)

Textbook Question

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(b)

Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.

(d)

Textbook Question

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(f)

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