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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1:19 minutes

Problem 15b

Textbook Question

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

Verified step by step guidance

Step 1: Identify the target alcohol structure. Analyze the molecular formula and functional groups present in the alcohol to determine its classification (primary, secondary, or tertiary). This will help guide the choice of reagent and reactant.

Step 2: Consider the synthetic pathway. Alcohols can be synthesized through various methods, such as reduction of carbonyl compounds, hydroboration-oxidation of alkenes, or nucleophilic substitution reactions. Select the most appropriate method based on the target alcohol.

Step 3: If the alcohol is primary, consider using a reduction reaction. For example, aldehydes can be reduced to primary alcohols using reagents like sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). Write the general reaction:

R_{CHO} + H \to R_{CH₂OH}

Step 4: If the alcohol is secondary, consider reducing a ketone. Ketones can be reduced to secondary alcohols using similar reagents (NaBH₄ or LiAlH₄). Write the general reaction:

R_{CO} + H \to R_{CHOH}

Step 5: If the alcohol is tertiary, consider alternative methods such as hydroboration-oxidation of alkenes. For example, a tertiary alcohol can be synthesized by reacting an alkene with borane (BH₃) followed by oxidation with hydrogen peroxide (H₂O₂) in basic conditions. Write the general reaction:

R_{CH=CH₂} \to R_{C(OH)R}

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Key Concepts

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

Alcohol Functional Group

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. The position and number of these hydroxyl groups influence the properties and reactivity of the alcohol. Understanding the structure of alcohols is essential for identifying suitable reactants and reagents for their synthesis.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group in a molecule with a nucleophile, which is an electron-rich species. In the context of alcohol synthesis, this often occurs when a halide or other leaving group is replaced by a hydroxyl group. Recognizing the mechanism of these reactions is crucial for proposing appropriate reagents and reactants.

Reagents for Alcohol Synthesis

Common reagents used to synthesize alcohols include Grignard reagents, alkyl halides, and carbonyl compounds. For example, a Grignard reagent can react with a carbonyl compound to form an alcohol. Knowing the reactivity and compatibility of these reagents with various reactants is vital for successfully proposing a synthesis pathway for specific alcohols.

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Related Practice

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(d)

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

Predict the product of each of the following alcohol synthesis reactions.

(d)

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)

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

Key Concepts

Alcohol Functional Group

Nucleophilic Substitution Reactions

Reagents for Alcohol Synthesis

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