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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

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Problem 14c

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.
(c)

Verified step by step guidance

Analyze the given chemical structure. The starting material is a compound with a chlorine atom attached to a carbon chain containing a triple bond. The product is an alcohol with the hydroxyl group (-OH) replacing the chlorine atom.

Recognize that this transformation involves a substitution reaction where the chlorine atom is replaced by a hydroxyl group. This suggests the use of a nucleophilic substitution mechanism.

Identify the appropriate reagent for this substitution. A common reagent for replacing a halogen with a hydroxyl group is aqueous sodium hydroxide (NaOH) or potassium hydroxide (KOH). These reagents provide hydroxide ions (OH⁻) as nucleophiles.

Consider the reaction conditions. The reaction may require heating to facilitate the substitution process, as the bond between the carbon and chlorine is relatively strong.

Ensure that the triple bond in the molecule remains intact during the reaction. The chosen reagent and conditions should not affect the alkyne functional group.

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Key Concepts

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

Alcohol Functional Group

An alcohol is an organic compound characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. Understanding the structure and reactivity of alcohols is crucial for predicting how they can be synthesized or converted from other functional groups.

Reagents for Alcohol Synthesis

Various reagents can be used to convert different organic compounds into alcohols. Common reagents include reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), which can reduce carbonyl compounds (like aldehydes and ketones) to alcohols. Knowing the appropriate reagent for a specific conversion is essential for successful synthesis.

Mechanism of Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, often resulting in the conversion of a carbonyl group to an alcohol. Understanding the mechanism, including the role of nucleophiles and electrophiles, helps in predicting the outcome of the reaction and the conditions required for the conversion.

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Related Practice

Textbook Question

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

e. 1-bromo-2-butene + CH₃O⁻

f. 1-bromo-2-butene + CH₃OH

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.

(a)

Textbook Question

When (R)-(1-bromoethyl)benzene is treated with sodium cyanide, a single enantiomer is produced. However, upon treatment of the same molecule with water, a mixture of two enantiomers is obtained.

(a) Explain these results.

(b) Why is only partial racemization sometimes observed?

Textbook Question

Order the following molecules on the basis of their nucleophilic strength using the pKₐ values of their conjugate acids.

Textbook Question

Predict the product(s) of the following reactions.

(f)

Textbook Question

Predict the product(s) of the following reactions.

(g)

Textbook Question

When trans-4-bromocyclohexanol is treated with base, an intramolecular substitution reaction occurs to give a cyclic ether. This product does not form when cis-4-bromocyclohexanol is reacted under the same conditions. Explain these observations.

Textbook Question

Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?

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Suggest a reagent to carry out each of the following conversions to an alcohol.(c)

Key Concepts

Alcohol Functional Group

Reagents for Alcohol Synthesis

Mechanism of Reduction Reactions

Watch next

Suggest a reagent to carry out each of the following conversions to an alcohol.
(c)