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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1:47 minutes

Problem 5a

Textbook Question

Explain how 1-butanol can be converted into the following compounds:
a.

Verified step by step guidance

Step 1: Recognize that the target compound is an ester, specifically ethyl butanoate. Esters are typically formed through a reaction between a carboxylic acid and an alcohol in the presence of an acid catalyst.

Step 2: Convert 1-butanol into butanoic acid. This can be achieved by oxidizing 1-butanol using an oxidizing agent such as potassium dichromate (K₂Cr₂O₇) in acidic conditions (H₂SO₄). The primary alcohol is oxidized to a carboxylic acid.

Step 3: Prepare ethanol, which will act as the alcohol component in the esterification reaction. Ethanol is readily available and does not require synthesis in this case.

Step 4: Perform the esterification reaction. Mix butanoic acid and ethanol in the presence of a strong acid catalyst, such as concentrated sulfuric acid (H₂SO₄). Heat the mixture to promote the reaction, which forms ethyl butanoate and water as byproducts.

Step 5: Purify the ester product. Use techniques such as distillation to separate ethyl butanoate from the reaction mixture, ensuring the removal of unreacted starting materials and byproducts.

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Key Concepts

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

Alcohol Functional Group

1-butanol is a primary alcohol, characterized by the presence of a hydroxyl (-OH) group attached to a carbon chain. Understanding the properties of alcohols, including their reactivity and ability to undergo various chemical transformations, is essential for predicting how 1-butanol can be converted into other compounds.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, often converting alcohols into aldehydes, ketones, or carboxylic acids. For 1-butanol, oxidation can lead to the formation of butanal or butanoic acid, depending on the reaction conditions and reagents used.

Substitution Reactions

Substitution reactions occur when an atom or group in a molecule is replaced by another atom or group. In the case of 1-butanol, it can undergo substitution to form alkyl halides through reactions with halogenating agents, which is crucial for synthesizing various organic compounds from the alcohol.

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Related Practice

Textbook Question

Suggest a mechanism for the following reactions.

(a) Substitution:

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃ ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

Explain how 1-butanol can be converted into the following compounds:

Textbook Question

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO⁻.

b. Explain, by showing the mechanisms, why different substitution products are obtained.

Textbook Question

When equivalent amounts of methyl bromide and sodium iodide are dissolved in methanol, the concentration of iodide ion quickly decreases and then slowly returns to its original concentration. Account for this observation.

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the outcome of the reaction shown.

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Explain how 1-butanol can be converted into the following compounds:a.

Key Concepts

Alcohol Functional Group

Oxidation Reactions

Substitution Reactions

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Explain how 1-butanol can be converted into the following compounds:
a.