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

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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3:51 minutes

Problem 56b

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(b) two different alkenes

Verified step by step guidance

Step 1: Identify the target molecule as a tertiary alcohol (3° alcohol) with the hydroxyl group (-OH) attached to a carbon that is bonded to three other carbon atoms.

Step 2: Recognize that tertiary alcohols can be synthesized via the acid-catalyzed hydration of alkenes or hydroboration-oxidation reactions. The key is to select alkenes that will lead to the correct placement of the hydroxyl group.

Step 3: For the first alkene, consider an alkene where the double bond is between the tertiary carbon (where the -OH group will be attached) and one of its neighboring carbons. Acid-catalyzed hydration will add the -OH group to the more substituted carbon (Markovnikov addition). Example: 1-methylcyclopentene.

Step 4: For the second alkene, consider an alkene where the double bond is between the tertiary carbon and a different neighboring carbon. Hydroboration-oxidation can be used to add the -OH group to the less substituted carbon (anti-Markovnikov addition). Example: 2-methylcyclopentene.

Step 5: Ensure that the reaction conditions are appropriate for each synthesis method. For acid-catalyzed hydration, use H₂SO₄ and water. For hydroboration-oxidation, use BH₃ followed by H₂O₂ and NaOH.

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Key Concepts

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

Alcohol Synthesis

Alcohols can be synthesized through various methods, including hydration of alkenes, reduction of carbonyl compounds, and Grignard reactions. Understanding the mechanisms of these reactions is crucial for determining how to convert alkenes into alcohols effectively.

Alkene Reactivity

Alkenes are reactive due to the presence of a double bond, which can undergo various reactions such as electrophilic addition. The choice of alkene affects the regioselectivity and stereochemistry of the resulting alcohol, making it important to analyze the structure of the alkenes used in synthesis.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry involves the spatial arrangement of atoms in molecules. Both concepts are essential when synthesizing alcohols from alkenes, as they influence the final product's properties and reactivity.

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Related Practice

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

g. H₂O + H₂SO₄

Textbook Question

Propose a mechanism to show how 3,3-dimethylbut-1-ene reacts with dilute aqueous H₂SO₄ to give 2,3-dimethylbutan-2-ol and a small amount of 2,3-dimethylbut-2-ene.

HINT: When predicting products for electrophilic additions, first draw the structure of the carbocation (or other intermediate) that results from electrophilic attack.

Textbook Question

Predict the products of the following hydration reactions.

b. 2-phenylpropene + dilute acid

c. 1-phenylcyclohexene + dilute acid

Textbook Question

Propose mechanisms consistent with the following reactions.

(b)

Textbook Question

When fumarate reacts with D₂O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D₂O?

Textbook Question

Draw a mechanism for the acid-catalyzed conversion of DPP to IPP. How do you know that your mechanism is correct?

Textbook Question

d. Is the reaction of 1-butene with HBr regioselective?

e. Is it stereoselective?

f. Is it stereospecific?

Multiple Choice

Predict the product of the following reaction.

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