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

Alkyne Halogenation

Organic Chemistry

10. Addition Reactions

Alkyne Halogenation

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3:45 minutes

Problem 50d

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄, H₂O and (ii) 1. Hg(OAc)₂, H₂O , 2. NaBH₄
(d)

Verified step by step guidance

Step 1: Analyze the structure of the given alkene. The compound consists of a cyclobutane ring attached to a propene group. The double bond is located in the propene group, making it the reactive site for the reactions.

Step 2: For reaction (i) with H2SO4 and H2O, this is an acid-catalyzed hydration reaction. The double bond will undergo electrophilic addition, where the proton (H⁺) from H2SO4 adds to the less substituted carbon of the double bond (Markovnikov's rule), forming a carbocation intermediate.

Step 3: The carbocation intermediate formed in Step 2 will then react with water (H2O), leading to the formation of an alcohol. The hydroxyl group (-OH) will attach to the more substituted carbon of the original double bond.

Step 4: For reaction (ii) with 1. Hg(OAc)2, H2O and 2. NaBH4, this is an oxymercuration-demercuration reaction. The double bond will react with Hg(OAc)2 in the presence of water, forming a mercurinium ion intermediate. Water will attack the more substituted carbon of the mercurinium ion, leading to the addition of an -OH group.

Step 5: In the second step of reaction (ii), NaBH4 reduces the mercury-containing intermediate, replacing the Hg(OAc) group with a hydrogen atom. The final product will be an alcohol, with the -OH group added to the more substituted carbon of the original double bond (Markovnikov addition).

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Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the case of alkenes reacting with sulfuric acid (H₂SO₄) and water, the double bond acts as a nucleophile, attacking the electrophilic sulfur atom, leading to the formation of carbocations and subsequent products.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of the reaction products, particularly when alkenes react with acids or undergo hydration, guiding the formation of more stable carbocation intermediates.

Hydration Reactions

Hydration reactions involve the addition of water (H₂O) to an alkene, resulting in the formation of alcohols. This can occur through acid-catalyzed mechanisms, such as when alkenes react with H₂SO₄ followed by hydrolysis, or through oxymercuration-demercuration, which provides a more regioselective and stereospecific pathway to alcohols, avoiding carbocation rearrangements.

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Related Practice

Textbook Question

Drawing on what you know about the stereochemistry of alkene addition reactions,

a. write the mechanism for the reaction of 2-butyne with one equivalent of Br₂.

Textbook Question

Drawing on what you know about the stereochemistry of alkene addition reactions,

b. predict the configuration of the product of the reaction.

Textbook Question

Show how hex-1-yne might be converted to

d. 1,1,2,2-tetrabromohexane.

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(b)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (ix) Br₂ (2 equiv.). If you expect two products, show both.

(f)

Textbook Question

In Section 10.8.1, you learned that alkenes react more quickly with electrophiles than do the corresponding alkynes (k_alkene/k_alkyne > 1). Explain why there is a greater disparity in the alkene versus alkyne reactivity in the addition of HBr as compared to the addition of Br₂ [The rate data are not real, but are meant to illustrate a real trend.]

Textbook Question

α-Pinene is a terpene found in pine trees. Starting from geranyl diphosphate (a terpene), draw the arrow-pushing mechanism to produce α-pinene. Assume that an enzyme active site will provide whatever acids and bases you might need.

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄, H₂O and (ii) 1. Hg(OAc)₂, H₂O , 2. NaBH₄

(c)

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Predict the products you would get when the following alkenes react under the following conditions: (i) H2SO4, H2O and (ii) 1. Hg(OAc)2, H2O , 2. NaBH4(d)

Key Concepts

Electrophilic Addition

Markovnikov's Rule

Hydration Reactions

Watch next

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄, H₂O and (ii) 1. Hg(OAc)₂, H₂O , 2. NaBH₄
(d)