1. 8. ADDITION REACTIONS Reactions of alkenes and alkynes

2. OBJECTIVES
1. Describe mechanisms for addition reactions of alkenes and alkynes.
2. Predict the structure of the product(s) of addition reactions.

3. REVIEW
S:8.1
Addition Reactions

4. Alkenes are Basic and Nucleophilic

5. ADDITION OF HYDROGEN HALIDES TO ALKENES
Prob:8.29,33
Reaction

6. Mechanism

7. Regiochemistry
Markovnikov’s rule

8. Stability of Carbocations

9. Anti-Markovnikov Addition

10. Stereochemistry of H–Hal Addition to Alkenes

11. HWeb Answer HWeb Answer HWeb27
Question 1. What would be the major organic product from the following reaction?
1. A
2. B
3. C
4. D
HWeb Answer

12. HWeb Answer HWeb Answer HWeb27
Question 2. What would be the major organic product from the following reaction?
1. A
2. B
3. C
4. D
HWeb Answer

13. ACID-CATALYZED HYDRATION OF ALKENES
Prob:8.28
Addition of Sulfuric Acid

14. Addition of Water

15. ADDITION OF BROMINE AND CHLORINE TO ALKENES
Prob:8.41
Overview

16. Stereochemistry

17. Mechanism

18. Formation of Halohydrins

19. Mechanism

20. HWeb Answer HWeb Answer HWeb28
Question 1. The anti addition of bromine leads to the formation of trans 1, dibromo products from cyclic alkenes. Which statement is true concerning this process?
1. The highly electophilic halogen causes anti addition.
2. The formation of the bromonium ion leads to trans addition.
3. The trans product forms in one step because it is more stable.
4. The bromonium ion intermediate is attacked in a SN2 manner by bromide.
HWeb Answer

21. HWeb Answer HWeb Answer HWeb28
Question 2. What would be the major organic product from the following reaction.
1. A
2. B
3. B and C
4. D
HWeb Answer

22. ADDITION OF CARBENES TO ALKENES
I-CH2-I I-CH2-Zn-I

23. Addition to Alkenes

24. OXIDATION OF ALKENES syn Hydroxylation S:8.10,11
Prob:8.27,31,32,35,39,40,46,47
syn Hydroxylation

25. Oxidative Cleavage

26. ADDITION TO ALKYNES Addition of Br2 and Cl2 Addition of H–Hal

27. Oxidative Cleavage

28. HWeb Answer HWeb Answer HWeb29
Question 1. What would be the major organic product from the following reaction?
1. A
2. B
3. C
4. D
HWeb Answer

29. HWeb Answer HWeb Answer HWeb29
Question 2. What would be the major organic product from the following reaction?
1. A
2. B
3. C
4. D
HWeb Answer

30. SYNTHETIC STRATEGIES Add to your chart of organic reactions S:8.15
Prob: ,37
Add to your chart of organic reactions

35. HWeb Answer HWeb Answer HWeb30
Question 1. What is the product of the addition of one mole of bromine to one mole of 2-butyne?
1. E-1,2-dibromo-2-butene
2. E -1,2-dibromo-1-butene
3. E-2,3-dibromo-2-butene
4. Z-2,3-dibromo-2-butene
HWeb Answer

36. HWeb Answer HWeb Answer HWeb30
Question 2. What is the product of the addition of two moles of hydrogen bromide to one mole of 2-butyne?
1. 1,2-dibromobutane
2. 1,4-dibromobutane
3. 2,3-dibromobutane
4. 2,2-dibromobutane
HWeb Answer

37. CHAPTER 8 ON EXAM 4 Types of Questions
- Describe addition reaction mechanisms
- Predict the products of addition reactions
The problems in the book are good examples of the types of problems on the exam.
Preparing for Exam 4:
- Work as many problems as possible.
- Work in groups.
- Do the “Learning Group Problem” at the end of the chapter.
- Work through the practice exam