1. Exam 2 Friday, Oct.,31, 2014 Chapters (which build on1-5) Chem Act 6C, 8, 9,10,11,15,16 Lab Expts 4, 5, 6, 7
For Wednesday’s class 10/29/14 send in any specific problems (text, workbook, lab, etc.,) that you want to discuss in class. by Tues., 10/28/14 at 7:00 pm

2. Chem Act 11 Exercise 4 page 158

3. Chemistry 250-02 Organic Chemistry I Fall, 2014 Day 23,24 10/27,29/14
Organic Chemistry I
Fall, 2014
Day 23,24
10/27,29/14
Chapter 10
Alkyl Halides
Radical Substitution
Chem Act 15A

4. Alkyl Halides Splenda !

5. Some Fluorinated Drugs
Levaquin
Fluticasone
(Veramyst)
Fluoxetine (Prozac)

6. Fluorinated Drugs Of 35 New Drugs Approved in 2011 7 Contain Fluorine

7. How Are Bonds Broken and Made ?

8. The C-X bond can be made from C-H => C-X What Kind of Reaction is This ?

9. Radical Substitution (Lab Expt 8) Chem Activity 15A Models 1-6

10. How many constitutional monochloride isomers will form in the radical-chain chlorination of pentane?3 4 5 6 7

11. How many constitutional monochloride isomers will form in the radical-chain chlorination of 2,3-dimethylpentane? 3 4 5 6 7

12. How many constitutional monobromide isomers will form in the radical-chain bromination of 2,5-dimethylhexane? 3 4 5 6 7

13. Replace H with X in Radical Substitution

14. Radicals

15. Potential Energy of Radicals is like that of C+ Ions
Easier to break
Harder to break

16. Not all C-H bonds are equally reactive Selectivity is 3o > 2o > 1o by 5.0 : 3.5 : 1.0

17. The selectivity of radical chlorination (Cl2/hv) is 1. 0 : 3. 5 : 5
The selectivity of radical chlorination (Cl2/hv) is 1.0 : 3.5 : 5.0 for 1°, 2° and 3° hydrogens, respectively. If only monochlorides form in the radical chlorination of 1,3-dimethylcyclobutane, what is the expected percentage of the tertiary chloride?
1/6 of the total = 17%
1/5 of the total = 20%
1/4 of the total = 25%
1/3 of the total = 33.3%
1/2 of the total = 50%

18. The selectivity of chlorine radical is 1. 0 : 3. 5 : 5
The selectivity of chlorine radical is 1.0 : 3.5 : 5.0 for 1°, 2° and 3° hydrogens, respectively. Assuming that only monochlorides are products in the radical chain chlorination of ,3-dimethybutane, what would be the expected ratio of the two isomeric alkyl chlorides formed in that reaction?
1 to 2
1 to 4
1 to 6
3 to 5
5 to 6

19. Substitute Allylic H’s via Radical Bromination with NBS

20. How Can We Understand This Reaction?

21. What is the major product?B C D E

22. What product(s) is(are) formed?B C D E
B and E
All but A

23. The reaction shown below produces 3 different bromides
The reaction shown below produces 3 different bromides Which of the compounds listed is one of the expected products? 1. 2. 3. 5. 4.

24. Which of the following is not the product of a radical chain-reaction of 2-pentene with NBS?1. 2. 3. 4.

25. What is the product of the following sequence of reactions?1. 2. 3. 4. 5.

27. R-OH -> R-Cl or R-Br

28. Problem 10.21, 10.39

29. What is wrong with these reactions?

30. Problems 10.3 and 10.5 How can you make these molecules ?