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CHEM

210 [CHAPTER 10: REACTIONS AND SYNTHESIS


Chapter 9: Alcohols, Ethers and Epoxides


Complete the equations for the following reactions. Show all organic products if two or more products form, indicate
the major product. Indicate proper stereochemistry where necessary.

a.

b.

c.

d.

e.

f.

g.


h.

i.

j.

k.

1 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Alcohols, Ethers and Epoxides (continued)
a.

b.

c.


d.

e.

f.

g.

h.


i.

j.

k.

l.



2 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Alcohols, Ethers and Epoxides (continued)
a.

b.

c.

d.

e.

f.

g.

h.

i.


j.

k.

l.

3 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Synthesis Texas Two Step Two Step
a.
1) PBr 3 1) TsCl, pyridine
2) O , DMSO 2) O , DMSO

b.

c.

d.

e.

f.

g.

h.

i. 1) PBr 3
2) O , DMSO

j.

k.

l.

m.

4 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 9: Alkenes
a.

b.

c.

d.

e.


f.

g.

h.

i.

j.

k.

l.

m.

5 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 9: Alkenes (continued)

a.

b.

c.
1) BH 3-THF
2) H 2O2, KOH

d.

Chapter 9: Texas Two-Step Two-Step

a.

b.

c.

d.

e.

6 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 9: Alkynes

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

k.

7 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 9-11: Short Syntheses

a.

b.

c.

d.

e.


f.


g.

h.

i.

j.

k.

l.

8 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

m.

n.

9 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Alcohols, Ethers and Epoxides - KEY
Complete the equations for the following reactions. Show all organic products if two or more products form, indicate
the major product. Indicate proper stereochemistry where necessary.

a.

b.

c.

d.

e.

f.

g.


h.

i.

j.

k.

10 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Alcohols, Ethers and Epoxides (continued) - KEY
a.

b.

c.


d.

e.

f.

g.

h.


i.

j.

k.

l.

11 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Alcohols, Ethers and Epoxides (continued) - KEY
a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

k.

l.

12 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

Chapter 11: Synthesis Texas Two Step Two Step -KEY
a.
1) PBr 3 1) TsCl, pyridine
2) O , DMSO 2) O , DMSO

b.

c.

d.

e.


f.


g.

h.


i. 1) PBr 3
2) O , DMSO

j.

k.

l.

13 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

m.

Chapter 9: Alkenes KEY


a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

k.

l.

14 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

m.

Chapter 9: Alkenes (continued) -KEY



a.

b.

c.
1) BH 3-THF
2) H 2O2, KOH

d.

Chapter 9: Texas Two-Step Two-Step - KEY

a.

b.

c.

d.

15 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

e.

Chapter 9: Alkynes KEY

a.

b.

c.

d.

e.

f.

g.

h.

i.

16 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

j.

k.

Chapter 9-11: Short Syntheses KEY Important! There may be other possible answers that
are correct; see Dr. J. to see if your answer is acceptable.

a.

b.

c.

d.

e.

f.

g.

17 Fall 2016

CHEM 210 [CHAPTER 10: REACTIONS AND SYNTHESIS

h.

i.

j.

k.

l.

m.

n.

18 Fall 2016

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