Organic Chemistry

876 CHAPTER 20 More About Oxidation–Reduction Reactions

k. o.

l. p.

m. q.

n. r.

36. How could each of the following compounds be converted to

a. c.

b. d.

37. Identify A–G:


38. Identify the alkene that would give each of the following products upon ozonolysis followed by treatment with hydrogen peroxide:


39. Fill in each box with the appropriate reagent:

a.

b. CH 3 CH 2 Br CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH

O

2.

1.

CH 3 CH 2 CH CH 2 CH 3 CH 2 CH 2 CH 2 OH CH 3 CH CHCH 3 CH 3 COH

O

2.

1.

f. C

O

HO C

COOH

COOH

+ OH

O

+

O

O

HO

OO

c. OH

e.

CCH 3

+

O

HCOH

O

b. CH 3 CCH 2 CH 2 CH 2 CH 2 CCH 2 CH 3

OO

d. +

O

CH 3 CH 2 COH

O

a. CH 3 CH 2 CH 2 COH +

O

CH 3 CCH 3

O

AB C D EF+ + G

1. CH 3 CCl


2. H 2 O

AlCl 3

O

HO− 1. CH 3 MgBr

2. H 3 O+
   
   
   1. O 3 , – 78 °C
      2. H 2 O 2
   
   
   
   

∆

CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH“CH 2

CH 3 CH 2 CH 2 CH CH 3 CH 2 CH 2 CH 2 Br

O

CH 3 CH 2 CH 2 COH?

O

2. H 2 O 2

CH 1. O^3 , –^78 °C

(^2) 2. (CH 3 ) 2 S

1. O 3 , – 78 °C

HO−, ∆

CH CHCH KMnO^4

(^3) Pt
H 2
HO−, cold
CH KMnO^4
3 CH 2 CH 2 C CCH (^3) 2. H 2 O

1. O 3 , – 78 °C
   2. CH 3 MgBr
   3. H 3 O+
   
   
   1. RCOOH
   
   
   
   

O

Na

CH 3 CH 2 CH 2 C CCH (^3) NH 3 (liq)
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