Organic Chemistry

878 CHAPTER 20 More About Oxidation–Reduction Reactions

44. Identify A–N:


45. Chromic acid oxidizes 2-propanol six times faster than it oxidizes 2-deuterio-2-propanol. Explain. (Hint:See Section 11.7.)


46. Fill in each box with the appropriate reagent:


47. Show how each of the following compounds could be prepared, using the given starting material:

a. d.

b. e.

c.

48. Upon treatment with ozone followed by work-up with hydrogen peroxide, an alkene forms formic acid and a compound that shows
    three signals (a singlet, a triplet, and a quartet) in its spectrum. Identify the alkene.


49. Which of the following compounds would be more rapidly cleaved by

H

H

OH

H

OH

OH

H

OH

AB

HIO 4?

(^1) H NMR
OH NHCH 3
O
HOCCH 2 CH 2 CH 2 CH 2 CCH 3
OO
CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CCH 2 CH 3
O
HOCCH 2 CH 2 CH 2 CH 2 COH
O OO
CH 3 CH 2 CH
O
CH 3 CH 2 COCH 2 CH 2 CH 3
O
CH 3 C
CH 3
CHCH 2 CH 2 CCH 3

1. 
   


2. 
   

   O
   CH 3 CHCHCH 2 CH 2 CCH 3
   CH 3
   OH O

   
   


3. 
   


4. 
   


5. 
   


6. 
   

   CH^3 CHCCH^2 CH^2 CCH^3
   CH 3

   
   

O O

O

CH 3

CH 3 CH

HO CH 3

CH 3

CH 3 CH

1. CH 3 CCl

O

AlCl 3

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


3. LiAlH 4


4. H 2 O

CH 3 l

excess

K 2 CO 3

RCOOH

O

HCl

H 2 O

∆

NH 3

SOCl 2

Br 2

Ag 2 O

ABC + D

J I H G

KN

E + F

L + M

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