Organic Chemistry

Problems 877

c.

40. Describe how 1-butyne can be converted into each of the following compounds:

a. b.

41. a. Give the products obtained from ozonolysis of each of the following compounds, followed by work-up under oxidizing
    conditions:

b. What compound would form the following products upon reaction with ozone, followed by work-up under reducing

conditions?

42. Show how each of the following compounds can be prepared from cyclohexene:

a. c.

b. d.

43. The spectrum of the product obtained when an unknown alkene reacts with ozone and the ozonolysis product is worked
    up under oxidizing conditions is shown. Identify the alkene.

10 9 8765 4 3210

(ppm)

frequency

(^1) H NMR
HO
OH
O
O O
O
HO
OH
OH
CH 3
HCCH 2 CH 2 CCH++
OOO
H C H HCH
O
C
OO

H 3 CH

O

H CH 2 CH 3

H 3 CCH 2 CH 3

O

H H

Br

+

OH

+

O

HOCCH 2 CH 2 CH 2 CH 2 COH

OO

BRUI20_841_882r3 01-04-2003 1:11 PM Page 877