Organic Chemistry

Problems 879

50. Show how cyclohexylacetylene can be converted into each of the following compounds:

a. b.

51. Show how the following compounds could be synthesized. The only carbon-containing reagents that are available for each
    synthesis are shown.

a. c.

b.

52. The catalytic hydrogenation of 0.5 g of a hydrocarbon at 25°C consumed about 200 mL of under 1 atm of pressure. Reaction
    of the hydrocarbon with ozone, followed by treatment with hydrogen peroxide gave one product, which was found to be a four-
    carbon carboxylic acid. Identify the hydrocarbon.


53. Tom Thumbs was asked to prepare the following compounds from the given starting materials. The reagents he chose to use for
    each synthesis are shown.
    a. Which of his syntheses were successful?
    b. What products did he obtain from the other syntheses?
    c. In his unsuccessful syntheses, what reagents should he have used to obtain the desired product?

1.

2.

3.

54. The catalytic hydrogenation of compound A formed compound B. The IR spectrum of compound A and the spectrum of
    compound B are shown. Identify the compounds.

2.5 2.6 2.72.82.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16

4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600

Wavelength (μm)

Wave number (cm−^1 )

% Transmittance

(^1) H NMR

1. RCOOH


2. HO−

H 3 CCH 3

OH

H 3 C

OH

CH 3

O

CH 3 CH 2 COCH 3 CH 3 CH 2 CH 2 OH CH 3 OH

1. NaBH 4


2. H 3 O+

O

+

CH 3

CH 3 CH 2 C

KMnO 4

CHCH (^3) H 2 SO 4
CH 3
OH OH
CH 3 CH 2 C CHCH 3
H 2
CH 3 CHCH 2 CH 2 CH 3
CH 3 CH 3
CH 3 CHOH
CH 3 CHOH
CH 3
OO
CH 3 CH 2 CH 2 CHCH 2 OH CH 3 CH 2 OH +
CH 3
CH 3 CH 2 CH 2 OH
CH 2 COH
O
COH
O
BRUI20_841_882r3 01-04-2003 1:11 PM Page 879