Advices For Studying Organic Chemistry

2) Ethanol is toxic. In rats the lethal dose of ethanol is 13.7 g/Kg of body weight.

3) Abuse of ethanol is a major drug problem in most countries.

11.3C ETHYLENE GLYCOL

1. Ethylene glycol (HOCH 2 CH 2 OH) has a low molecular weight and a high boiling
   point and is miscible with water ⇒ ethylene glycol is an ideal automobile
   antifreeze.

1. Ethylene glycol is toxic.

11.3D DIETHYL ETHER

1. Diethyl ether is a very low-boiling, highly flammable liquid ⇒ open flames or
   sparks from light switches can cause explosive combustion of mixture of diethyl
   ether and air.


2. Most ethers react slowly with oxygen by a radical process called autooxidation to
   form hydroperoxides and peroxides.

Step 1

R C OR' R C

OR'

+ +

H

H

Step 2

O 2

O O

C + C OR'

OR'

Step 3a

+ +

A hydroperoxide

C OR'

OO OOH

C OR'

H

C OR' C

OR'

or

Step 3b (^) C OR' +
OO
C R'O C O O
OR'
C OR'

3. These hydroperoxides and peroxides, which often accumulate in ethers that have
   been left standing for long periods in contact with air, are dangerously explosive.