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The number of members that recommended this message. 0 recommendations  Message 1 of 2 in Discussion 
  (Original Message)Sent: 2/1/2005 5:43 AM
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From: MSN Nickname·Steve·Sent: 2/1/2005 7:13 AM
Here's an outline of what happens:
 
1)  Protonate the alcohol oxygen to form  CH3CH=CHCH2OH2+  and Cl-  (the positive formal charge is on the oxygen)
 
2)  A water molecule leaves as the leaving group, giving an allylic carbocation (which has two resonance structures):
 
           +             +
  CH3CH=CH-CH2    CH3CH-CH=CH2
 
3)  Finally, attack by the chloride ion at the positive carbon in each resonance structure gives each product.
 
 
Steve