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
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