[Snake]

hey guys,

i was doing an experiment on protecting group in lab tried with 4 different type of alcohol

 A 2-bromoethanol 

 B 2-ethoxyethanol 

 C 2-methoxyethanol   

 D 4-chlorobutanol

but then only 2-bromoethanol and 4-chlorobutanol worked.. the 2-ethoxyethanol and 2-methoxyethanol did not work... my freinds tried and the same thing happened.. do any of you guys know why?? please help share your thoughts with me am sooo wanting to find out why.. please help guys

the for protecting the alcohol i used dihydropyran,

the procedure:
i added the alcohol i wanted to protect in a flask then anhydrous DCM and dihydropyran then about 100mg of acidic ion exchange resin and stired the mixutre for 2hours.

if you guys have any links to journals where i can find useful information please post it as well.. THANK YOU GUYS