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Question:
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Place the following alcohols in decreasing order of rate of dehydration with concentrated H2SO4 :
1. CH3CH2CH(OH)CH2CH2CH3
2. (CH3)2C(OH)CH2CH2CH3
3. (CH3)2C(OH)CH(CH3)2
4. CH3CH2CH(OH)CH(CH3)2
5. CH3CH2CH2CH2CH2CH2OH
Options:
1. CH3CH2CH(OH)CH2CH2CH3
2. (CH3)2C(OH)CH2CH2CH3
3. (CH3)2C(OH)CH(CH3)2
4. CH3CH2CH(OH)CH(CH3)2
5. CH3CH2CH2CH2CH2CH2OH
Solution:
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Verified Answer
The correct answer is:
3 > 2 > 4 > 1 > 5
The alcohols (3) and (2) are both 3o, but alcohol (3) gives a more substituted alkene. Alcohol (4) and (1) are both 2o, but alcohol (4) can give a more substituted alkene and alcohol (5) is 1o. Rate of dehydration of alcohols with concentrated H2SO4 follows the order 3o > 2o > 1o.
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