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Q.

The increasing order of reactivity of the following compounds towards acid catalyzed dehydration is
(a) CH3-CH2-OH
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(d) CH3-C(CH3)2-OH
Choose the correct answer from the options given below.

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a

(c) < (a) < (b) < (d)

b

(a) < (c) < (d) < (b)

c

(b) < (a) < (c) < (d)

d

(b) < (c) < (a) < (d)

answer is A.

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Detailed Solution

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Order of reactivity of alcohols towards acid catalyst dehydration is 3° > 2° > 1°

a < c < d but option (2) is least because OH group is attached to sp2 hybridised carbon atom and partial bond character develops between C–OH bond.
(1) rate of acid catalysed dehydration reaction  stability of carbocation intermediate formed.

 (a) CH3CH2OHC+H2OH3C+H2 (I) 

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Stability order:
II < I < III < IV
Rate of dehydration reaction:
b < a < c < d

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