Q19 of 26 Page 1

Give reasons for the following:

(i) Phenol is more acidic than methanol


(ii) The C – O – H bond angle in alcohols is slightly less than the tetrahedral angle (109028’).


(iii) (CH3)3C – O – CH3 on reaction with HI gives (CH3)3 C – I and CH3 – OH as the main products and not (CH3)3C – OH and CH3 – I.


(i) Phenoxide ion is more stabilized than CH3 – O- ion because of resonance:


Thus phenol is more acidic than CH3–OH.


(ii) Due to presence of lone pair on oxygen which causes repulsion, the bond angle in alcohol is slightly less than tetrahedral angle (109.28’)


(iii) Since is more stabilized through +I effect of three methyl group thus (CH3)3 C – I and CH3 – OH formed on treatment of HI with – (CH3)3C – O – CH3


where Me is CH3.


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(ii)



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