(a) Out of t-butyl alcohol and n-butanol, which one will undergo acid catalyzed dehydration faster and why ?

(b) Carry out the following conversions :

     (i) Phenol to Salicylaldehyde

    (ii) t-butylchloride to t-butyl ethyl ether

     (iii) Propene to Propanol

 

 
 
 
 
 

Answers (1)

(a) Tert-butyl alcohol will undergo acid catalyzed dehydration faster, because it forms more stable 3o carbocation than 1o carbocation.

(b)

(i) Phenol to Salicylaldehyde

(ii) t-butylchloride to t-butyl ethyl ether

(CH_{3})_{3}CCl+ NaOH(aq.)\rightarrow (CH_{3})_{3}COH\overset{Na}{\rightarrow} (CH_{3})_{3}CONa\overset{C_{2}H_{5}Cl }{\rightarrow} (CH_{3})_{3}COC_{2}H_{5}

 

(iii) Propene to Propanol

   CH_{3}CH=CH_{2} \xrightarrow[B_{2}H_{6}]{H_{2}O_{2}/OH^{-}} CH_{3}CH_{2}CH_{2}OH

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