(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
OR
(a) Give the mechanism for the formation of ethanol from ethene.
(b) Predict the reagent for carrying out the following conversions:
(i) Phenol to benzoquinone
(ii) Anisole to p-bromoanisole
(iii) Phenol to 2,4,6-tribromophenol

Question

(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
OR
(a) Give the mechanism for the formation of ethanol from ethene.
(b) Predict the reagent for carrying out the following conversions:
(i) Phenol to benzoquinone
(ii) Anisole to p-bromoanisole
(iii) Phenol to 2,4,6-tribromophenol

Accepted Answer

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

(b) (i)
Question Image

(ii)
${({CH}_{3})}_{3} CCl + NaOH (aq .) \to {({CH}_{3})}_{3} COH \overset{Na}{\to} {({CH}_{3})}_{3} CONa \overset{C_{2} H_{5} Cl}{\to} {({CH}_{3})}_{3} {COC}_{2} H_{5}$

(iii)
${CH}_{3} CH = {CH}_{2} \frac{H_{2} O_{2} / {OH}^{-}}{B_{2} H_{6}} {CH}_{3} {CH}_{2} {CH}_{2} OH$

OR

(a) Mechanism for the formation of ethanol from ethene-
Question Image

(b) (i) Phenol to benzoquinone- ${Na}_{2} {Cr}_{2} O_{7} + H_{2} {SO}_{4}$
Question Image
(ii) Anisole to p-Bromo anisole - Br₂ in CH3COOH

(iii) Phenol to 2,4,6-tribromophenol - Br2 aq. / Bromine water
Question Image

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