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An ether (A), C5H12O, when heated with excess of hot HI produce two alkyl halides which on hydrolysis form compound (B) and (C), oxidation of (B) gave and acid (D) - Chemistry

Answer in Brief

An ether (A), C5H12O, when heated with excess of hot HI produce two alkyl halides which on hydrolysis form compound (B) and (C), oxidation of (B) gave and acid (D), whereas oxidation of (C) gave a ketone (E). Deduce the structural formula of (A), (B), (C), (D), and (E).

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Solution

i. The ether (A) with molecular formula C5H12O is 

\[\begin{array}{cc}\ce{H3C - CH2 - O - HC -CH3}\\\phantom{............}|\phantom{}\\ \phantom{............}\ce{CH3\phantom{}}\end{array}\]

ii. Reacts with hot HI to produce two alkyl halides as follows:

iii. Oxidation of (B) gives acid

\[\ce{CH3 - CH2 - OH ->[{[O]}] \underset{\text{(D)}}{CH3COOH}}\]

iv. Oxidation of (C) gives ketone

\[\begin{array}{cc}
\ce{CH3 - CH - OH ->[{[O]}] CH3 - C = O}\\
\phantom{...}|\phantom{....................}|\\
\phantom{....}\ce{CH3}\phantom{...........}\ce{(E)}\phantom{...}\ce{CH3}
\end{array}\]

Hence, structural formulae of compounds (A) to (E) are

(A)

  \[\begin{array}{cc}\ce{CH3 - CH2 - O - CH - CH3} \\\phantom{.......................}|\phantom{...........}\\ \phantom{.......................}\ce{CH3\phantom{...........}}\end{array}\]

(2-Ethoxypropane)

(B)

CH3CH2–OH (Ethanol)

(c)

\[\begin{array}{cc}\ce{CH3 - CH - OH}\\|\phantom{}\\ \ce{CH3\phantom{}}\end{array}\] 

(Propan-2-ol)

(D)

CH3COOH (Ethanoic acid)

(E)

\[\begin{array}{cc}
\ce{CH3 - C = O}\\
\phantom{...}|\\
\phantom{...}
\ce{CH3}\end{array}\] 

(Propanone)

  Is there an error in this question or solution?
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APPEARS IN

Balbharati Chemistry 12th Standard HSC Maharashtra State Board
Chapter 11 Alcohols, Phenols and Ethers
Exercise | Q 4 | Page 253
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