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Alcohols, Phenols, and Ethers — Chemistry STD 12 Science — Question

Rajasthan BoardEnglish MediumSTD 12 ScienceChemistryAlcohols, Phenols, and Ethers4 Marks
Question
Read the passage given below and answer the following questions:
Ethers are readily cleaved by $\ce{HI}$ or $\ce{HBr}$ at $373K$ to form an alcohol and an alkyl halide.
$\text{R}-\text{O}-\text{R}+\text{HX}\xrightarrow{373\text{K}}\text{R}-\text{X}+\text{R}-\text{OH}$
$\text{R}-\text{OH}+\text{HX}\xrightarrow{373\text{K}}\text{R}-\text{X}+\text{H}_2\text{O}$
Mixed ether, containing primary or secondary alkyl group, when heated with hydrogen halide, the lower alkyl group forms halide and higher will form an alcohol. Tertiary alkyl ether when heated with hydrogen halide gives tertiary alkyl halide.
The following questions are multiple choice questions. Choose the most appropriate answer:
  1. Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated $\ce{HI}$?
  1. $\ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{C}-\text{O}- \text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3 $
  2. $\text{CH}_3-\text{CH}-\text{CH}_2-\text{O}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \text{CH}_3$
  3. $\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}_2-\text{O}-\text{CH}_3$
  4. $\text{CH}_3-\text{CH}_2-\text{CH}-\text{O}-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3$
  1. When $\ce{CH_2 = CH - O - CH_2 - CH_3}$ reacts with one mole of $\ce{HI},$ one of the products formed is:
  1. Ethane.
  2. Ethanol.
  3. Iodoethene.
  4. Ethanal.
  1. $\ce{(CH_3)_3COCH_3}$ and $\ce{CH_3OC_2H_5}$ are treated with hydroiodic acid. The fragments obtained after reactions are respectively:
  1. $\ce{(CH_3)_3CI + CH_3OH; CH_3I + C_2H_5OH}$
  2. $\ce{(CH_3)_3CI + CH_3OH; CH_3OH + C_2H_5I}$
  3. $\ce{(CH_3)_3COH + CH_3I; CH_3OH + C_2H_5I}$
  4. $\ce{CH_3I + (CH_3)_3COH; CH_3I + C_2H_5OH}$
  1. Which of the following ether is unlikely to be cleaved by hot cone. $\ce{HBr}$?
✓

Answer

  1. $(a) \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{C}-\text{O}- \text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3 $
$\ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{C}-\text{O}\text{CH}_3+\text{HI}\xrightarrow{\text{S}_\text{N}1}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\ \ \ \ \ \ \ \ \ \ \ \ \ \text{(Hot andconc.)}$
  1. $(b)$

  1. $(d)$ Ethanal.
  1. $(a) \ce{(CH_3)_3CI + CH_3OH; CH_3I + C_2H_5OH}$
When mixed ethers are used, the formation of alkyl iodide depends on the nature of alkyl groups. Methyl iodide is formed when one group is methyl and the other a primary or secondary alkyl group.
Here reaction follows $S_N2$ mechanism and because of the steric effect of the larger group, $I^-$ attacks the smaller $(Me)$ group.
$\text{CH}_3\text{OC}_2\text{H}_5+\text{HI}\rightarrow\text{CH}_3\text{I}+\text{C}_2\text{H}_5\text{OH}$
When the substrate is a methyl $t-$alkyl ether, the products are $\ce{t-RI}$ and $\ce{MeOH}.$
Here, reaction follows $S_N1$ mechanism and formation of products is controlled by the stability of carbocation.
Since carbocation stability order is:
$3^\circ>2^\circ>1^\circ> {\hbox{ CH}}_3,$ therefore alkyl halide is always derived from tert$-$alkyl group.
$\ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ | \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \\\text{CH}_3-\text{C}-\text{O}-\text{CH}_3+\text{HI}\xrightarrow[\text{S}_\text{N}1]{373\text{K}}\text{CH}_3-\text{C}-\text{I}+\text{CH}_3\text{OH}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\ _\text{rert-Butyl methyl ether}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _\text{tert-Butyl iodide} $
  1. $(a)$

Diphenyl ethers are not cleaved by $\ce{HBr}$ or $\ce{HI}.$

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