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Aldehydes Ketones and Carboxylic Acids question

2011 · Shift 0 · Q8
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Aldehydes Ketones and Carboxylic Acids question

2011 · Shift 0 · Q8

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Trichloroacetaldehyde was subjected to Cannizzaro’s reaction by using NaOH. The mixture of the products contains sodium trichloroacetate and another compound. The other compound is :
  1. A
    Trichloromethanol
  2. B
    2, 2, 2-Trichloropropanol
  3. C
    Chloroform
  4. D
    2, 2, 2-Trichloroethanol
View written solutionFree

Correct answer: D

  1. Identify the substrate

Trichloroacetaldehyde is chloral:

CCl3CHO\text{CCl}_3\text{CHO}CCl3​CHO

It has no α\alphaα-hydrogen, so it undergoes Cannizzaro reaction with strong base.

  1. Recall Cannizzaro reaction

For an aldehyde without α\alphaα-hydrogen:

2 RCHO+OH−→RCOO−+RCH2OH2\,RCHO + OH^- \rightarrow RCOO^- + RCH_2OH2RCHO+OH−→RCOO−+RCH2​OH

One molecule is oxidized to carboxylate, and the other is reduced to alcohol.

For chloral:

2 CCl3CHO+NaOH→CCl3COONa+CCl3CH2OH2\,\text{CCl}_3\text{CHO} + NaOH \rightarrow \text{CCl}_3\text{COONa} + \text{CCl}_3\text{CH}_2\text{OH}2CCl3​CHO+NaOH→CCl3​COONa+CCl3​CH2​OH

So along with sodium trichloroacetate, the other product is:

CCl3CH2OH\text{CCl}_3\text{CH}_2\text{OH}CCl3​CH2​OH

  1. Name the alcohol formed

The structure CCl3CH2OH\text{CCl}_3\text{CH}_2\text{OH}CCl3​CH2​OH is a two-carbon alcohol.

  • Carbon-1: CH2OH\text{CH}_2\text{OH}CH2​OH
  • Carbon-2: CCl3\text{CCl}_3CCl3​

Hence its IUPAC name is:

2,2,2-trichloroethanol\text{2,2,2-trichloroethanol}2,2,2-trichloroethanol

  1. Check options
  • A: Trichloromethanol →\rightarrow→ incorrect
  • B: 2,2,2-Trichloropropanol →\rightarrow→ incorrect (3-carbon alcohol)
  • C: Chloroform →\rightarrow→ incorrect
  • D: 2,2,2-Trichloroethanol →\rightarrow→ correct
  1. Final answer

The other compound formed is 2,2,2-trichloroethanol.

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