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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Which of the following compounds does not give a positive iodoform test, even upon heating?

Options

  1. ACH ₃ NO ₂
  2. BBoth the ester and the dibromo compound

Correct answer

2

Step-by-step solution

The iodoform test is given by compounds containing a CH ₃- CO - group or those that can generate this group under the reaction conditions (alkaline iodine). Compound (1) is a -keto ester containing a CH ₃- CO - group. Upon heating in the alkaline medium, ester hydrolysis and subsequent decarboxylation yield a methyl ketone, which gives a positive iodoform test. Compound (2), CH ₃- C(Br) ₂- CH ₃ , is a gem-dihalide. In the alkaline medium of the iodoform test, it undergoes hydrolysis to form acetone ( CH ₃- CO - CH

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