Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Which of the following compounds does not give a positive iodoform test, even upon heating?
Options
- ACH ₃ NO 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