The alcohol shown is warmed with excess iodine and NaOH and the mixture is then acidified. Which structure is the organic acid formed?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The drawn compound is 3-methylbutan-2-ol, a CH3CH(OH)R alcohol. NaOI oxidises it to 3-methylbutan-2-one (C), which is a methyl ketone; the haloform reaction gives CHI3 and 2-methylpropanoate; acidification gives 2-methylpropanoic acid. Structure B has an extra carbon and A is only the trihalo intermediate.

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