Single correct option
2,3-Dimethylbutane-2,3-diol is warmed with conc. to give a ketone . Treating with excess in aqueous and then acidifying the aqueous layer gives a carboxylic acid , along with a yellow solid . and are, respectively,
- A. 3,3-dimethylbutanoic acid and
- B. 2,2-dimethylpropanoic acid and
- C. 2,3-dimethylbutanoic acid and
- D. 2,2-dimethylpropanoic acid and
Show answer and solution
Answer: (D) 2,2-dimethylpropanoic acid and
Step 1 is the pinacol-pinacolone rearrangement. Protonation and loss of water from one tertiary gives a tertiary carbocation next to a carbon bearing and two methyl groups; a methyl shift then gives a protonated ketone, and deprotonation gives pinacolone, (3,3-dimethylbutan-2-one). Step 2 is the haloform reaction, which works for a methyl ketone: the is tri-iodinated, hydroxide attacks the carbonyl and leaves. This produces the carboxylate of and yellow iodoform . Option A has an extra carbon, C has the wrong skeleton, and B names methyl iodide, which is not the yellow solid.
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