A-LevelChemistryOrganic synthesis9701/12 · Feb/Mar 2016 · Q231 Mark

But-2-ene-1,4-diol is converted in two steps through an intermediate X into oxobutanedioic acid. HOCH₂CH=CHCH₂OH but-2-ene-1,4-diol step 1 X step 2 hot, acidified KMnO₄ HO₂CCOCH₂CO₂H oxobutanedioic acid What could be the reagent for step 1 and what is the intermediate X?

Acold, acidified KMnO₄, HOCH₂CH₂CH(OH)CH₂OH

Bhot, acidified K₂Cr₂O₇, HO₂CCH=CHCO₂H

Csteam and concentrated H₂SO₄, HOCH₂CH(OH)CH₂CH₂OH

Dwarm, acidified K₂Cr₂O₇, OHCCH(OH)CH₂CHO

✓ Correct answer

C: steam and concentrated H₂SO₄, HOCH₂CH(OH)CH₂CH₂OH

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Topic: Organic synthesis, A-Level Chemistry (syllabus 9701). Multiple choice, 1 mark.
Source: A-Level Chemistry, Feb/Mar 2016 Paper 1 Variant 2, question 23.

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