A-LevelChemistryOrganic synthesis9701/12 · Oct/Nov 2012 · Q241 Mark

But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid. [Figure 24.1] What could be the reagent for step 1 and the intermediate X?

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Areagent for step 1: cold acidified KMnO4, X: HOCH2CH2CH(OH)CH2OH

Breagent for step 1: hot acidified KMnO4, X: OHCCH(OH)CH2CHO

Creagent for step 1: steam and concentrated H2SO4, X: HOCH2CH(OH)CH2CH2OH

Dreagent for step 1: warm acidified K2Cr2O7, X: HO2CCH=CHCO2H

✓ Correct answer

C: reagent for step 1: steam and concentrated H2SO4, X: HOCH2CH(OH)CH2CH2OH

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Topic: Organic synthesis, A-Level Chemistry (syllabus 9701). Multiple choice, 1 mark.
Source: A-Level Chemistry, Oct/Nov 2012 Paper 1 Variant 2, question 24.

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