# Diol reagent question

1. Jun 7, 2014

### suitcasespeake

1. The problem statement, all variables and given/known data

But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid.
Hot acidified KMnO4 is added in step 2.

HOCH2CH=CHCH2OH ----> X -----> HO2CCOCH2CO2H

What could be the reagent for step 1 and the intermediate X?

reagent for step 1
X
A cold acidified KMnO4
HOCH2CH2CH(OH)CH2OH ​
B hot acidified KMnO4 O
HCCH(OH)CH2CHO​
C steam and concentrated
H2SO4 HOCH2CH(OH)CH2CH2OH ​
D warm acidified K2Cr2O7
HO2CCH=CHCO2H​

3. The attempt at a solution
I'm aware that an alkene reacts with cold KMnO4 to give a dol and hot KMnO4 to give a dicarboxylic acid but I'm stumped since the first compound is both a diol and alkene. Any help appreciated!

2. Jun 8, 2014

### Saitama

Hi suitcasespeake! Welcome to PF!

I suppose your C option is steam and concentrated $H_2SO_4$, right?

It is easy to solve the problem by eliminating the options. Do you see which options are not possible?