What Reagent for Step 1 and Intermediate X in But-2-ene-1,4-diol Conversion

  • Thread starter suitcasespeake
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In summary: Option A is not possible because the diol is both an alkene and a diol. Option B is not possible because the diol is not an alkene. Option C is not possible because the diol is not a dicarboxylic acid. Therefore, the only option is D. In summary, the diol is converted into a dicarboxylic acid through the intermediate X.
  • #1
suitcasespeake
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Homework Statement



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​

Sorry about the unalignment.

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!
 
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  • #2
suitcasespeake said:

Homework Statement



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​

Sorry about the unalignment.

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!

Hi suitcasespeake! Welcome to PF! :smile:

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?
 

Related to What Reagent for Step 1 and Intermediate X in But-2-ene-1,4-diol Conversion

What is the purpose of using a reagent in the conversion of but-2-ene-1,4-diol?

The reagent is used to facilitate the conversion of but-2-ene-1,4-diol into its desired intermediate product. It acts as a catalyst or reactant in the chemical reaction, helping to speed up the conversion process or provide a necessary component for the reaction to take place.

What factors should be considered when selecting a reagent for this conversion?

The choice of reagent will depend on several factors such as the desired intermediate product, reaction conditions, and cost. Other considerations may include the reagent's stability, toxicity, and compatibility with the starting material and other reaction components.

Can multiple reagents be used in the conversion process?

Yes, it is possible to use multiple reagents in the conversion process. In some cases, a combination of reagents may be necessary to achieve the desired intermediate product. However, careful consideration should be given to the compatibility and potential side reactions between the different reagents.

What are the most commonly used reagents for this type of conversion?

The most commonly used reagents for converting but-2-ene-1,4-diol include strong acids, such as sulfuric acid or hydrochloric acid, and various oxidizing agents, such as potassium permanganate or chromium trioxide. However, the choice of reagents may vary depending on the specific reaction conditions and desired intermediate product.

Are there any safety precautions that should be taken when working with reagents in this conversion?

Yes, it is important to follow proper safety protocols when handling reagents in any chemical reaction. This may include wearing appropriate personal protective equipment, working in a well-ventilated area, and carefully following the instructions for handling and disposing of the reagents. It is also recommended to conduct a risk assessment and have proper emergency procedures in place before starting the conversion process.

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