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Da Mouse
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#1
Report Thread starter 12 years ago
#1
Hiya people. I've been asked to suggest a series of reactions by which ethanol can be converted to CH3CH(OH)COOH.

Could you react ethanol with PCl5 so that a haloalkane is produced and than make a gignard reagent. And then react the gignard reagent with CO2.... I'm not sure how to keep the OH group :s: :confused:

But is everything from what I said so far right? How can I keep the OH group?
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charco
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#2
Report 12 years ago
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its easier than that
1. oxidise to ethanal (Na2Cr2O7/H+ distil)
2. react with HCN to give CH3CH(OH)CN
3. Hydrolyse the nitrile (heat with dil H+) to the acid to get the product.
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oceane
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#3
Report 12 years ago
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You could partially oxidise ethanol to the aldehyde ethanal using conc. H2SO4 and a small amound ot dichromate. Distil the product as it's formed (not reflux) to prevent full oxidation to the carboxylic acid.

Step2: add acidified KCN which will generate HCN in situ. Nucleophilic attack by the CN- ion will give you H3C-C(H)(OH)-CN.

Step 3: refluxing with dilute acid will hydrolise this hydroxynitrile to give you H3C-CH(OH)-COOH i.e the 2-hydroxycarboxylic acid.
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Da Mouse
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#4
Report Thread starter 12 years ago
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I treat things harder than they actually are :s: Thanx guys!
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