convert ethanal to 2-chloroetanal
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2-chloroethanol and 1-chloroethanol (which will probably fall apart to acetaldehyde). So, I would go for doing this in two steps.
First, treat ethanol with a strong acid like concentrated phosphoric acid. Under these conditions, ethanol will dehydrate and result in the formation of ethene.
CH3-CH2-OH → CH2=CH2 + H2O
Then, treat the resulting ethene (aka, ethylene) with hypochlorous acid (HOCL) and the product will be 2-chloroethanol as shown below.
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