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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: lukas.stib on May 15, 2021, 02:16:37 AM

Title: Reactions of esters with HCl to haloalkanes
Post by: lukas.stib on May 15, 2021, 02:16:37 AM

Hello chemists,

on WIKI I found these reactions: esters of carbox. acids + HCl = carbox. acids + haloalkanes, for example HCOOCH2CH2CH3 + HCl = HCOOH + CH3CH2CH2Cl, or CH3COOH + CH3COOCH2CH2CH3 + HCl = CH3COOH + CH3CH2CH2Cl.

When I studied this type of reaction, I always came to the conclusion that the hydrochloric acid is hydrolyzing the ester back to the reactants, but there is no information that these reactions took place, which I did. Can you explain to me how they came to this? How to convert esters to haloalkanes by this reaction?


Thank you, Lukáš S.

Title: Re: Reactions of esters with HCl to haloalkanes
Post by: Meter on May 15, 2021, 05:10:12 AM

Can you link to the original article?

The only way I see this happening is if you react with an excess of HCl under aqueous conditions (to shift the equilibrium to the creation of carboxylic acids + alcohol) and then the -OH is substituted by Cl^-. However, the final step is generally only favorable for tertiary alcohols.

Title: Re: Reactions of esters with HCl to haloalkanes
Post by: lukas.stib on May 15, 2021, 05:18:47 AM

Propyl formate: https://eo.wikipedia.org/wiki/Propila_formiato

Propyl acetate: https://eo.wikipedia.org/wiki/Propila_acetato

Reactions - reaction 6