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esterification of phenols

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Question:

Answers:fatty acids and alcohol esters are easy, they just need: 1. Heat 2. Acid catalyst (often PTSA or sulfuric acid) 2. Vacuum 3. Nitrogen sparge the alcohol group will react with the hydrogen on the fatty acid producing water, if the water is not remove, the bond will be hydrolyzed, which is why the vacuum is required to strip out the formed water.

Question:The reaction is vanillin + acetic anhydride with an acid catalyst. We have to determine the product and I can't figure it out.

Answers:You just esterified the phenol part of the vanillin. see: http://en.wikipedia.org/wiki/Vanillin R-OH + CH3COOOCCH3 --> R-O(O=C)CH3 + CH3COOH where R is the rest of the vanillin molecule.

Question:Im doing esterification. I know an alcohol is more reactive than a phenol, but why exactly? also, why does a phenol require an acylating agent and an alcohol does not? Cheers. 1st answer=best answer

Answers:the OH in alcohol has the electrons density on the oxygen atom high thus it has a delta negative and can attack the delta positive on the carbon of the acid while the oxygen atom in phenol OH has less electron density and thus weaker delta negative due to the resonance phenomenon caused by the aromatic structure and therefore it needs help by alkylating agent that facilitates entry of carbon by increasing negative on the oxygen atom

Question:What other products form in the reaction?

Answers:The reaction of a carboxylic acid halogenide (which is also called acyl halide) with an alcohol/phenol. This reaction is usually very rapid due to the high reactivity of the acyl halide (it is often performed at low temperatures), but for the same reason it tends to be difficult to control, often resulting in a mixture of low purity products and a high percentage of by-products. H3C-COCl + HO-CH2-CH3 H3C-COO-CH2-CH3 + H-Cl