Why is maleic acid ion more stable than fumaric acid ion?

Maleic acid is cis-butenedioic acid while fumaric acid is trans-butenedioic acid. In maleic acid ion both charges are present on the same sides, so there will be more repulsion between charges while in fumaric acid ion have charges on the opposite sides, so there will be less repulsion and become more stable.

How do fumaric acid and maleic acid differ?

Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid.

Which is more acidic maleic acid or formic acid?

thats why maleic acid is more acidic then fumeric acid…. Formic acid being the strongest acid, acetic acid is about 10 times less acidic in comparison with formic acid.

Which is more stable maleic or fumaric?

Note: The maleic acid or the cis-form of butenedioic acid is less stable than the Fumaric acid or the trans form of butenedioic acid. Maleic acid is soluble in water but Fumaric acid is not soluble in water.

Why is maleic acid more soluble?

Maleic acid is more soluble in water than formic acid because it has stronger intermolecular forces of attraction due to its ability to create more…

Why is the acidity of maleic acid less than that of formic acid?

Maleic acid is cis-butenedioic acid whereas fumaric acid is trans-butenedioic acid. Maleic acid is able to lose ion and it results in the formation of intra-hydrogen bond. Hence, fumaric acid is unable to give hydrogen ions as compared to maleic acid. That is why, maleic acid is a stronger acid than fumaric acid.

Is maleic acid a strong acid?

Maleic acid is a weak diprotic acid that can dissociate stepwise as shown in equations (1) and (2). As the acid is titrated with strong base, the pH changes in a characteristic way giving rise to a 2-step titration curve.

Is maleic acid soluble in water?

Maleic acid forms colorless prismatic crystals having a melting point of 130.5 °C. It exhibits a high solubility in water, amounting to 78.8 g per 100 ml of water at 25 °C and 392.6 g per 100 ml of water at 97.5 °C. Dissolved in water, maleic acid is a very strong organic acid.

Does maleic acid have hydrogen bonding?

Fumaric acid can form intermolecular hydrogen bonds (strong) while maleic acid forms intramolecular hydrogen bonds (weak), hence fumaric acid has higher boiling point than maleic acid.”

Is formic acid more acidic than maleic acid?

Which is more acidic formic or malonic acid?

So, Oxalic acid (COOH-COOH) is more acidic than formic acid (HCOOH). Malonic acid, (COOH−CH2−COOH) is less acidic than oxalic acid because of the intervening presence of −CH2 group and succinic acid (COOH−CH2−CH2−COOH) which is much weaker than (COOH−CH2−COOH).

What does maleic acid react with?

Maleic acid shows reactions typical of both olefins and carboxylic acids. Commercially important reactions of the acid groups include esterification with glycols to polyesters and dehydration to the anhydride.

Why is maleic acid a better conjugate base than fumaric acid?

Maleic acid, being a cis-isomer is capable of forming intra-hydrogen bond after losing H + ion, making the conjugate base much stable than the trans form (fumaric acid) because both the oxygen atoms have strong interaction with the remaining H -atom. Hence, Aand D are the correct options.

Is maleic acid polyprotic or ionic?

Maleic acid and fumaric acid are both polyprotic. They can donate proton twice. With a strong hydrogen bond, the molecule usually exists in this quasi-cycle form. When it deprotonates, it forms a stable anion due to conjugation: Unlike maleic acid, there can be no intramolecular hydrogen bond.

Why does maleic acid form a stable anion after deprotonation?

Unlike maleic acid, there can be no intramolecular hydrogen bond. Hence no stabilized anion. Since after deprotonating the first time, maleic acid forms a stable anion, while fumaric acid cannot, K a 1 [1] of maleic is higher than of fumaric. For the same reason, K a 2 of fumaric acid is higher than of maleic.

What is the melting point of maleic acid?

Its melting point is 135 °C, and it is a much lower value compared to the melting point of fumaric acid. Above this temperature, the compound decomposes. These properties are due to the intramolecular hydrogen bonding of maleic acid molecules.