Why is trans-cinnamic acid soluble in acetone but insoluble in NaOH?

Expert Solution

Ans. Trans-cinnamic acid is an organic compound. It has a non-polar benzene ring, to which the hydrophobic alkene (C3) with a terminal –COOH group is linked.

Since the molecule has non-polar region, it does not solvate in aqueous solutions under normal conditions. Acetone, being an organic solvent, can solvate trans-cinnamic acid.

# The –COOH group on trans-cinnamic acid can react with NaOH to form respective carboxylate sale as follow-

C8H7COOH + NaOH -----90⁰C----> C8H7COO^-Na⁺ + H2O

If the reaction happens, the resultant product sodium cinnamate becomes soluble in water due to presence of net negative charge on it. The equilibrium also shift to the right and larger amount of the compound can be solvated in aqueous solution of NaOH.

However, the reaction occurs only at 90⁰-95⁰. So, trans-cinnamate becomes soluble in aqueous solution at round 90⁰C. But at room temperature, it’s sparingly soluble in aqueous solutions.

queen_honey_blossom answered 2 years ago

Explain the IMFs for the Following and wether they are soluble, insoluble or partially insoluble: -Acetone...

Explain the IMFs for the Following and wether they are soluble, insoluble or partially insoluble: -Acetone and Butanol, acetone and ethanol, acetone and CCl4, acetone and hexane, acetone and H2O -Butanol and ethanol, butanol and CCl4, butanol and hexane, butanol and H2O -CCl4 and ethanol, CCl4 and hexane, CCl4 and water -Ethanol and hexane, and ethanol and H2O -Hexane and water

For the bromination of trans-cinnamic acid, provide two reasons as to why pyridinium bromide perbromide is...

For the bromination of trans-cinnamic acid, provide two reasons as to why pyridinium bromide perbromide is the brominating agent of choice as opposed to elemental bromine. Convert 16.5 mmol pyridinium bromide perbromide to grams Convert 300 mmol glacial acetic acid to mL.

Is acetone soluble in 1-propanol? Why or why not?

Predict whether the following compounds are soluble or insoluble in water. Soluble Insoluble

Predict whether the following compounds are soluble or insoluble in water. Soluble Insoluble BaSO4 CuCO3 NH4Br AgNO3 CoCl2 PbCl2

Calculate the mass of 10.0 mmol (SS) or 1.00 mmol of trans-cinnamic acid and the theoretical...

Calculate the mass of 10.0 mmol (SS) or 1.00 mmol of trans-cinnamic acid and the theoretical yield of 2,3-dibromo-3-phenylpropanoic acid? m.w of trans-cinnamic acid: 148.2 m.w of 2,3-dibromo-3-phenylpropanoic acid: 308

Prelab to accompany bromination of trans-cinnamic acid (4 pts each) The stoichiometry of the addition is...

Prelab to accompany bromination of trans-cinnamic acid (4 pts each) The stoichiometry of the addition is 1:1, meaning that for every one mole of transcinnamic acid, one mole of Br2 is needed to form the addition product. The Br2 presents as a solution in dichloromethane solvent. This often causes problems for students when calculating stiochiometric equivalents. The bromine solution is 10% Br2 by volume. For instance, 100 mL of solution contains 10 mL of liquid Br2. The density of Br2...

Phenol is soluble in NaOH (aq) and not NaHCO3 (aq) while benzoic acid is soluble in...

Phenol is soluble in NaOH (aq) and not NaHCO3 (aq) while benzoic acid is soluble in both solutions. Explain how a mixture of phenol, benzoic acid, p-nitroaniline and anthracene can be separated by extraction. PLEASE Dont forget to talk about anthracene!

Calculate the mass of 1.00 mmol of trans-cinnamic acid and the theoretical yield of 2,3-dibromo-3-phenylpropanoic acid.

Is sodium hypochlorite insoluble or soluble?

In Stereochemistry of bromine addition to trans-Cinnamic acid lab we acquired a melting point of which...

In Stereochemistry of bromine addition to trans-Cinnamic acid lab we acquired a melting point of which matched erythro 2 3-dibromo-3-phenylpropanoic acid. Why was the product (or products) formed by anti- addition? explain. what evidence in the lab would help with explaining this? thank you!

Question