The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed. Concept introduction: Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride. Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl group of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed. Example:

Question

Want to see the full answer?

Answer 1

Question

Chapter 11, Problem 47P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl group of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Example:

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Show work. Don't give Ai generated solution

In the video, we looked at the absorbance of a certain substance and how it varies depending on what wavelength of light we are looking at. Below is a similar scan of a different substance. What color BEST describes how this substance will appear? Absorbance (AU) Violet Blue Green Orange 1.2 1.0- 0.8- 0.6- 0.4- 0.2 0.0 450 500 550 600 650 700 Wavelength (nm) violet indigo blue green yellow orange red Red O Cannot tell from this information In the above graph, what causes -450 nm wavelength of light to have a higher absorbance than light with a -550 nm wavelength? Check all that are true. The distance the light travels is different The different data points are for different substances The concentration is different at different times in the experiment Epsilon (molar absortivity) is different at different wavelengths

5. a. Data were collected for Trial 1 to determine the molar mass of a nonvolatile solid solute when dissolved in cyclo- hexane. Complete the table for the analysis (See Report Sheet). Record calculated values with the correct number of significant figures. B. Freezing Point of Cyclohexane plus Calculation Zone Unknown Solute 2. Mass of cyclohexane (g) 10.14 Part C.4 3. Mass of added solute (g) 0.255 C. Calculations 1. k; for cyclohexane (°C⚫ kg/mol) 20.0 2. Freezing point change, AT, (°C) 3.04 Part C.6 3. Mass of cyclohexane in solution (kg) 4. Moles of solute, total (mol) Show calculation. 5. Mass of solute in solution, total (g) 6. Molar mass of solute (g/mol) Show calculation.