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3. Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor. However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to cause skin allergies. Dimethyl maleate is an isomer of dimethyl fumarate. The structures and melting points of these two compounds are given below: Dimethyl fumarate Dimethyl maleate m.p. 102°C m.p. -17°C a. Name the type of isomerism involved. b. Explain why the melting point of dimethyl maleate is lower than that of dimethyl fumarate, c. Deduce, with explanation, which of them will have a higher boiling point. d. Both dimethyl fumarate and dimethyl maleate can be hydrolyzed to their corresponding dicarkexwlic acids, fymarig acid and maleic acid. но OH HO. HO Fumaric acid Maleic acid AH°, = -811 kJ/mol AH°, = -791 kJ/mol i. Explain why the AH° of fymaris acid is more negative than that of maleic acid. ii. Deduce, with explanation, which acid is more soluble in water. ii. Both fumaric acid and maleic acid can undergo dehydration reaction to yield a cyclic ester P. Deduce the structure of P. Both fymaris acid and maleic acid can be prepared by oxidation of alcohol or aldehyde. Let the name of alcohol and aldehyde for production of iv. fumaric acid is P and Q, and the name of alcohol and aldehyde for production of maleic acid is R and S. Draw the bond-line formula of P, Q, R and S.

3. Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor. However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to cause skin allergies. Dimethyl maleate is an isomer of dimethyl fumarate. The structures and melting points of these two compounds are given below: Dimethyl fumarate Dimethyl maleate m.p. 102°C m.p. -17°C a. Name the type of isomerism involved. b. Explain why the melting point of dimethyl maleate is lower than that of dimethyl fumarate, c. Deduce, with explanation, which of them will have a higher boiling point. d. Both dimethyl fumarate and dimethyl maleate can be hydrolyzed to their corresponding dicarkexwlic acids, fymarig acid and maleic acid. но OH HO. HO Fumaric acid Maleic acid AH°, = -811 kJ/mol AH°, = -791 kJ/mol i. Explain why the AH° of fymaris acid is more negative than that of maleic acid. ii. Deduce, with explanation, which acid is more soluble in water. ii. Both fumaric acid and maleic acid can undergo dehydration reaction to yield a cyclic ester P. Deduce the structure of P. Both fymaris acid and maleic acid can be prepared by oxidation of alcohol or aldehyde. Let the name of alcohol and aldehyde for production of iv. fumaric acid is P and Q, and the name of alcohol and aldehyde for production of maleic acid is R and S. Draw the bond-line formula of P, Q, R and S.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.11P
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3. Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor. However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to cause skin allergies. Dimethyl maleate is an isomer of dimethyl fumarate. The structures and melting points of these two compounds are given below: Dimethyl fumarate Dimethyl maleate m.p. 102°C m.p. -17°C a. Name the type of isomerism involved. b. Explain why the melting point of dimethyl maleate is lower than that of dimethyl fumarate, c. Deduce, with explanation, which of them will have a higher boiling point. d. Both dimethyl fumarate and dimethyl maleate can be hydrolyzed to their corresponding dicarkexwlic acids, fymarig acid and maleic acid. но Он но. HO Fumaric acid Maleic acid AH°, = -811 kJ/mol AH°, = -791 kJ/mol i. Explain why the AH° of fymaris acid is more negative than that of maleic acid. ii. Deduce, with explanation, which acid is more soluble in water. i. Both fumaric acid and maleic acid can undergo dehydration reaction to yield a cyclic ester P. Deduce the structure of P. Both fumaric acid and maleic acid can be prepared by oxidation of alcohol or aldehyde. Let the name of alcohol and aldehyde for production of iv. fumaric acid is P and Q, and the name of alcohol and aldehyde for production of maleic acid is R and S. Draw the bond-line formula of P, Q, R and S.
Transcribed Image Text:3. Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor. However, it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to cause skin allergies. Dimethyl maleate is an isomer of dimethyl fumarate. The structures and melting points of these two compounds are given below: Dimethyl fumarate Dimethyl maleate m.p. 102°C m.p. -17°C a. Name the type of isomerism involved. b. Explain why the melting point of dimethyl maleate is lower than that of dimethyl fumarate, c. Deduce, with explanation, which of them will have a higher boiling point. d. Both dimethyl fumarate and dimethyl maleate can be hydrolyzed to their corresponding dicarkexwlic acids, fymarig acid and maleic acid. но Он но. HO Fumaric acid Maleic acid AH°, = -811 kJ/mol AH°, = -791 kJ/mol i. Explain why the AH° of fymaris acid is more negative than that of maleic acid. ii. Deduce, with explanation, which acid is more soluble in water. i. Both fumaric acid and maleic acid can undergo dehydration reaction to yield a cyclic ester P. Deduce the structure of P. Both fumaric acid and maleic acid can be prepared by oxidation of alcohol or aldehyde. Let the name of alcohol and aldehyde for production of iv. fumaric acid is P and Q, and the name of alcohol and aldehyde for production of maleic acid is R and S. Draw the bond-line formula of P, Q, R and S.
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