Erythrogenic acid, C 18 H 26 O 2 , an acetylenic fatty acid turns vivid red on exposure to light. It absorbs 5 equivalents of H 2 in the presence of Pd to give stearic acid, CH 3 (CH 2 ) 16 COOH.Upon ozonolysis it gives formaldehyde, CH 2 O; oxalic acid, HOOCCOOH; azelaic acid, HOOC(CH 2 ) 7 COOH; and an aldehydic acid OHC(CH 2 ) 4 COOH. From these data, two possible structures for Erythrogenic acid are to be given. A way to distinguish these two structures is also to be given. Concept introduction: Both alkenes and alkynes yield alkanes by adsorbing H 2 in the presence of Pd catalyst. Alkynes require two equivalents of H 2 while alkenes require one equivalent of H 2 to give alkanes. Upon ozonolysis a monosubstituted carbon in double bond gives an aldehyde , a carbon in terminal double bond gives formaldehyde and carbons in triple bond yield carboxylic acids as products. To give: Two possible structures for erythrogenic acid from the data provided and a way to distinguish these two structures given.

Question

Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 53AP

Interpretation Introduction

Interpretation:

Erythrogenic acid, C₁₈H₂₆O₂, an acetylenic fatty acid turns vivid red on exposure to light. It absorbs 5 equivalents of H₂ in the presence of Pd to give stearic acid, CH₃(CH₂)₁₆COOH.Upon ozonolysis it gives formaldehyde, CH₂O; oxalic acid, HOOCCOOH; azelaic acid, HOOC(CH₂)₇COOH; and an aldehydic acid OHC(CH₂)₄COOH. From these data, two possible structures for Erythrogenic acid are to be given. A way to distinguish these two structures is also to be given.

Concept introduction:

Both alkenes and alkynes yield alkanes by adsorbing H₂ in the presence of Pd catalyst. Alkynes require two equivalents of H₂ while alkenes require one equivalent of H₂ to give alkanes. Upon ozonolysis a monosubstituted carbon in double bond gives an aldehyde, a carbon in terminal double bond gives formaldehyde and carbons in triple bond yield carboxylic acids as products.

To give:

Two possible structures for erythrogenic acid from the data provided and a way to distinguish these two structures given.

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Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.

10. Trimyristin is obtained from coconut oil. It has molecular formula C45H86O6. On being heated with aqueous sodium hydroxide followed by acidification it was converted to glycerol and tetradecanoic acid as the only products. What is its formula?

Carototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to: give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw possible structures for carototoxin, A, and B. Product B structure H2, Lindlar's Structure of carototoxin H2, Pd/C Product A structure

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 53AP

Interpretation Introduction

Interpretation:

Erythrogenic acid, C₁₈H₂₆O₂, an acetylenic fatty acid turns vivid red on exposure to light. It absorbs 5 equivalents of H₂ in the presence of Pd to give stearic acid, CH₃(CH₂)₁₆COOH.Upon ozonolysis it gives formaldehyde, CH₂O; oxalic acid, HOOCCOOH; azelaic acid, HOOC(CH₂)₇COOH; and an aldehydic acid OHC(CH₂)₄COOH. From these data, two possible structures for Erythrogenic acid are to be given. A way to distinguish these two structures is also to be given.

Concept introduction:

Both alkenes and alkynes yield alkanes by adsorbing H₂ in the presence of Pd catalyst. Alkynes require two equivalents of H₂ while alkenes require one equivalent of H₂ to give alkanes. Upon ozonolysis a monosubstituted carbon in double bond gives an aldehyde, a carbon in terminal double bond gives formaldehyde and carbons in triple bond yield carboxylic acids as products.

To give:

Two possible structures for erythrogenic acid from the data provided and a way to distinguish these two structures given.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 53AP

Interpretation Introduction

Interpretation:

Erythrogenic acid, C₁₈H₂₆O₂, an acetylenic fatty acid turns vivid red on exposure to light. It absorbs 5 equivalents of H₂ in the presence of Pd to give stearic acid, CH₃(CH₂)₁₆COOH.Upon ozonolysis it gives formaldehyde, CH₂O; oxalic acid, HOOCCOOH; azelaic acid, HOOC(CH₂)₇COOH; and an aldehydic acid OHC(CH₂)₄COOH. From these data, two possible structures for Erythrogenic acid are to be given. A way to distinguish these two structures is also to be given.

Concept introduction:

Both alkenes and alkynes yield alkanes by adsorbing H₂ in the presence of Pd catalyst. Alkynes require two equivalents of H₂ while alkenes require one equivalent of H₂ to give alkanes. Upon ozonolysis a monosubstituted carbon in double bond gives an aldehyde, a carbon in terminal double bond gives formaldehyde and carbons in triple bond yield carboxylic acids as products.

To give:

Two possible structures for erythrogenic acid from the data provided and a way to distinguish these two structures given.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 53AP

Interpretation Introduction