The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid is to be proposed. Concept introduction: An oxidative cleavage results in formation of C − O bonds in place of C − C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules. Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

Question

5. An unknown hydrocarbon A with the formula CóH12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions and show your reasoning.

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 9.10B, Problem 9.24P

(a)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid is to be proposed.

Concept introduction: An oxidative cleavage results in formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

(b)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid is to be shown.

Concept introduction: The oxidative cleavage results in the formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

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5. An unknown hydrocarbon A with the formula CóH12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions and show your reasoning.

3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.

9. The following picture which illustrates the overlap of 2p orbitals to form the T-bonds of an alkyne clearly shows that the angle of the o-bonds must be (a) 120°, (b) 180°, (c) 109.5°. (d) 60° TT H. TT 10. What is the correct name for the following alkyne? (a) 2-chloro-6-methyl-4-heptyne (b) 6-chloro-2-pethyl-3-heptyne (c) 4-chloro-1-isopropyl-1-pentyne (d) isopropyl 2-chloropropyl acetylene CI 11. Select the structure which corresponds to the name 1-methyl-1,3,5-cyclooctatriene (а) (b) (c) (d)

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 9.10B, Problem 9.24P

(a)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid is to be proposed.

Concept introduction: An oxidative cleavage results in formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

(b)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid is to be shown.

Concept introduction: The oxidative cleavage results in the formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

Expert Solution & Answer

Trending nowThis is a popular solution!

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 9.10B, Problem 9.24P

(a)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid is to be proposed.

Concept introduction: An oxidative cleavage results in formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

(b)

Interpretation Introduction

To determine: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid.

Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid is to be shown.

Concept introduction: The oxidative cleavage results in the formation of C−O bonds in place of C−C bonds. The unknown reactants in the reaction can be found from retro synthesis process. Retro synthesis solves the problems related to the organic reactions and aids in planning of desired molecules.

Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.

Expert Solution & Answer

Trending nowThis is a popular solution!

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 9.10B, Problem 9.24P

(a)

Interpretation Introduction