The molecular structures for the compounds A through D, which are consistent with the observed transformations, are to be assigned. Concept Introduction: > Alkylation of acetylene takes place in two steps.In the first step, the acetylene is treated with sodium amide, which converts it to its conjugate base. In step two, the acetylide ion reacts with an alkyl halide , forming a new carbon-carbon single bond. A terminal alkyne is formed in this process. > Repeating the alkylation sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative. > Ozonolysis of alkynes involves the cleavage of the triple bond, producing carboxylic acids. > In ozonolysis, each of the triple bonded carbon atoms changes to the carboxyl carbon. > In case of terminal alkynes, one of the products of ozonolysis is carbonic acid, which further dissociates into carbon dioxide and water.

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Answer 1

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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, Problem 28P

Interpretation Introduction

Interpretation:

The molecular structures for the compounds A through D, which are consistent with the observed transformations, are to be assigned.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps.In the first step, the acetylene is treated with sodium amide, which converts it to its conjugate base. In step two, the acetylide ion reacts with an alkyl halide, forming a new carbon-carbon single bond. A terminal alkyne is formed in this process.
>
Repeating the alkylation sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.
>
Ozonolysis of alkynes involves the cleavage of the triple bond, producing carboxylic acids.
>
In ozonolysis, each of the triple bonded carbon atoms changes to the carboxyl carbon.
>
In case of terminal alkynes, one of the products of ozonolysis is carbonic acid, which further dissociates into carbon dioxide and water.

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An optically active compound A, C6H₁0O₂, when dissolved in NaOH solution, consumed 1 equiv of base. On acidification, 2² compound A was slowly regenerated. Treatment of A with LiAlH in ether followed by protonolysis gave an optically inactive compound B that reacted with acetic anhydride to give an acetate diester derivative C. Compound B was oxidized by aqueous chromic acid to ß-methylglutaric acid (3-methylpentanedioic acid), D. Identify compounds A, B, and C; do not specify stereochemistry. (The absolute stereochemical configurations of chiral substances cannot be determined from the data.) Draw compound A. Incorrect s Draw compound B. Incorrect OH

Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.

Compound A has the molecular formula C14H25Br and was obtained by thereaction of sodium acetylide with 1,12-dibromododecane. On treatment ofcompound A with sodium amide, compound B (C14H24) was obtained. Ozonolysisof compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation ofcompound B over Lindlar palladium gave compound C (C14H26), andhydrogenation over platinum gave compound D (C14H28). Further, C yieldedO=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through Dso as to be consistent with the observed transformations.

Answer 2

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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, Problem 28P

Interpretation Introduction

Interpretation:

The molecular structures for the compounds A through D, which are consistent with the observed transformations, are to be assigned.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps.In the first step, the acetylene is treated with sodium amide, which converts it to its conjugate base. In step two, the acetylide ion reacts with an alkyl halide, forming a new carbon-carbon single bond. A terminal alkyne is formed in this process.
>
Repeating the alkylation sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.
>
Ozonolysis of alkynes involves the cleavage of the triple bond, producing carboxylic acids.
>
In ozonolysis, each of the triple bonded carbon atoms changes to the carboxyl carbon.
>
In case of terminal alkynes, one of the products of ozonolysis is carbonic acid, which further dissociates into carbon dioxide and water.

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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, Problem 28P

Interpretation Introduction

Interpretation:

The molecular structures for the compounds A through D, which are consistent with the observed transformations, are to be assigned.

Concept Introduction:
>
Alkylation of acetylene takes place in two steps.In the first step, the acetylene is treated with sodium amide, which converts it to its conjugate base. In step two, the acetylide ion reacts with an alkyl halide, forming a new carbon-carbon single bond. A terminal alkyne is formed in this process.
>
Repeating the alkylation sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.
>
Ozonolysis of alkynes involves the cleavage of the triple bond, producing carboxylic acids.
>
In ozonolysis, each of the triple bonded carbon atoms changes to the carboxyl carbon.
>
In case of terminal alkynes, one of the products of ozonolysis is carbonic acid, which further dissociates into carbon dioxide and water.

Expert Solution & Answer

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Check out a sample textbook solution

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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, Problem 28P

Interpretation Introduction