Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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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:

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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.

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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.

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Ozonolysis of alkynes involves the cleavage of the triple bond, producing carboxylic acids.

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In ozonolysis, each of the triple bonded carbon atoms changes to the carboxyl carbon.

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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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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.
The p-toluenesulfonate derived from (R)-2-octanol and p-toluenesulfonyl chloride was allowed to react with sodium benzenethiolate (C6H5SNa). Give the structure, including stereochemistry and the appropriate R or S descriptor, of the product.
1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.   2. 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.

Chapter 9 Solutions

Organic Chemistry - Standalone book

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