
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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![**Problem Statement:**
Determine the major product of the following reaction:
\[
\text{Benzene with a triple bond at the end} + \text{NaNH}_2 \rightarrow ? + \text{NH}_3
\]
**Options:**
**a)** A benzene ring with a sodium anion (Na⁺) attached to the triple-bonded carbon in a linear configuration.
**b)** A benzene ring with a sodium anion (Na⁺) attached to an internal carbon forming a cyclic structure with a bridged nitrogen.
**c)** A benzene ring with a nitrogen anion (N⁻) at the end of the triple bond.
**d)** A benzene ring with two sodium ions (Na⁺) attached to two adjacent carbons, forming a charged cyclic structure.
**e)** A benzene ring with a triple bond extension, having a sodium anion (Na⁺) at the end carbon.
In this reaction, sodium amide (NaNH₂) acts as a base, facilitating the removal of a proton to form the corresponding anion that serves as an intermediate. The major product is determined by the stability and favorability of the resulting anions or structures.](https://content.bartleby.com/qna-images/question/20b515c9-5e3a-448e-90a2-ac3b562e1523/037ddd47-0430-4dab-b82e-e68574b8ea7b/mrqygk_thumbnail.jpeg)
Transcribed Image Text:**Problem Statement:**
Determine the major product of the following reaction:
\[
\text{Benzene with a triple bond at the end} + \text{NaNH}_2 \rightarrow ? + \text{NH}_3
\]
**Options:**
**a)** A benzene ring with a sodium anion (Na⁺) attached to the triple-bonded carbon in a linear configuration.
**b)** A benzene ring with a sodium anion (Na⁺) attached to an internal carbon forming a cyclic structure with a bridged nitrogen.
**c)** A benzene ring with a nitrogen anion (N⁻) at the end of the triple bond.
**d)** A benzene ring with two sodium ions (Na⁺) attached to two adjacent carbons, forming a charged cyclic structure.
**e)** A benzene ring with a triple bond extension, having a sodium anion (Na⁺) at the end carbon.
In this reaction, sodium amide (NaNH₂) acts as a base, facilitating the removal of a proton to form the corresponding anion that serves as an intermediate. The major product is determined by the stability and favorability of the resulting anions or structures.
Expert Solution

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Step 1: Explanation
The acidic of terminal hydrogen in hydrocarbons increases in this order:
Alkane < alkene < alkyne
Terminal hydrogen of alkyne is most acidic because of the sp-hybridisation of terminal carbon of alkyne.
Terminal hydrogen of alkyne is highly acidic and that's why it reacts with sodamide to form sodium alkynide.
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