Chemistry
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.
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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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