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What starting material with these reagents will result in 1. NaNH2 2. CH3CH2BR 3. H2, Lindlar's cat.

What starting material with these reagents will result in 1. NaNH2 2. CH3CH2BR 3. H2, Lindlar's cat.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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## Organic Chemistry Problem: Determining the Starting Material In this exercise, you are given a series of reagents and asked to determine the starting material that will result in the given product. ### Reagents: 1. NaNH₂ 2. CH₃CH₂Br 3. H₂, Lindlar's catalyst ### Product: A compound featuring a benzene ring attached to a two-carbon chain with a double bond (specifically, an alkyne that has been partially hydrogenated to a cis-alkene). ### Question: What starting material with the given reagents will lead to the described product? ### Choices: #### Option A: A benzene ring with an ethyne substituent (phenylacetylene). #### Option B: A benzene ring with a propyl substituent with a triple bond at the end. #### Option C: A benzene ring with a butyl substituent. #### Option D: A benzene ring with an ethyne substituent featuring an attached hydrogen atom (phenylacetylene). ### Diagram Explanation: The diagram consists of the following key elements: - The reagents necessary for the reaction are listed (NaNH₂, CH₃CH₂Br, H₂ with Lindlar's catalyst). - The structure of the desired product is a benzene ring attached to a cis-alkene. - Four potential starting materials are provided in a multiple-choice format: - Option A and D both feature a benzene ring with different alkyne substituents. - Option B contains a triple bond but with a three-carbon chain. - Option C does not contain any triple or double bonds, making it an unlikely candidate. The goal is to determine which of these starting materials, when sequentially reacted with the provided reagents, will yield the final product shown in the question. ### Answering the Question: To reason through the problem, consider the steps involved: 1. **NaNH₂** induces deprotonation and formation of a nucleophilic acetylide ion. 2. **CH₃CH₂Br** reacts with the acetylide ion via an SN2 mechanism, extending the carbon chain. 3. **H₂ with Lindlar's catalyst** selectively hydrogenates alkynes to cis-alkenes. Given this sequence, **Phenylacetylene (benzene ring with an ethyne substituent, Option A or D)** is the starting material that, through these reagents
Transcribed Image Text:## Organic Chemistry Problem: Determining the Starting Material In this exercise, you are given a series of reagents and asked to determine the starting material that will result in the given product. ### Reagents: 1. NaNH₂ 2. CH₃CH₂Br 3. H₂, Lindlar's catalyst ### Product: A compound featuring a benzene ring attached to a two-carbon chain with a double bond (specifically, an alkyne that has been partially hydrogenated to a cis-alkene). ### Question: What starting material with the given reagents will lead to the described product? ### Choices: #### Option A: A benzene ring with an ethyne substituent (phenylacetylene). #### Option B: A benzene ring with a propyl substituent with a triple bond at the end. #### Option C: A benzene ring with a butyl substituent. #### Option D: A benzene ring with an ethyne substituent featuring an attached hydrogen atom (phenylacetylene). ### Diagram Explanation: The diagram consists of the following key elements: - The reagents necessary for the reaction are listed (NaNH₂, CH₃CH₂Br, H₂ with Lindlar's catalyst). - The structure of the desired product is a benzene ring attached to a cis-alkene. - Four potential starting materials are provided in a multiple-choice format: - Option A and D both feature a benzene ring with different alkyne substituents. - Option B contains a triple bond but with a three-carbon chain. - Option C does not contain any triple or double bonds, making it an unlikely candidate. The goal is to determine which of these starting materials, when sequentially reacted with the provided reagents, will yield the final product shown in the question. ### Answering the Question: To reason through the problem, consider the steps involved: 1. **NaNH₂** induces deprotonation and formation of a nucleophilic acetylide ion. 2. **CH₃CH₂Br** reacts with the acetylide ion via an SN2 mechanism, extending the carbon chain. 3. **H₂ with Lindlar's catalyst** selectively hydrogenates alkynes to cis-alkenes. Given this sequence, **Phenylacetylene (benzene ring with an ethyne substituent, Option A or D)** is the starting material that, through these reagents
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