What is/are the major isolated organic product(s) of this series of reactions? 1. NaNH2 2. CH3BR 3. HBr (2 eq) Br Br Br A. D. Br Br E. more than one of these Br Br Br B. C.
What is/are the major isolated organic product(s) of this series of reactions? 1. NaNH2 2. CH3BR 3. HBr (2 eq) Br Br Br A. D. Br Br E. more than one of these Br Br Br B. C.
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
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![**Organic Chemistry Reaction Products: Multiple Choice Question**
**Question:**
What is/are the major isolated organic product(s) of this series of reactions?
\[ \text{1. NaNH}_2 \]
\[ \text{2. CH}_3\text{Br} \]
\[ \text{3. HBr (2 eq)} \]
**Answer Choices:**
A. Structure with two bromine atoms on the same carbon.
--)
B. Structure with two bromine atoms on adjacent carbons.
)
C. Structure with two bromine atoms on opposite ends of a three-carbon chain.
)
D. Structure with two bromine atoms attached to a central chiral carbon.
)
E. More than one of these.
**Explanation:**
- The first step involves the reaction of a compound with sodium amide (NaNH₂), a strong base, which often leads to the formation of a reactive intermediate, such as an alkyne.
- The second step involves the alkylation of the intermediate with methyl bromide (CH₃Br), indicating that the intermediate will undergo substitution to add the methyl group.
- The third step involves the reaction with hydrobromic acid (HBr), twice, suggesting that the product will be brominated.
Please analyze the structures provided and determine which one(s) match the expected reaction products based on standard organic chemistry knowledge.
**Graph/Diagram Explanation:**
- There is no graph or complex diagram, but the provided choices are structural formulas of organic compounds with bromine atoms in different positions, as detailed above. The answer relies on understanding the outcomes of reactions with NaNH₂, CH₃Br, and HBr.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F721d873f-4e0f-4b0d-ad64-d3413c60c73c%2F8473c14e-37f1-4556-9e02-791f0ad989f7%2Fthpqvmg_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Organic Chemistry Reaction Products: Multiple Choice Question**
**Question:**
What is/are the major isolated organic product(s) of this series of reactions?
\[ \text{1. NaNH}_2 \]
\[ \text{2. CH}_3\text{Br} \]
\[ \text{3. HBr (2 eq)} \]
**Answer Choices:**
A. Structure with two bromine atoms on the same carbon.
--)
B. Structure with two bromine atoms on adjacent carbons.
)
C. Structure with two bromine atoms on opposite ends of a three-carbon chain.
)
D. Structure with two bromine atoms attached to a central chiral carbon.
)
E. More than one of these.
**Explanation:**
- The first step involves the reaction of a compound with sodium amide (NaNH₂), a strong base, which often leads to the formation of a reactive intermediate, such as an alkyne.
- The second step involves the alkylation of the intermediate with methyl bromide (CH₃Br), indicating that the intermediate will undergo substitution to add the methyl group.
- The third step involves the reaction with hydrobromic acid (HBr), twice, suggesting that the product will be brominated.
Please analyze the structures provided and determine which one(s) match the expected reaction products based on standard organic chemistry knowledge.
**Graph/Diagram Explanation:**
- There is no graph or complex diagram, but the provided choices are structural formulas of organic compounds with bromine atoms in different positions, as detailed above. The answer relies on understanding the outcomes of reactions with NaNH₂, CH₃Br, and HBr.
![**Which is a tautomer of 3-pentanone?**
3-pentanone:
[Diagram of 3-pentanone structure with a carbonyl group (C=O) at the 3rd carbon of a pentane chain]
A. ![Image of the structure with a positively charged oxygen and a hydrogen attached]
\[Diagram showing a molecule with a structure where the oxygen has a positive charge (+) and there is a hydrogen atom (H) attached to it. The carbon chain remains similar to 3-pentanone.\]
B. ![Image of an enol form]
\[Diagram showing a molecule with a hydroxyl group (OH) attached to the second carbon and a double bond between the second and third carbons, representing an enol form.\]
C. ![Image of the structure with a positively charged carbonyl and a negatively charged oxygen]
\[Diagram showing a molecule with a structure where the original carbonyl group now has a positive charge (+) on the carbon and a negative charge (-) on the oxygen, implying resonance forms.\]
D. Two of them
\[Option indicating that more than one of the given structures might be tautomers of 3-pentanone.\]
---
**Explanation:**
The task is to identify tautomers of 3-pentanone from the given chemical structures. Tautomers are isomers of a compound which differ mainly in the placement of a proton and the double bond. There are two common types of tautomers:
- Keto-enol tautomers
- Protonation/deprotonation states
Option B in the provided list represents the enol form of 3-pentanone, which is a tautomer of ketones. The spaces labeled A and C show different ionic forms, which are less likely to represent typical tautomers as per common chemical knowledge.
Therefore, the correct answer from the given selections is B, which shows the enol form of 3-pentanone.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F721d873f-4e0f-4b0d-ad64-d3413c60c73c%2F8473c14e-37f1-4556-9e02-791f0ad989f7%2F5zapgyc_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Which is a tautomer of 3-pentanone?**
3-pentanone:
[Diagram of 3-pentanone structure with a carbonyl group (C=O) at the 3rd carbon of a pentane chain]
A. ![Image of the structure with a positively charged oxygen and a hydrogen attached]
\[Diagram showing a molecule with a structure where the oxygen has a positive charge (+) and there is a hydrogen atom (H) attached to it. The carbon chain remains similar to 3-pentanone.\]
B. ![Image of an enol form]
\[Diagram showing a molecule with a hydroxyl group (OH) attached to the second carbon and a double bond between the second and third carbons, representing an enol form.\]
C. ![Image of the structure with a positively charged carbonyl and a negatively charged oxygen]
\[Diagram showing a molecule with a structure where the original carbonyl group now has a positive charge (+) on the carbon and a negative charge (-) on the oxygen, implying resonance forms.\]
D. Two of them
\[Option indicating that more than one of the given structures might be tautomers of 3-pentanone.\]
---
**Explanation:**
The task is to identify tautomers of 3-pentanone from the given chemical structures. Tautomers are isomers of a compound which differ mainly in the placement of a proton and the double bond. There are two common types of tautomers:
- Keto-enol tautomers
- Protonation/deprotonation states
Option B in the provided list represents the enol form of 3-pentanone, which is a tautomer of ketones. The spaces labeled A and C show different ionic forms, which are less likely to represent typical tautomers as per common chemical knowledge.
Therefore, the correct answer from the given selections is B, which shows the enol form of 3-pentanone.
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