Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Concept explainers

Reactive Intermediates
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Hydride Shift
A hydride shift is a rearrangement of a hydrogen atom in a carbocation that occurs to make the molecule more stable. In organic chemistry, rearrangement of the carbocation is very easily seen. This rearrangement can be because of the movement of a carboc…
Vinylic Carbocation
A carbocation where the positive charge is on the alkene carbon is known as the vinyl carbocation or vinyl cation. The empirical formula for vinyl cation is C2H3+. In the vinyl carbocation, the positive charge is on the carbon atom with the double bond t…
Cycloheptatrienyl Cation
It is an aromatic carbocation having a general formula, [C7 H7]+. It is also known as the aromatic tropylium ion. Its name is derived from the molecule tropine, which is a seven membered carbon atom ring. Cycloheptatriene or tropylidene was first synthes…
Stability of Vinyl Carbocation
Carbocations are positively charged carbon atoms. It is also known as a carbonium ion.
Question
**SN1/E1 Carbocation Stability Analysis** In this exercise, you are asked to draw the more stable carbocation for each of the molecules undergoing an SN1/E1 reaction. The stability of a carbocation is crucial in determining the rate of reaction in these mechanisms. Let's examine each molecule: 1. **Top Molecule:** - **Structure:** A branched alkyl structure with a bromide leaving group attached to a secondary carbon. - **Carbocation Formation:** The bromide ion leaves, resulting in a carbocation at the secondary carbon. The stability can be increased if the carbocation is adjacent to a tert-butyl group, allowing hyperconjugation and inductive effects to enhance stability. 2. **Bottom Molecule:** - **Structure:** Another alkyl structure with a bromide leaving group, attached to a tertiary carbon this time. - **Carbocation Formation:** The bromide ion leaves, forming a carbocation at the tertiary carbon, which is inherently more stable than secondary carbocations due to additional hyperconjugation and inductive effects from surrounding methyl groups. **Explanation of Mechanisms:** - **SN1 Reaction:** Involves two steps: formation of the carbocation and nucleophilic attack. The stability of the carbocation is a key factor in reaction rate. - **E1 Reaction:** Also involves two steps: formation of the carbocation followed by elimination. The likelihood of elimination versus substitution often depends on the reaction conditions and the nature of the nucleophile/base. These reactions emphasize the role of carbocation stability, which can be enhanced through molecular structure and neighboring electron-donating groups.
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Transcribed Image Text:**SN1/E1 Carbocation Stability Analysis** In this exercise, you are asked to draw the more stable carbocation for each of the molecules undergoing an SN1/E1 reaction. The stability of a carbocation is crucial in determining the rate of reaction in these mechanisms. Let's examine each molecule: 1. **Top Molecule:** - **Structure:** A branched alkyl structure with a bromide leaving group attached to a secondary carbon. - **Carbocation Formation:** The bromide ion leaves, resulting in a carbocation at the secondary carbon. The stability can be increased if the carbocation is adjacent to a tert-butyl group, allowing hyperconjugation and inductive effects to enhance stability. 2. **Bottom Molecule:** - **Structure:** Another alkyl structure with a bromide leaving group, attached to a tertiary carbon this time. - **Carbocation Formation:** The bromide ion leaves, forming a carbocation at the tertiary carbon, which is inherently more stable than secondary carbocations due to additional hyperconjugation and inductive effects from surrounding methyl groups. **Explanation of Mechanisms:** - **SN1 Reaction:** Involves two steps: formation of the carbocation and nucleophilic attack. The stability of the carbocation is a key factor in reaction rate. - **E1 Reaction:** Also involves two steps: formation of the carbocation followed by elimination. The likelihood of elimination versus substitution often depends on the reaction conditions and the nature of the nucleophile/base. These reactions emphasize the role of carbocation stability, which can be enhanced through molecular structure and neighboring electron-donating groups.
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