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Magazine Chapter 7: Problem 11
What products do you expect from the reaction of bromocyclohexane with hydroxide ion?
Short Answer
Expert verified
The major product is cyclohexene, and the minor product is cyclohexanol.
Step by step solution
01
Identify the Reactants
The reactants in this reaction are bromocyclohexane and the hydroxide ion (OH鈦�). Bromocyclohexane is a cyclohexane ring with a bromine atom attached.
02
Analyze Possible Mechanisms
Bromocyclohexane can undergo bimolecular nucleophilic substitution (SN2) or elimination (E2) reactions with hydroxide ion. Since OH鈦� is a strong base and nucleophile, both pathways are plausible.
03
Consider SN2 Mechanism
In an SN2 reaction, the OH鈦� ion would attack the carbon atom bonded to the bromine from the opposite side, leading to the displacement of the bromine atom. This results in the formation of cyclohexanol.
04
Consider E2 Mechanism
In an E2 reaction, the OH鈦� ion would abstract a proton from a 尾-carbon, resulting in the elimination of the bromine atom and formation of a double bond. This forms cyclohexene as a product.
05
Determine Major and Minor Products
Both cyclohexanol (from SN2) and cyclohexene (from E2) can be formed. However, due to steric hindrance, the E2 mechanism is more favorable here, making cyclohexene the major product.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
SN2 mechanism
The SN2 mechanism stands for bimolecular nucleophilic substitution. It involves a single step where the nucleophile attacks from the opposite side of the leaving group, causing the inversion of the molecule's configuration. In the case of bromocyclohexane reacting with hydroxide ion (OH鈦�), the OH鈦� acts as a nucleophile. It attacks the carbon atom bonded to the bromine, pushing the bromine out and forming cyclohexanol. It's important to note that for the SN2 mechanism, the reaction happens in one concerted step without any intermediates. Factors like steric hindrance can impact the rate and feasibility of SN2 reactions.
E2 mechanism
The E2 mechanism stands for bimolecular elimination. Unlike SN2, the E2 reaction involves the base abstracting a proton from the 尾-carbon. The leaving group (bromine in this case) leaves simultaneously, forming a new double bond. For the bromocyclohexane and hydroxide ion reaction, OH鈦� abstracts a 尾-proton, leading to the formation of cyclohexene. This reaction proceeds in one concerted step, and steric hindrance, as well as the strength of the base, can make the E2 mechanism more favorable than the SN2 mechanism. The formation of a double bond in the product (cyclohexene) is a key characteristic of E2 reactions.
cyclohexanol
Cyclohexanol is a product formed through the SN2 reaction mechanism when bromocyclohexane reacts with the hydroxide ion. In this process, the hydroxide ion attacks the carbon attached to the bromine, displacing the bromine atom and forming an alcohol functional group. Cyclohexanol is a secondary alcohol, characterized by a hydroxy group (-OH) attached to a saturated cyclohexane ring. This reaction highlights nucleophilic substitution where the bromine (a leaving group) is replaced by the hydroxide ion (a nucleophile). Cyclohexanol is less likely to form under conditions that favor elimination (E2) reactions due to steric hindrance.
cyclohexene
Cyclohexene is formed through the E2 mechanism when bromocyclohexane reacts with the hydroxide ion. During this process, the hydroxide ion abstracts a proton from a 尾-carbon adjacent to the carbon bonded to bromine. This results in the elimination of the bromine ion and the formation of a double bond, creating cyclohexene. Cyclohexene is a type of alkene, characterized by a double bond within a six-membered carbon ring. Due to steric hindrance around the bromine in bromocyclohexane, the E2 mechanism, leading to cyclohexene, is often favored over the SN2 mechanism.
nucleophilic substitution
Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. For bromocyclohexane reacting with hydroxide ion, the nucleophile (OH鈦�) attacks the carbon attached to the leaving group (bromine) and replaces it. This process can occur via different mechanisms, such as SN2 or SN1. In the case of bromocyclohexane and OH鈦�, the SN2 mechanism is a consideration where the reaction proceeds through a single, concerted step with the nucleophile attacking from the opposite side of the leaving group. The product from this type of reaction can be cyclohexanol.
elimination reaction
Elimination reactions involve the removal of a proton and a leaving group, resulting in the formation of a double bond. When bromocyclohexane reacts with hydroxide ion, an elimination (E2) reaction can occur. In this scenario, OH鈦� abstracts a 尾-proton while the bromine leaves, resulting in the formation of cyclohexene. Elimination reactions can proceed through E1 or E2 mechanisms, but E2 is more common in the presence of strong bases and less sterically hindered conditions. The major product of this reaction, due to the favorability of the E2 mechanism, is cyclohexene, an alkene with a double bond in a cyclohexane ring.
