What is the product of the reaction of bromoethane with each of the following nucleophiles?
a. CH₃CH₂CH₂O⁻
b. CH₃C≡C⁻

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Step 1: Recognize the type of reaction. The reaction of bromoethane (CH3CH2Br) with nucleophiles typically proceeds via an SN2 mechanism because bromoethane is a primary alkyl halide. In an SN2 reaction, the nucleophile attacks the electrophilic carbon (attached to the bromine) in a single concerted step, displacing the bromine as a leaving group.

Step 2: Analyze the first nucleophile (CH3CH2CH2O−). This is a strong nucleophile (an alkoxide ion). It will attack the electrophilic carbon in bromoethane, leading to the substitution of the bromine atom with the ethoxy group (CH3CH2CH2O−). The product will be CH3CH2CH2OCH2CH3 (propoxyethane).

Step 3: Analyze the second nucleophile (CH3C≡C−). This is an acetylide ion, which is also a strong nucleophile. It will similarly attack the electrophilic carbon in bromoethane, displacing the bromine atom. The product will be CH3C≡CCH2CH3 (butyne).

Step 4: Consider the stereochemistry. Since the SN2 mechanism involves a backside attack, the configuration of the carbon center (if it were chiral) would invert. However, in this case, bromoethane is not chiral, so stereochemistry is not a concern.

Step 5: Summarize the products. For part (a), the product is propoxyethane (CH3CH2CH2OCH2CH3). For part (b), the product is butyne (CH3C≡CCH2CH3). These products result from the substitution of bromine with the respective nucleophiles.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, forming a chemical bond. Strong nucleophiles, such as alkoxide ions (like CH3CH2CH2O−), are more likely to react with electrophiles like bromoethane. The strength of a nucleophile is influenced by factors such as charge, electronegativity, and steric hindrance.

Substitution Reactions

Substitution reactions involve the replacement of one functional group in a molecule with another. In the case of bromoethane, the bromine atom can be replaced by a nucleophile through either an SN1 or SN2 mechanism, depending on the structure of the nucleophile and the substrate. Understanding these mechanisms is crucial for predicting the products of the reaction.

Alkyl Halides

Alkyl halides, such as bromoethane, are organic compounds containing a carbon-halogen bond. They are key substrates in nucleophilic substitution reactions. The reactivity of alkyl halides is influenced by the type of halogen, the carbon's hybridization, and the presence of steric factors, which can affect the pathway of the reaction with nucleophiles.

What is the product of the reaction of bromoethane with each of the following nucleophiles?a. CH3CH2CH2O− b. CH3C≡C−