What is the product of the reaction of bromoethane with each of the following nucleophiles? c. (CH3)3N d. CH3CH2S-

Verified step by step guidance

1. Identify the type of reaction: Bromoethane is a primary alkyl halide, which typically undergoes S_N2 reactions with strong nucleophiles.
2. For part c, consider the nucleophile (CH₃)₃N: This is a tertiary amine, which can act as a nucleophile but is sterically hindered, potentially leading to a different reaction pathway such as elimination.
3. For part d, consider the nucleophile CH₃CH₂S^-: This is a strong nucleophile and a good candidate for an S_N2 reaction with bromoethane.
4. Predict the product for part c: If (CH₃)₃N acts as a nucleophile, it may lead to a quaternary ammonium salt, but steric hindrance might favor elimination instead.
5. Predict the product for part d: The S_N2 reaction with CH₃CH₂S^- will likely result in the substitution of the bromine atom with the ethylthio group, forming ethyl ethyl sulfide.

Key Concepts

Nucleophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair to form a chemical bond. Strong nucleophiles, such as (CH3)3N and CH3CH2S-, are typically negatively charged or have lone pairs that can be readily shared. Understanding nucleophilicity is crucial for predicting the outcome of nucleophilic substitution reactions, such as those involving bromoethane.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution mechanisms, primarily SN1 and SN2, describe how nucleophiles replace leaving groups in organic compounds. SN2 reactions involve a single concerted step where the nucleophile attacks the electrophile, while SN1 reactions proceed through a carbocation intermediate. The choice of mechanism affects the product distribution and stereochemistry of the reaction.

Leaving Group Ability

The leaving group ability is a measure of how easily a group can depart from a molecule during a reaction. Good leaving groups, such as bromide from bromoethane, stabilize the transition state and facilitate nucleophilic attack. The nature of the leaving group influences the reaction pathway and the overall rate of nucleophilic substitution.