What is the product of the reaction of ethyl bromide with...

What is the product of the reaction of ethyl bromide with each of the following nucleophiles?
a. $\mathrm{CH}_{3} \mathrm{OH}$
b. $^{-} N_{3}$
c. $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}$
d. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{S}^{-}$

Key Concepts

Alkylation Reactions

Alkylation reactions involve the transfer of an alkyl group from one molecule to another, typically through a substitution reaction. With ethyl bromide, the nucleophile attacks the ethyl group, resulting in products where the ethyl moiety is attached to the incoming nucleophile, thereby forming new organic compounds such as ethers, azides, quaternary ammonium salts, or thioethers depending on the nature of the nucleophile.

Leaving Group Ability

Leaving group ability is a measure of how readily a group can depart from the substrate, taking its bonding electron pair with it. In alkyl halides, bromide ion is a common leaving group because it is relatively stable once detached, which facilitates the substitution reaction processes in SN2 mechanisms.

Nucleophilicity

Nucleophilicity refers to the tendency of a chemical species to donate an electron pair and form a new chemical bond. In the context of alkyl halide reactions, varying strengths of nucleophiles (like alcohols, azide ions, amines, and thiolates) influence the rate of the SN2 reaction and determine what type of substitution or addition product is formed.

SN2 Reaction Mechanism

The SN2 reaction mechanism involves a one-step, bimolecular process where the nucleophile attacks the backside of the substrate, leading to simultaneous bond formation with the nucleophile and bond breaking with the leaving group. This mechanism is especially relevant for primary alkyl halides, such as ethyl bromide, due to their low steric hindrance which facilitates the nucleophilic attack.

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