Question

Make a new bond between a nucleophile and an electrophile. Reaction of the \(3^{7}\) carbocation (an electrophile) with bromide ion (a nucleophile) gives the alkyl halide. CC(C)(C)CBr CC(C)(Br)CC(C)(C)Br 2-Brome-2-rethylpropane (tert-Butyl bromide)

Short answer

Question: Describe the reaction between an electrophile and a nucleophile to form an alkyl halide, such as tert-Butyl bromide, and explain its formation and structure. Answer: The reaction between an electrophile (carbocation) and a nucleophile (bromide ion) involves a process called nucleophilic attack, in which the nucleophile donates a pair of electrons to the electrophile. This forms a bond between them, ultimately resulting in an alkyl halide like tert-Butyl bromide. The structure of tert-Butyl bromide is represented by the SMILES notation: CC(C)(Br)CC(C)(C)Br.

Step-by-step solution

Identifying the reactants

The two reactants in this reaction are the carbocation (\(3^7\)) and the bromide ion (Br-). The carbocation acts as the electrophile, which is a molecule that can accept a pair of electrons. The bromide ion (Br-) acts as the nucleophile, a molecule that can donate a pair of electrons.

Nucleophilic attack

The nucleophile (bromide ion, Br-) donates a pair of electrons to the electrophile (carbocation), forming a bond between them. As a result, the positively charged carbon atom in the carbocation forms a bond with the negatively charged bromide ion.

Formation of the alkyl halide

The bond between the carbocation and the bromide ion forms the desired product, an alkyl halide. In this case, the product is 2-bromo-2-methylpropane, also known as tert-Butyl bromide. Its structure is represented by the SMILES notation: CC(C)(Br)CC(C)(C)Br.

Visually representing the product

The final structure of the tert-Butyl bromide after the reaction is as follows: CC(C)(Br)CC(C)(C)Br

Key concepts

Nucleophile

A nucleophile is a chemical species that loves to donate electrons. The name tells us this: "nucleo" means "nucleus loving." Since nuclei are positively charged, nucleophiles are typically negatively charged or neutral molecules with a lone pair of electrons ready to give.
One of the most common nucleophiles in organic reactions is the bromide ion, denoted as Br-. In the given reaction, the bromide ion uses its extra electrons to attack a positively charged species, forming a new bond.
When thinking about nucleophiles, remember that they look for centers of positive charge, like carbocations, to form a stable bond. This is a fundamental behavior in many organic reactions, where electron-rich areas seek out electron-poor areas.

Electrophile

In contrast to a nucleophile, an electrophile is an electron-deficient species that seeks out electrons. The term "electrophile" comes from "electron loving," indicating that these species are charged or electron-poor and want to accept electron pairs from nucleophiles.
In our reaction example, the tert-butyl carbocation serves as the electrophile. It has a positively charged carbon center, making it highly attractive to the nucleophile, bromide ion.
Understanding electrophiles is key to many chemical reactions, especially in organic chemistry, where reactions often happen around these electron-poor regions. Electrophilic sites can be found in many functional groups, making them crucial in the formation of new chemical bonds.

Alkyl Halide

An alkyl halide is an organic molecule containing one or more halogen atoms (like fluorine, chlorine, bromine, or iodine) attached to an alkyl group. The general formula for an alkyl halide is R-X, where R represents the alkyl group and X represents the halogen.
In this reaction, tert-butyl bromide is the alkyl halide produced. This type of compound is crucial in organic synthesis and used in various industrial applications.
Alkyl halides are known for their reactivity, due to the polar carbon-halogen bond. This bond makes them susceptible to reactions with nucleophiles and bases, leading to a range of chemical transformations. Understanding how they react is a vital part of mastering organic chemistry.

tert-Butyl Bromide

Tert-butyl bromide is a specific type of alkyl halide, the product of our reaction, and is also known as 2-bromo-2-methylpropane. It has an interesting structural feature: a central carbon atom bonded to three methyl groups and a bromide ion.
Its structure is represented in SMILES notation as: CC(C)(Br)CC(C)(C)Br. This visualization helps chemists understand the spatial arrangement of atoms and plan reactions efficiently.
Tert-butyl bromide is not only a cornerstone reactant in laboratory studies but also an important intermediate in synthesizing other compounds. Its formation via nucleophilic attack showcases the dynamic nature of electrophilic reactions, providing insight into the fascinating world of organic chemistry.