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Nucleophilic Displacement Reactions

Nucleophilic displacement reactions are a type of chemical reaction in which a nucleophile (a species with a lone pair of electrons) attacks an electrophile (a species with a positive charge or a partial positive charge) and replaces a leaving group.

Three Nucleophilic Displacement Reactions

Reactants	Products	Reaction Conditions
CH3Br + NaOH →	CH3OH + NaBr	Aqueous solution
(CH3)3CBr + NH3 →	(CH3)3CNH2 + HBr	Alcoholic solution
C6H5Cl + CH3ONa →	C6H5OCH3 + NaCl	Ether solution

Reaction Mechanisms

• SN2 Reaction:In an SN2 reaction, the nucleophile attacks the electrophile in a concerted manner, resulting in inversion of configuration at the electrophilic carbon.
• SN1 Reaction:In an SN1 reaction, the electrophile first ionizes to form a carbocation, which is then attacked by the nucleophile. This results in a mixture of products, including both inverted and retained configurations.
• E2 Reaction:In an E2 reaction, the base abstracts a proton from the carbon adjacent to the electrophilic carbon, resulting in the formation of an alkene.

Factors Affecting Nucleophilicity

• Charge:Nucleophiles with a negative charge are generally more nucleophilic than those with a neutral or positive charge.
• Size:Smaller nucleophiles are generally more nucleophilic than larger nucleophiles.
• Polarizability:Nucleophiles with a polarizable electron cloud are generally more nucleophilic than those with a non-polarizable electron cloud.
• Solvation:Nucleophiles that are strongly solvated are generally less nucleophilic than those that are weakly solvated.

Stereochemistry of Nucleophilic Displacement Reactions

The stereochemistry of a nucleophilic displacement reaction depends on the type of reaction mechanism. In an SN2 reaction, the nucleophile attacks the electrophile in a concerted manner, resulting in inversion of configuration at the electrophilic carbon. In an SN1 reaction, the electrophile first ionizes to form a carbocation, which is then attacked by the nucleophile.

This results in a mixture of products, including both inverted and retained configurations.

Applications of Nucleophilic Displacement Reactions

• Alkylation of Alcohols and Phenols:Nucleophilic displacement reactions are used to alkylate alcohols and phenols, which is a common step in the synthesis of ethers and esters.
• Acylation of Amines:Nucleophilic displacement reactions are used to acylate amines, which is a common step in the synthesis of amides.
• Substitution of Halogens:Nucleophilic displacement reactions are used to substitute halogens with other functional groups, which is a common step in the synthesis of many organic compounds.

General Inquiries: A Set Of Three Nucleophilic Displacement Reactions Is Shown Below

What are nucleophilic displacement reactions?

Nucleophilic displacement reactions are a type of chemical reaction in which a nucleophile attacks an electrophile, resulting in the displacement of a leaving group.

What are the three nucleophilic displacement reactions shown below?

The three nucleophilic displacement reactions shown below are:

1. SN2 reaction: A nucleophile attacks an electrophile at the back side, resulting in inversion of configuration.
2. SN1 reaction: A nucleophile attacks a carbocation, resulting in racemization.
3. E2 reaction: A base abstracts a proton from a carbon adjacent to the electrophile, resulting in the formation of an alkene.

What are the factors that affect nucleophilicity?

The factors that affect nucleophilicity include:

• Charge: Nucleophiles with a negative charge are more nucleophilic than nucleophiles with a neutral or positive charge.
• Size: Nucleophiles with a smaller size are more nucleophilic than nucleophiles with a larger size.
• Polarizability: Nucleophiles with a higher polarizability are more nucleophilic than nucleophiles with a lower polarizability.