What is the definition of a nucleophile?

A nucleophile is an electron-pair donator.


A nucleophile is an electron-rich species that donates a pair of electrons in a reaction. Examples of nucleophiles include OH-, CN- and Br-.

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What happens to the halogen atom when a halogenoalkane undergoes nucleophilic substitution?

The halogen atom is replaced by a nucleophile.

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Describe, and give the ionic equation for, the reaction of halogenoalkanes (RX) with aqueous alkali (OH-).

Halogenoalkanes are warmed with aqueous alkali to produce an alcohol. A hydrolysis reaction occurs.


RX + OH- ➔ ROH + X-

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Explain the role of OH- in the nucleophilic substitution reaction mechanism of halogenoalkanes.

The OH- ion acts as the nucleophile, donating a pair of electrons to the carbon atom bonded to the halogen.


This breaks the carbon-halogen bond and forms a new carbon-oxygen bond.

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What type of bond fission (homolytic or heterolytic) occurs in a nucleophilic substitution reaction of a halogenoalkane?

Heterolytic fission


The bond breaks to give a halide ion and a carbocation.

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Describe, and give an equation for, the reaction of halogenoalkanes (RX) with cyanide ions, CN-.

Halogenoalkanes are heated in a solution of potassium cyanide in ethanol to form nitriles.


RX + CN- ➔ RCN + X-

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What is the reaction mechanism for the reaction above?

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Describe, and give an equation for, the reaction of halogenoalkanes with excess concentrated ammonia, NH3.

Halogenoalkanes (RX) are heated under pressure in a solution of excess concentrated ammonia in ethanol to form primary amines.


RX + 2NH3 ➔ RNH2 + NH4X

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What is the mechanism for the reaction above?

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