Question

Show each arrow pushing mechanisms between silver nitrate in ethanol with each of the following alkyl halides: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, bromocyclohexane, bromobenzene, and α-bromotoluene

Answer 1

The Silver Nitrate Test allows for the identification of alkyl halides by observing them in an alcoholic silver
nitrate environment.

The rate at which the silver halide salt precipitate forms is characteristic of different
types of alkyl halides.

Organic halides may react with ethanol to form ethyl ethers.

When the ethanol contains silver ion, the rate of reaction increases because the silver ion acts as an electrophile toward the halogen and helps to break the carbon-halogen bond.

Alkyl chlorides yield an observable silver chloride precipitate, which is insoluble in ethanol and thus provides a indicator that a reaction has occurred.

In this case, the reaction mechanism is SN1.

The slow step being the breaking of the carbon-halogen bond.
The carbocation then reacts rapidly with alcohol to form the ether.

Tertiary, allylic, and benzylic alcohols react very quickly,

while secondary alkyl halides react fairly quickly.

Primary as well as aryl, alkenyl (vinyl), and alkynyl halides do not react at all.