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Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The mechanism shown for the reaction are given below:-

Step by step solution

01

Type of the reagents used

Strong bases such as hydroxides and ethoxides favor a mixture of both E2 and SN2 reactions, while bulky bases like sodium or potassium tert-butoxide predominantly favor E2 reactions.

As a weak base and a weak nucleophile CH3OH are used here, it promotes a mixture of E2 and SN2.

02

Mechanism

The reaction proceeds in a SN1 mechanism, and a positive charge develops on the carbon atom. The lone pair of oxygen attacks the carbon-containing a positive charge and gets attached to that position.

The reaction also proceeds via the E1 mechanism and attacks the terminal hydrogen atom by which the bromine departs from the substrate. A double bond is formed, and hydrogen bromide is obtained as a side product.

Based on the explanations, the mechanism shown for the given reaction are:-

A detailed reaction scheme

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