Question

Draw the neutral organic starting material

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Concepts and reason

The product of a certain reaction is given and the reactant that is the starting material needs to be given. The reagent used is bromine in dichloromethane. Therefore, the starting material can be alkene which undergoes bromination followed by certain transformation to give the product.

Fundamentals

Retrosynthesis: It is a method that is used to obtain the starting material from the target molecule. Thus, it involves moving backward from the products to the reagents. It is represented by the arrow “ \Rightarrow ”.

Retrosynthesis involves disconnection of bonds to obtain the charged species (synthons). The synthons are unstable and hence, their synthetic equivalents are used to perform the function of a synthon.

Target molecule: it is the one whose synthesis needs to be carried out.

Disconnect the bond between the carbon and the oxygen as shown below:

E-
Br
Br
Synthon

Further, disconnect the bond between the carbon and bromine in the synthon formed as shown below:

+
Br*
Br
Synthon
Synthons
-OH
=
+
Brz
(A)
Synthetic equivalents

Explanation for the reaction is as follows:

Br2
CH,Cl2
Br
pent-4-en-1-01
(Starting material)
(Target molecule)

Ans:

The neutral starting material is as follows:

Br2
CH2Cl2

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