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Draw the structure of the product that is formed when the compound shown below undergoes an...

Draw the structure of the product that is formed when the compound shown below undergoes an elimination reaction with NaOCH3.


Draw the structure of the product that is formed when the compound shown below undergoes an elimination reaction with NaOCH3. Indicate the stereochemistry of the product.
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Concepts and reason

The reaction of a haloalkane is given with sodium methoxide. The sodium methoxide is a strong base and thus favors elimination product to form alkenes. The mode of elimination is E2.

Fundamentals

The reaction will take place via E2 mechanism because the base used is a strong base and the alkyl halide is a secondary halide.

E2 reaction: It stands for elimination reaction following second order kinetics. In E2 reaction, the base abstracts the β\beta hydrogen and removal of the leaving group simultaneously in the same step. A general mechanism is shown below:

Н
Н
B
ВН
+
+
CH2
R2
H
X is the leaving group
B is the base

The elimination taking place via anti mode where the leaving group and the hydrogen abstracted by base are on the opposite sides or anti periplanar.

The required structure is as follows:

CHн
Hас
На
Cнз
Br
н
CHз

The product of the reaction is as follows:

CH3
Н.с — сHз
НаС — сн2
Hас
н
На
NaOCH3
-СH
CНз
Н
н
CH3
Br

Ans:

The product of the reaction is as follows:

CH2
Hас — сНз
CH3
I

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