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Chapter 25: 56 (page 1044)

What is the major Hofmann elimination product formed from each amine?

a

b

c

Short Answer

Expert verified

a

Major product of a.

b

Major product of b.

c

Major Pproduct of c.

Step by step solution

01

Hofmann elimination

It is the only possible way of converting 1° amines into a better leaving group. The 1° amine is converted into a quaternary ammonium salt before undergoing β-elimination.

02

Conditions for Hofmann elimination reaction

The reaction consists of 3 steps, all of which take place in one single step.

The reaction takes place via an anti-periplanar geometry, according to which the hydrogen atom and the amine group should be present on the opposite sides of the molecule.

03

Mechanism of the given reaction

The C-C bonds are rotated in the given molecules to obtain the anti geometry of the hydrogen atom and the amine group.

a

The given structure already has hydrogen and amine group anti to each other. Hence, the product of the reaction is given hereunder.

Product of a.

b

The C-C bond is rotated 120° counterclockwise. The product of the reaction is given hereunder.

Product of b.

c

The C-C bond is rotated 120°counterclockwise. The product of the reaction is given hereunder.

Product of c.

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