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Chapter 18: Q69P (page 973)

Show a complete mechanism for this equilibrium established in diethyl ether with HCl gas as catalyst.

Short Answer

Expert verified

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the nitrogen atom takes place at first.

(b) One of the lone pair on oxygen atom attacks the carbon of double bond, where the double bond gets rearranged.

(c) A chloride anion from attacks the hydrogen present on the hydroxy group which gives the desired product.

Step by step solution

01

Mechanism

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the nitrogen atom takes place at first.

(b) One of the lone pair on oxygen atom attacks the carbon of double bond, where the double bond gets rearranged.

(c) A chloride anion from attacks the hydrogen present on the hydroxy group which gives the desired product.

02

Mechanistic pathway

The complete mechanism for the reaction

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Solving the following road-map problem depends on determining the structure of A, the key intermediate. Give structures for compounds A through K.

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