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Chapter 18: Q69P (page 912)

Question: Show a complete mechanism for this equilibrium established in diethyl ether with HCI 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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Most popular questions from this chapter

Draw the structures of the following derivatives.

(a) the 2,4-dinitrophenylhydrazone of acetone

(b) the semicarbazone of cyclopentanone

(c) cyclcobuanone oxime

(d) the ethylene acetal of hexan-2-one

(e) acetaldehyde diethyl acetal

(f) the ethyl hemiacetal of acetaldehyde

(g) the (Z) isomer of the ethyl imine of propiophenone

(h) the hemiacetal form of 6-hydroxyhexanal

Propose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give benzaldehyde dimethyl acetal.

For each compound,

  1. Name the functional group,
  2. Show what compounds result from complete hydrolysis.

Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone dimethyl acetal.

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts and show why this mechanism does not work for the other one.
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