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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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Most popular questions from this chapter

Show how you would accomplish the following synthesis.

(a) Acetphenone→ acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol →2-hydroxyheptanoic acid

The following road-map problem centers on the structure and properties of A, a key intermediate in these reactions. Give structures for compounds A through J.

In the absence of water, ophthalaldehyde has the structure shown. Its strong IR absorption is at 1687 cm-1; the proton NMR data are shown by the structure. In the presence of water, a new compound is formed that has a strong IR absorption around 3400 cm-1 and no absortion in the C=0 region. propose a structure of X consistent with this information and suggest how X consistent with this information and suggest how X was formed.

Sketch the expected proton NMR spectra of 3,3- dimethylbutanal.

Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
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