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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

Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.

Rank the following compounds in order of increasing amount of hydrate present at equilibrium.

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH3COCH2Br BrCH2CHO鈥�鈥�鈥�鈥�鈥�鈥�CH2O鈥�鈥�鈥�鈥�鈥�鈥�CH3COCH3鈥�鈥�鈥�鈥�鈥�鈥�CH3CHO

Predict the major products of the following reactions:

(a) (b)

(c) (d)

Sodium triacetoxyborohydride, NaBHOAc3, is a mild reducing agent that reduces aldehydes more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.
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