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Chapter 18: Q20. (page 945)

Propose a mechanism for the hydrolysis of benzaldehyde methyl imine just shown.

Short Answer

Expert verified

The mechanism for hydrolysis is shown below.

Step by step solution

01

Formation of Imine

The formation of imine is a reversible process. Most imines can be hydrolysed back into the amines and aldehydes or ketones.The mechanism for the process of hydrolysis of imine is generally the reverse of the mechanism for its formation.

02

Mechanism for the hydrolysis of Benzaldehyde Methyl Imine

The hydrolysis of benzaldehyde methyl imine to benzaldehyde can be shown by the reaction as shown below.

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Most popular questions from this chapter

Predict the products formed when cyclopentanecarbaldehyde reacts with the following reagents.

(a) PhMgBr, then H3O+

(b) Tollens reagent

(c) semicarbazide and weak acid

(d) excess ethanol and acid

(e) propane-1-3-diol, H+

(f) zinc amalgam and dilute hydrochloric acid

Predict the products of the following reactions.

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.

(a)

(b)

(c)

Show how would you accomplish the following syntheses. You may use whatever additional reagents you need.

(a)

(b)

(c)

(d)

(e)

(f)

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
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