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Chapter 21: 50P (page 817)

What products are formed when each acetal is hydrolyzed with aqueous acid?

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Acetal 

Compounds in which the two ether groups are connected to the same carbon can be designated as acetals. They can be generated from hemiacetals.

02

Hydrolysis of acetal

The resultant product of acetal hydrolysis is a carbonyl compound. The alkoxy group is transformed into a good leaving group in acetal hydrolysis.

03

Products formed when acetal is hydrolyzed with ester

The hydrolysis of the given acetal with aqueous acid leads to the formation of the compound 5-hydroxy-4-(hydroxymethyl)pentanal. The reaction can be given as:

Products formed by the hydrolysis of compound a

The product formed by the hydrolysis of compound b is 1,7-dihydroxyheptan-4-one. The hydrolysis of the acetal in the presence of aqueous acid can be given as:

Products formed by the hydrolysis of compound b

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Most popular questions from this chapter

Salsolinol is a naturally occurring compound found in bananas, chocolate, and several foods derived from plant sources. Salsolinol is also formed in the body when acetaldehyde, an oxidation product of the ethanol ingested in an alcoholic beverage, reacts with dopamine, a neurotransmitter. Draw a stepwise mechanism for the formation of salsolinol in the followingreaction.

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

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