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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

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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

Rank the following compounds in order of increasing reactivity in nucleophilic addition

Draw a stepwise mechanism for the following reaction

Draw all stereoisomers formed in each reaction.

a.

b.

c.

d.

Show two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon鈥揷arbon bond with an organometallic reagent in one of the steps.

a.

b.

What Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.

a.

b.

c.
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