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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

An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm-1 . The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H- NMR spectrum of D is shown below. What is the structure of D?

What carbonyl compound and alcohol are formed by hydrolysis of each acetal?

a.

b.

c.

Devise a synthesis of each compound from the given starting materials. You may also use organic alcohols having four or fewer carbons, and any organic or inorganic reagents

a)

b)

c)

Reaction of 5,5-dimethoxypentan-2-one with methylmagnesium iodide followed by treatment with aqueous acid forms cyclic hemiacetal Y. Draw a stepwise mechanism that illustrates how Y is formed

Use the 1 H NMR and IR data to determine the structure of each compound.
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