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Chapter 21: 34P (page 817)

Identify the acetal in oleandrin, and draw the products formed by acid-catalysed hydrolysis of the acetal.

Short Answer

Expert verified

Acetal group is at C-3 carbon atom of the oleandrin.

Step by step solution

01

Protecting group

The conversion of the functional group of a compound to specify the chemoselective center of reaction is referred to as protection of the compound.

02

Hydrolysis

Any acetal group would hydrolyze in an acidic medium to form the corresponding carbonyl compound and alcohol.

The hydrolysis of Oleandrin is as follows,

Hydrolysis of Oleandrin

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Most popular questions from this chapter

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

How would you use a protecting group to carry out the following transformation?

Besides the tert-butyldimethylsilyl ethers introduced in Chapter 20, there are many other widely used alcohol protecting groups. For example, an alcohol such as cyclohexanol can be converted to a methoxy methyl ether (a MOM protecting group) by treatment with base and chloromethyl methyl ether, . The protecting group can be removed by treatment with aqueous acid.

a. Write a stepwise mechanism for the formation of a MOM ether from cyclohexanol.

b. What functional group comprises a MOM ether?

c. Besides cyclohexanol, what other products are formed by aqueous hydrolysis of the MOM ether? Draw a stepwise mechanism that accounts for formation of each product.

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.

Give the IUPAC name for each aldehyde.

a.

b.

c
See all solutions

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