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Chapter 21: 29P (page 817)

Draw the products of each reaction.

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Acetal

Acetals form when “aldehydes and ketones” react with two equivalents of alcohols. A cyclic acetal forms when a diol such as ethylene glycol is used in place of two equivalents of alcohol.

02

Acetal formation

a. Cyclopentanone reacts with two equivalents of methanol to form an open acetal.

Product formation in reaction a.

b. Acetone reacts with ethylene glycol to form cyclic acetal.

Product formation in reaction 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?

Label each compound as an acetal, a hemiacetal, or an ether.

a.

b.

c.

d.

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.

Draw the products of each reaction.

a.

b.

What carbonyl compound and diol are needed to prepare each compound?

a.

b.
See all solutions

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