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Chapter 21: 12P (page 817)

What reagents are needed to convert each compound into butanal (CH3CH2CH2CHO )?

a.

b.

c.

Short Answer

Expert verified

a)

b)

c)

Step by step solution

01

Gilman’s reagent

Gilman’s reagent is used to form carbon-carbon bonds in organic reactions or synthesis.

02

Formation of the product

a)

The reaction of benzene with acetyl chloride in the presence of aluminum trichloride gives acetophenone.

The reaction is shown below.

Synthesis in a

b)

The reaction of benzoyl chloride with Gilman’s reagent in the presence of water gives acetophenone.

The reaction is shown below.

Synthesis in b

c)

The reaction of ethynylbenzene water in the presence of sulfuric acid and mercuric sulfate gives acetophenone.

The reaction is shown below.

Synthesis in c

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Most popular questions from this chapter

Give the IUPAC name for each ketone

a.

b

c

Design a stepwise synthesis to convert cyclopentanone and 4-bromobutanal to hydroxy aldehyde A.

What 1° amine and carbonyl compound are needed to prepare each imine?

a.

b.

Give the IUPAC name for each aldehyde.

a.

b.

c

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.
See all solutions

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