Chapter 21: 51P (page 817)
What hydrolysis products are formed when the following compound is treated with aqueous acid?
Chapter 21: 51P (page 817)
What hydrolysis products are formed when the following compound is treated with aqueous acid?
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Get started for freeWhat carbonyl compound and amine or alcohol are needed to prepare each product?
a.
b.
c.
d.
Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).
a. Which carbonyl compound is more stable?
b. Which compound forms the higher percentage of hydrate at equilibrium?
c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?
Explain your reasoning in each part.
What lactol (cyclic hemiacetal) is formed from intramolecular cyclization of each hydroxy aldehyde?
a.
b.
Draw the products of each reaction.
a.
b.
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.
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