Chapter 21: 67P (page 817)
Draw a stepwise mechanism for each reaction.
a.
b.
Short Answer
a.
b.
Chapter 21: 67P (page 817)
Draw a stepwise mechanism for each reaction.
a.
b.
a.
b.
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Get started for freeDraw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.
Which compound forms the higher concentration of hydrate at equilibrium, PhCOCHO or PhCH2CHO ? Explain your reasoning.
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.
Identify the acetal in oleandrin, and draw the products formed by acid-catalysed hydrolysis of the acetal.
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
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